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Tailor-made amino acid-derived pharmaceuticals approved by the FDA in 2019

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Abstract

Amino acids (AAs) are among a handful of paramount classes of compounds innately involved in the origin and evolution of all known life-forms. Along with basic scientific explorations, the major goal of medicinal chemistry research in the area of tailor-made AAs is the development of more selective and potent pharmaceuticals. The growing acceptance of peptides and peptidomimetics as drugs clearly indicates that AA-based molecules become the most successful structural motif in the modern drug design. In fact, among 24 small-molecule drugs approved by FDA in 2019, 13 of them contain a residue of AA or di-amines or amino-alcohols, which are commonly considered to be derived from the parent AAs. In the present review article, we profile 13 new tailor-made AA-derived pharmaceuticals introduced to the market in 2019. Where it is possible, we will discuss the development form drug-candidates, total synthesis, with emphasis on the core-AA, therapeutic area, and the mode of biological activity.

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References

  • Aceña JL, Sorochinsky AE, Moriwaki H, Sato T, Soloshonok VA (2013) Synthesis of fluorine-containing α-amino acids in enantiomerically pure form via homologation of Ni(II) complexes of glycine and alanine Schiff bases. J Fluorine Chem 155:21–38

    Google Scholar 

  • Aceña JL, Sorochinsky AE, Soloshonok VA (2014) Asymmetric synthesis of α-amino acids via homologation of Ni(II) complexes of glycine Schiff bases. Part 3: Michael addition reactions and miscellaneous transformations. Amino Acids 46:2047–2073

    PubMed  Google Scholar 

  • Alexander TB, Lacayo NJ, Choi JK, Ribeiro RC, Pui CH, Rubnitz JE (2016) Phase I study of selinexor, a selective inhibitor of nuclear export, in combinationwith fludarabine and cytarabine, in pediatric relapsed or refractory acute leukemia. J Clin Oncol 34:4094–4101

    CAS  PubMed  PubMed Central  Google Scholar 

  • Al-Salama ZT (2019b) Siponimod: first global approval. Drugs 79:1009–1015

    CAS  PubMed  Google Scholar 

  • Al-Salama ZT, Keam SJ (2019a) Entrectinib: first global approval. Drugs 79:1477–1483

    PubMed  Google Scholar 

  • Amatu A, Somaschini A, Cerea G, Bosotti R, Valtorta E, Buonandi P, Marrapese G, Veronese S, Luo D, Hornby Z, Multani P, Murphy D, Shoemaker R, Lauricella C, Giannetta L, Maiolani M, Vanzulli A, Ardini E, Galvani A, Isacchi A, Sartore-Bianchi A, Siena S (2015) Novel CAD-ALK gene rearrangement is drugable by entrectinib in colorectal cancer. Brit J Cancer 113:1730–1734

    CAS  PubMed  PubMed Central  Google Scholar 

  • Bahleda R, Italiano A, Hierro C, Mita A, Cervantes A, Chan N (2019) Multicenter Phase I study of erdafitinib (JNJ-42756493), oral pan-fibroblast growth factor receptor inhibitor, in patients with advanced or refractory solid tumors. Clin Cancer Res 25:4888–4897

    CAS  PubMed  Google Scholar 

  • Baladi MG, Forster MJ, Gatch MB, Mailman RB, Hyman DL, Carter LP, Janowsky A (2018) Characterization of the neurochemical and behavioral effects of solriamfetol (JZP-110), a selective dopamine and norepinephrine reuptake inhibitor. J Pharmacol Exp Ther 366:367–376

    CAS  PubMed  Google Scholar 

  • Bell IM, Fraley ME. Bell IM, Fraley ME (2013) Piperidinone carboxamide azaindane CGRP receptor antagonists. U.S. Patent 8481556

  • Belokon YN, Zeltzer IE, Bakhmutov VI, Saporovskaya MB, Ryzhov MG, Yanovsky AI, Struchkov YT, Belikov VM (1983) Asymmetric synthesis of threonine and partial resolution and retroracemization of alpha.-amino acids via copper(II) complexes of their Schiff bases with (S)-2-N-(N’-benzylprolyl)aminobenzaldehyde and (S)-2-N-(N’-benzylprolyl)aminoacetophenone. Crystal and molecular structure of a copper(II) complex of glycine Schiff base with (S)-2-N-(N′-benzylprolyl)aminoacetophenone. J Am Chem Soc 105:2010–2017

    CAS  Google Scholar 

  • Belokon YN, Bulychev AG, Vitt SV, Struchkov YT, Batsanov AS, Timofeeva TV, Tsyryapkin VA, Ryzhov MG, Lysova LA (1985a) General method of diastereo- and enantioselective synthesis of β-hydroxy-α-amino acids by condensation of aldehydes and ketones with glycine. J Am Chem Soc 107:4252–4259

    CAS  Google Scholar 

  • Belokon YN, Chernoglazova NI, Kochetkov CA, Garbalinskaya NS, Belikov VM (1985b) Preparation of optically pure α-methyl-α-amino acids via alkylation of the nickel(II) Schiff base of (R, S)-alanine with (S)-2-N-(N′-benzylprolyl)aminobenzaldehyde. J Chem Soc Chem Commun 3:171–172

    Google Scholar 

  • Bera K, Namboothiri I (2014) Asymmetric synthesis of quaternary α-amino acids and their phosphonate analogues. Asian J Org Chem 3:1234–1260

    CAS  Google Scholar 

  • Blair HA (2020) Lumateperone: first approval. Drugs 80:417–423

    PubMed  Google Scholar 

  • Blalr HA (2019) Fedratinib: first approval. Drugs 19:1719–1725

    Google Scholar 

  • Borthwick AD (2012) 2,5-Diketopiperazines: synthesis, reactions, medicinal chemistry, and bioactive natural products. Chem Rev 112:3641–3716

    CAS  PubMed  Google Scholar 

  • Briard E, Rudolph B, Desrayaud S, Krauser JA, Auberson YP (2015) MS565: A SPECT tracer for evaluating the brain penetration of BAF312 (siponimod). ChemMedChem 10:1008–1018

    CAS  PubMed  Google Scholar 

  • Byrd JC, Harrington BH, O’Brien S, Jones JA, Schuh AS, Devereux S, Chaves J, Wierda WG, Awan FT, Brown JR, Hillmen P, Stephens DM, Ghia P, Barrientos JC, Pagel JM, Woyach J, Johnson D, Huang J, Wang X, Kaptein A, Lannutti BJ, Covey T, Fardis M, McGreivy J, Hamdy A, Rothbaum W, Izumi R, Diacovo TG, Johnson AJ, Furman RR (2016) Acalabrutinib (ACP-196) in relapsed chronic lymphocytic leukemia. N Engl J Med 374:323–332

    CAS  PubMed  Google Scholar 

  • Cao JJ, Hood J, Lohse D, Mak CC, Mc Pherson A, Noronha G, et al (2007) Bi-aryl meta-pyrimidine inhibitors of kinases. WO2007053452

  • Caravatti G, Fairhurst RA, Furet P, Guagnano V, Imbach P (2010) PCT Int. Appl. WO2010029082

  • Cativiela C, Ordóñez M, Viveros-Ceballos JL (2020) Stereoselective synthesis of acyclic α, α-disubstituted α-amino acids derivatives from amino acids templates. Tetrahedron 76:130875

    CAS  Google Scholar 

  • Chaudhry BZ, Cohen JA, Conway DS (2017) Sphingosine 1-phosphate receptor modulators for the treatment of multiple sclerosis. Neurotherapeutics 14:859–873

    CAS  PubMed  PubMed Central  Google Scholar 

  • Chen X, Xu L, Liu W (2017) Novel synthesis method of Selinexor active pharmaceutical ingredient. CN106831731

  • Choi YM, Byun JK (1996) Novel phenylalkylaminoalcohol carbamates and process for preparing the same. PCT Int Appl. WO1996007637

  • Correll CU, Davis RE, Weingart M, Saillard J, O’Gorman C, Kane JM, Lieberman JA, Tamminga CA, Mates S, Vanover KE (2020) Efficacy and safety of lumateperone for treatment of schizophrenia: a randomized clinical trial. JAMA Psychiatry 77:349–358

    PubMed  PubMed Central  Google Scholar 

  • D'Arrigo P, Cerioli L, Fiorati A, Servi S, Viani F, Tessaroa D (2012a) Naphthyl-l-α-amino acids via chemo-enzymatic dynamic kinetic resolution. Tetrahedron Asymmetry 23:938–944

    CAS  Google Scholar 

  • D'Arrigo P, Cerioli L, Servi S, Viani F, Tessaroa D (2012b) Synergy between catalysts: enzymes and bases. DKR of non-natural amino acids derivatives. Cat Sci Technol 2:1606–1616

    CAS  Google Scholar 

  • Dauvilliers Y, Bassetti C, Lammers GJ, Arnulf I, Mayer G, Rodenbeck A, Lehert P, Ding CL, Lecomte JM, Schwartz JC (2013) Pitolisant versus placebo or modafinil in patients with narcolepsy: a double-blind, randomised trial. Lancet Neurol 12:1068–1075

    CAS  PubMed  Google Scholar 

  • Davis RE, Vanover KE, Zhou Y, Brašić JR, Guevara M, Bisuna B, Ye W, Raymont V, Willis W, Kumar A, Gapasin L, Goldwater DR, Mates S, Wong DF (2015) ITI-007 demonstrates brain occupancy at serotonin 5-HT2A and dopamine D2 receptors and serotonin transporters using positron emission tomography in healthy volunteers. Psychopharmacology 232:2863–2872

    CAS  PubMed  Google Scholar 

  • Dodick DW, Lipton RB, Ailani J, Lu K, Finnegan M, Trugman JM, Szegedi A (2019) Ubrogepant for the treatment of migraine. N Engl J Med 381:2230–2241

    CAS  PubMed  Google Scholar 

  • Duggan S, Keam SJ (2019) Upadacitinib: first approval. Drugs 79:1819–1828

    PubMed  Google Scholar 

  • Ellis TK, Martin CH, Tsai GM, Ueki H, Soloshonok VA (2003a) Efficient synthesis of sterically constrained symmetrically α, α-disubstituted α-amino acids under operationally convenient conditions. J Org Chem 68:6208–6214

    CAS  PubMed  Google Scholar 

  • Ellis TK, Hochla VM, Soloshonok VA (2003b) Efficient synthesis of 2-aminoindane-2-carboxylic acid via dialkylation of nucleophilic glycine equivalent. J Org Chem 68:4973–4976

    CAS  PubMed  Google Scholar 

  • Ellis TK, Ueki H, Yamada T, Ohfune Y, Soloshonok VA (2006) The design, synthesis and evaluation of a new generation of modular nucleophilic glycine equivalents for the efficient synthesis of sterically constrained α-amino acids. J Org Chem 71:8572–8578

    CAS  PubMed  Google Scholar 

  • Erb B, Gallou IS, Kleinbeck FK (2012) Synthesis of 2-carboxamide cycloamino urea derivatives. PCT Int Appl. WO2012117071

  • Evans EC, Tester R, Aslanian S, Karp R, Sheets M, Labenski MT, Witowski SR, Lounsbury H, Chaturvedi P, Mazdiyasni H, Zhu Z, Nacht M, Freed MI, Petter RC, Dubrovskiy A, Singh J, Westllin WF (2013) Inhibition of BTKk with CC-292 provides early pharmacodynamic assessment of activity in mice and humans. J Pharmacol Exp Ther 346:219–228

    CAS  PubMed  Google Scholar 

  • Ferroni C, Pepe A, Kim YS, Lee S, Guerrini A, Parenti MD, Tesei A, Zamagni A, Cortesi M, Zaffaroni N, Cesare MD, Beretta GL, Trepel JB, Malhotra SV, Varchi G (2017) 1,4-Substituted triazoles as nonsteroidal anti-androgens for prostate cancer treatment. J Med Chem 60:3082–3093

    CAS  PubMed  PubMed Central  Google Scholar 

  • Fizazi K, Massard C, Bono P, Jones R, Kataja V, James N, Garci JA, Protheroe A, Tammela TL, Elliott T, Mattila L, Aspegren J, Vuorela A, Langmuir P, Mustonen M (2014) Activity and safety of ODM-201 in patients with progressive metastatic castration-resistant prostate cancer (ARADES): an open-label phase 1 dose-escalation and randomised phase 2 dose expansion trial. Lancet Oncol 5:975–985

    Google Scholar 

  • Frampton JE (2014) Pregabalin: a review of its use in adults with generalized anxiety disorder. CNS Drugs 28:835–854

    CAS  PubMed  Google Scholar 

  • Frankel M, Moses P (1960) Syntheses of amino alkyl sulphonic acids and their peptide analogues. Tetrahedron 9:289–294

    CAS  Google Scholar 

  • Furet P, Guagnano V, Fairhurst RA, Imbach-Weese P, Bruce I, Knapp M, Fritsch C, Blasco F, Blanz J, Aichholz R, Hamon J, Fabbro D, Caravatti G (2013) Discovery of NVP-BYL719 a potent and selective phosphatidylinositol-3 kinase alpha inhibitor selected for clinical evaluation. Bioorg Med Chem Lett 23:3741–3748

    CAS  PubMed  Google Scholar 

  • Gajofatto A (2017) Spotlight on siponimod and its potential in the treatment of secondary progressive multiple sclerosis: the evidence to date. Drug Des Dev Ther 11:3153

    CAS  Google Scholar 

  • Gergely P, Nuesslein-Hildesheim B, Guerini D, Brinkmann V, Traebert M, Bruns C, Pan S, Gray NS, Hinterding K, Cooke NG, Groenewegen A, Vitaliti A, Sing T, Luttringer O, Yang J, Gardin A, Wang N, Crumb WJ, Saltzman M, Rosengerg M, Wallström E (2012) The selective sphingosine 1-phosphate receptor modulator BAF312 redirects lymphocyte distribution and has species-specific effects on heart rate. Br J Pharmacol 167:1035–1047

    CAS  PubMed  PubMed Central  Google Scholar 

  • Gerspacher M, Fairhurst RA, Mah R, Roehn-Carnemolla E, Furet P, Fritsch C, Guthy DA (2015) Discovery of a novel tricyclic 4H-Thiazolo[5’,4’:4,5]pyrano[2,3-c]pyridine-2-amino scaffold and its application in a pi3kα inhibitor with high PI3K isoform selectivity and potent cellular activity. Bioorg Med Chem Lett 25:3582–3584

    CAS  PubMed  Google Scholar 

  • Giacomini MM, Hao J, Liang X, Chandrasekhar J, Twelves J, Whitney JA, Lepist EE, Ray AS (2017) Interaction of 2,4-diaminopyrimidine–containing drugs including fedratinib and trimethoprim with thiamine transporters. Drug Metab Dispos 45:76–85

    CAS  PubMed  Google Scholar 

  • Grygorenko OO, Biitseva AV, Zhersh S (2018) Amino sulfonic acids, peptidosulfonamides and other related compounds. Tetrahedron 74:1355–1421

    CAS  Google Scholar 

  • Guo Y (2014) Fused heterocyclic compounds as protein kinase inhibitors. WO2014173289

  • Guo YH, Liu Y, Hu N, Yu D, Zhou C, Shi G et al (2019) Discovery of zanubrutinib (BGB-3111), a novel, potent, and selective covalent inhibitor of Bruton’s tyrosine kinase. J Med Chem 62:7923–7940

    CAS  PubMed  Google Scholar 

  • Han J, Nelson DJ, Sorochinsky AE, Soloshonok VA (2011a) Self-disproportionation of enantiomers via sublimation; new and truly green dimension in optical purification. Curr Org Synth 8:310–317

    CAS  Google Scholar 

  • Han J, Sorochinsky AE, Ono T, Soloshonok VA (2011b) Biomimetic transamination-a metal-free alternative to the reductive amination. Application for generalized preparation of fluorine-containing amines and amino acids. Curr Org Synth 8:281–294

    CAS  Google Scholar 

  • Han J, Kitagawa O, Wzorek A, Klika KD, Soloshonok VA (2018) The self-disproportionation of enantiomers (SDE): a menace or an opportunity? Chem Sci 9:1718–1739

    CAS  PubMed  PubMed Central  Google Scholar 

  • Han J, Takeda R, Liu X, Konno H, Abe H, Hiramatsu T, Moriwaki H, Soloshonok VA (2019a) Preparative Method for asymmetric synthesis of (s)-2-amino-4,4,4-trifluorobutanoic acid. Molecules 24:4521

    CAS  PubMed Central  Google Scholar 

  • Han J, Wzorek A, Kwiatkowska M, Soloshonok VA, Klika KD (2019b) The self-disproportionation of enantiomers (SDE) of amino acids and their derivatives. Amino Acids 51:865–889

    CAS  PubMed  Google Scholar 

  • Han L, Li K, Xu H, Mei T, Sun Y, Qu J (2019c) N-TFA-Gly-Bt-based stereoselective synthesis of substituted 3-amino tetrahydro-2h-pyran-2-ones via an organocatalyzed cascade process. J Org Chem 84:10526–10534

    CAS  PubMed  Google Scholar 

  • He G, Wang B, Nack WA, Chen G (2016) Syntheses and transformations of α-amino acids via palladium-catalyzed auxiliary-directed sp3 C-H functionalization. Acc Chem Res 49:635–645

    CAS  PubMed  Google Scholar 

  • Honigberg LA, Smith AM, Sirisawad M, Verner E, Loury D, Chang B, Li S, Pan Z, Thamm DH, Miller RA, Buggy JJ (2010) The bruton tyrosine kinase inhibitor pci-32765 blocks B-cell activation and is efficacious in models of autoimmune disease and B-cell malignancy. Proc Natl Acad Sci USA 107:13075–13080

    CAS  PubMed  PubMed Central  Google Scholar 

  • Hu QW, Cai LW, Cao Y, Yu ZB (2014) Preparation method of 1-(3-(3-(4-chlorophenyl)propoxy)propyl)piperidine hydrochloride. CN 104447620A.

  • Hu Y, Chen J, Li B, Zhang Z, Gridnev ID, Zhang W (2020) Nickel-catalyzed asymmetric hydrogenation of 2-amidoacrylates. Angew Chem Int Ed 132:5409–5413

    Google Scholar 

  • Kastin A (2013) Handbook of biologically active peptides, 2nd edn. Academic Press, Cambridge

    Google Scholar 

  • Kawamura A, Moriwaki H, Röschenthaler GV, Kawada K, Aceña JL, Soloshonok VA (2015) Synthesis of (2S,3S)-β-(trifluoromethyl)-α, β-diamino acid by Mannich addition of glycine Schiff base Ni(II) complexes to N-tert-butylsulfinyl-3,3,3-trifluoroacetaldimine. J Fluorine Chem 171:67–72

    CAS  Google Scholar 

  • Kawashima A, Shu S, Takeda R, Kawamura A, Sato T, Moriwaki H, Wang J, Izawa K, Aceña JL, Soloshonok VA, Liu H (2016) Advanced asymmetric synthesis of (1R,2S)-1-amino-2-vinylcyclopropanecarboxylic acid by alkylation/cyclization of newly designed axially chiral Ni(II) complex of glycine Schiff base. Amino Acids 48:973–986

    CAS  PubMed  Google Scholar 

  • Keating GM (2015) Ledipasvir/Sofosbuvir: a review of its use in chronic hepatitis C. Drugs 75:675–685

    CAS  PubMed  Google Scholar 

  • Kim Y, Park J, Kim MJ (2011) Dynamic kinetic resolution of amines and amino acids by enzyme-metal cocatalysis. ChemCatChem 3:271–277

    CAS  Google Scholar 

  • Kirstein AS, Augustin A, Penke M, Cea M, Körner A, Kiess W, Garten A (2019) The novel phosphatidylinositol-3-kinase (PI3K) inhibitor alpelisib effectively inhibits growth of PTEN-haploinsufficient lipoma cells. Cancers 11:1586

    CAS  PubMed Central  Google Scholar 

  • Krogmann A, Peters L, von Hardenberg L, Bödeker K, Nöhles VB, Correll CU (2019) Keeping up with the therapeutic advances in schizophrenia: a review of novel and emerging pharmacological entities. CNS Spectr 24:38–69

    PubMed  Google Scholar 

  • Kukhar VP, Soloshonok VA (1994) Fluorine-Containing Amino Acids. Synthesis and Properties. John Wiley & Sons Ltd., Hoboken

    Google Scholar 

  • Kukhar VP, Sorochinsky AE, Soloshonok VA (2009) Practical synthesis of fluorine-containing α-and β-amino acids: recipes from Kiev, Ukraine. Future Med Chem 1:793–819

    CAS  PubMed  Google Scholar 

  • Kumar B, Kuhad A (2018) Lumateperone: a new treatment approach for neuropsychiatric disorders. Drugs Today 54:713–719

    CAS  Google Scholar 

  • Kuwano R, Okuda S, Ito Y (1998) Catalytic asymmetric synthesis of β-hydroxy-α-amino acids: highly enantioselective hydrogenation of β-Oxy-α-acetamidoacrylates. J Org Chem 63:3499–3503

    CAS  Google Scholar 

  • Lau JL, Dunn MK (2018) Therapeutic peptides: historical perspectives, current development trends, and future directions. Bioorg Med Chem 26:2700–2707

    CAS  PubMed  Google Scholar 

  • Li S, Yang J (2020) Pitolisant for treating patients with narcolepsy. Expert Rev Clin Pharmacol 13:79–84

    CAS  PubMed  Google Scholar 

  • Li P, Zhang Q, Robichaud AJ, Lee T, Tomesch J, Yao W, Deard JD, Snyder GL, Zhu H, Peng Y, Hendrick JP, Vanover KE, Davis RE, Mates S, Wennogle LP (2014) Discovery of a tetracyclic quinoxaline derivative as a potent and orally active multifunctional drug candidate for the treatment of neuropsychiatric and neurological disorders. J Med Chem 57:2670–2682

    CAS  PubMed  Google Scholar 

  • Lombardi BA, Menichincheri M, Orsini P, Panzeri A, Perrone E, Vanotti E, et al (2009) Substituted Indazole Derivatives Active as Kinase Inhibitors. WO2009013126

  • Mahindra A, Millard CJ, Black I, Archibald LJ, Schwabe JWR, Jamieson AG (2019) Synthesis of HDAC substrate peptidomimetic inhibitors using fmoc amino acids incorporating zinc-binding groups. Org Lett 21:3178–3182

    CAS  PubMed  PubMed Central  Google Scholar 

  • Malerich JP, Lam JS, Hart B, Fine RM, Klebansky B, Tanga MJ, D’Andrea A (2010) Diamino-1,2,4-triazole derivatives are selective inhibitors of TYK2 and JAK1 over JAK2 and JAK3. Bioorg Med Chem Lett 20:7454–7457

    CAS  PubMed  Google Scholar 

  • Markham A (2019a) Alpelisib: first global approval. Drugs 79:1249–1253

    CAS  PubMed  Google Scholar 

  • Markham A (2019b) Erdafitinib: first global approval. Drugs 79:1017–1021

    CAS  PubMed  Google Scholar 

  • Markham A (2019c) Solriamfetol: first global approval. Drugs 79:785–790

    CAS  PubMed  Google Scholar 

  • Markham A, Duggan S (2019) Darolutamide: first approval. Drugs 79:1813–1818

    CAS  PubMed  Google Scholar 

  • Matveyenko AV, Dry S, Cox HI, Moshtaghian A, Gurlo T, Galasso R, Butler AE, Butler PC (2009) Beneficial endocrine but adverse exocrine effects of sitagliptin in the human islet amyloid polypeptide transgenic rat model of Type 2 diabetes—interactions with metformin. Diabetes 58:1604–1615

    CAS  PubMed  PubMed Central  Google Scholar 

  • Mei H, Han J, Fustero S, Medio-Simon M, Sedgwick DM, Santi C, Ruzziconi R, Soloshonok VA (2019a) Fluorine-containing drugs approved by the FDA in 2018. Chem Eur J 25:11797–11819

    CAS  PubMed  Google Scholar 

  • Mei H, Hiramatsu T, Takeda R, Moriwaki H, Abe H, Han JL, Soloshonok VA (2019b) Expedient asymmetric synthesis of (S)-2-Amino-4,4,4-trifluorobutanoic acid via alkylation of chiral nucleophilic glycine equivalent. Org Process Res Dev 23:629–634

    CAS  Google Scholar 

  • Mei H, Han J, Takeda R, Sakamoto T, Miwa T, Minamitsuji Y, Moriwaki H, Abe H, Soloshonok VA (2019c) Practical method for preparation of (S)-2-Amino-5,5,5-trifluoropentanoic acid via dynamic kinetic resolution. ACS Omega 4:11844–11851

    CAS  PubMed  PubMed Central  Google Scholar 

  • Mei H, Yin Z, Miwa T, Moriwaki H, Abe H, Han J, Soloshonok VA (2019d) Convenient asymmetric synthesis of Fmoc-(S)-6,6,6-trifluoro-Norleucine. Symmetry 11:578

    CAS  Google Scholar 

  • Mei H, Han J, Klika KD, Izawa K, Sato T, Meanwell NA, Soloshonok VA (2020) Applications of fluorine-containing amino acids for drug design. Eur J Med Chem 186:111826

    CAS  PubMed  Google Scholar 

  • Melnykov KP, Volochnyuk DM, Ryabukhin SV, Rusanov EB, Grygorenko OO (2019) A conformationally restricted GABA analogue based on octahydro-1H-cyclopenta[b]pyridine scaffold. Amino Acids 51:255–261

    CAS  PubMed  Google Scholar 

  • Menichincheri M, Ardini E, Magnaghi P, Avanzi N, Banfi P, Bossi R et al (2016) Discovery of entrectinib: a new 3-aminoindazole as a potent anaplastic lymphoma kinase (ALK), c-ros oncogene 1 kinase (ROS1), and pan-tropomyosin receptor kinases (pan-TRKs) inhibitor. J Med Chem 59:3392–3408

    CAS  PubMed  Google Scholar 

  • Merkens K, Troyano FJA, Djossou J, Gómez-Suárez A (2020) Synthesis of unnatural α-amino acid derivatives via light-mediated radical decarboxylative processes. Adv Synth Catal. https://doi.org/10.1002/adsc.202000300

    Article  Google Scholar 

  • Metz AE, Kozlowski MC (2015) Recent advances in asymmetric catalytic methods for the formation of acyclic α, α-disubstituted α-amino acids. J Org Chem 80:1–7

    CAS  PubMed  Google Scholar 

  • Mikami K, Fustero S, Sánchez-Roselló M, Aceña JL, Soloshonok VA, Sorochinsky AE (2011) Synthesis of fluorine containing β-amino acids. Synthesis 2011:3045–3079

    Google Scholar 

  • Mita T, Sugawara M, Saito K, Sato Y (2014) Catalytic enantioselective silylation of N-sulfonylimines: asymmetric synthesis of α-amino acids from CO2 via stereospecific carboxylation of α-amino silanes. Org Lett 16:3028–3031

    CAS  PubMed  Google Scholar 

  • Mkrtchyan AF, Saghyan AS, Hayriyan LA, Sargsyan AS, Karapetyan AJ, Tovmasyan AS, Tsaturyan AH, Minasyan EV, Poghosyan AS, Paloyan AM, Panosyan HA, Sahakyan LY (2020) Asymmetric synthesis, biological activity and molecular docking studies of some unsaturated α-amino acids, derivatives of glycine, allylglycine and propargylglycine. J Mol Struct 1208:127850

    CAS  Google Scholar 

  • Moilanen AM, Riikonen R, Oksala R, Ravanti L, Aho E, Wohlfahrt G, Nykänen PS, Törmäkangas OP, Palvimo JJ, Kallio PJ (2015) Discovery of ODM-201, a new-generation androgen receptor inhibitor targeting resistance mechanisms to androgen signaling-directed prostate cancer therapies. Sci Rep 5:12007

    PubMed  PubMed Central  Google Scholar 

  • Molinaro C, Scott JP, Shevlin M, Wise C, Ménard A, Gibb A, Junker EM, Lieberman D (2015) Catalytic, asymmetric, and stereodivergent synthesis of non-symmetric β, β-diaryl-α-amino acids. J Am Chem Soc 137:999–1006

    CAS  PubMed  Google Scholar 

  • Moore E, Fraley ME, Bell IM, Burgey CS, White RB, Li CC, Regan CP, Danziger A (2020) Characterization of ubrogepant: a potent and selective antagonist of the human calcitonin gene-related peptide receptor. J Pharmacol Exp Ther 373:160–166

    CAS  Google Scholar 

  • Murray CW, Newell DR, Angibaud P (2019) A successful collaboration between academia, biotech and pharma led to discovery of erdafitinib, a selective FGFR inhibitor recently approved by the FDA. Med Chem Commun 10:1509–1511

    CAS  Google Scholar 

  • Nagato Y, Kiyokawa M, Ueki Y, Kikuchi J, Ohmatsu K, Terada M, Ooi T (2020) Non-enzymatic hybrid catalysis for stereoconversion of L-amino acid derivatives to D-isomers. Asian J Org Chem 9:561–565

    CAS  Google Scholar 

  • Nian Y, Wang J, Zhou S, Wang S, Moriwaki H, Kawashima A, Soloshonok VA, Liu H (2015) Recyclable ligands for the non-enzymatic dynamic kinetic resolution of challenging α-amino acids. Angew Chem Int Ed 54:12918–12922

    CAS  Google Scholar 

  • Nian Y, Wang J, Moriwaki H, Soloshonok VA, Liu H (2017) Analysis of crystallographic structures of Ni(ii) complexes of α-amino acid Schiff bases: elucidation of the substituent effect on stereochemical preferences. Dalton Tran 46:4191–4198

    CAS  Google Scholar 

  • O’Shea JJ, Gadina M (2019) Selective Janus kinase inhibitors come of age. Nat Rev Rheumatol 15:74–75

    PubMed  Google Scholar 

  • Paim CS, Nogueira DR, Mitjans M, Lopez DR, de Lapuente PJ, Steppe M, Schapoval EES, Vinardell MP (2013) Biological safety studies of gemifloxacin mesylate and related substances. Photochem Photobiol Sci 12:805–812

    CAS  PubMed  Google Scholar 

  • Pan ZY, Scheerens H, Li SJ, Schultz BE, Sprengeler PA, Burrill LC, Mendonca RV, Sweeney MD, Scott KCK, Grothaus PG, Jeffery DA, Spoerke JM, Honigberg LA, Young PR, Dalrymple SA, Palmer JT (2007) Discovery of selective irreversible inhibitors for Bruton’s tyrosine kinase. Chem Med Chem 2:58–61

    CAS  PubMed  Google Scholar 

  • Pan S, Gray NS, Gao W, Mi Y, Fan Y, Wang X, Tuntland T, Che J, Lefebvre S, Chen Y, Chu A, Hinterding K, Gardin A, End P, Heining P, Bruns C, Cooke NG, Nuesslein-Hildesheim B (2013) Discovery of BAF312 (siponimod), a potent and selective S1P receptor modulator. ACS Med Chem Lett 4:333–337

    CAS  PubMed  PubMed Central  Google Scholar 

  • Pan T, Xia C, Jiang H, Zhang Z, Zhu X, Yang Y (2017) Chemical synthesis of the ODM-201’s diastereomers through an efficient intramolecular 1,3-dipolar cycloaddition. Chem Pharm Bull 65:582–585

    CAS  Google Scholar 

  • Pangan AL, Teixeira HD, Mohamed MEF, Othman AA, Klünder B (2020) Processes for the preparation of (3S,4R)-3-ethyl-4-(3H-imidazo[1,2-α]pyrrolo[2,3-e]-pyrazin-8-yl)-N-(2,2,2-trifluoroethyl)pyrrolidine-1-carboxamide and solid state forms thereof. U.S. Patent 10550126

  • Parmentier JM, Voss J, Graff C, Schwartz A, Argiriadi M, Friedman M, Camp HS, Padley RJ, George JS, Hyland D, Rosebraugh M, Wishart N, Olson L, Long AJ (2018) In vitro and in vivo characterization of the JAK1 selectivity of upadacitinib (ABT-494). BMC Rheumatol 2:23

    PubMed  PubMed Central  Google Scholar 

  • Perera TPS, Jovcheva E, Mevellec L, Vialard J, De Lange D, Verhulst T, Paulussen C et al (2017) Discovery and pharmacological characterization of JNJ-42756493 (Erdafitinib), a functionally selective small-molecule FGFR family inhibitor. Mol Cancer Ther 16:1010–1020

    CAS  PubMed  Google Scholar 

  • Periasamy M, Gurubrahamam R, Sanjeevakumar N, Dalai M, Alakonda L, Reddy PO (2013) Convenient methods for the synthesis of chiral amino alcohols and amines. Chimia 67:23–29

    CAS  PubMed  Google Scholar 

  • Popkov A, De Spiegeleer B (2012) Chiral nickel (II) complexes in the preparation of 11C- and 18F-labelled enantiomerically pure α-amino acids. Dalton Trans 41:1430–1440

    CAS  PubMed  Google Scholar 

  • Robichaud AJ, Lee T, Deng W, Mitchell IS, Chen W, McClung CD (2003) Substituted heterocycle fused gamma-carbolines. U.S. Patent 6548493.

  • Romoff TT, Palmer AB, Mansour N, Creighton CJ, Miwa T, Ejima Y, Moriwaki H, Soloshonok VA (2017) Scale-up synthesis of (R)- and (S)-N-(2-Benzoyl-4-chlorophenyl)-1-(3,4-dichlorobenzyl)pyrrolidine-2-carboxamide hydrochloride, a versatile reagent for the preparation of tailor-made α- and β-amino acids in an enantiomerically pure form. Org Process Res Dev 21:732–739

    CAS  Google Scholar 

  • Romoff TT, Ignaci BG, Mansour N, Palmer AB, Creighton CJ, Abe H, Moriwaki H, Han JL, Konno H, Soloshonok VA (2020) Large-scale synthesis of the glycine schiff base Ni(II) complex derived from (S)- and (R)-N-(2-Benzoyl-4-chlorophenyl)-1-[(3,4-dichlorophenyl)methyl]-2-pyrrolidinecarboxamide. Org Process Res Dev 24:294–300

    CAS  Google Scholar 

  • Roskoski R Jr (2020) Properties of FDA-approved small molecule protein kinase inhibitors: a 2020 update. Pharmacol Res 152:104609

    CAS  PubMed  Google Scholar 

  • Sandanayaka VP, Shacham S, McCauley D, Shechter S (2013) Hydrazide containing nuclear transport modulators and uses thereof. WO2013019548

  • Sato T, Izawa K, Aceña JL, Liu H, Soloshonok VA (2016) Tailor-made α-amino acids in pharmaceutical industry: synthetic approaches to (1R,2S)-1-Amino-2-vinylcyclopropane-1-carboxylic Acid (Vinyl-ACCA). Eur J Org Chem 2016:2757–2774

    CAS  Google Scholar 

  • Saxty G, Murray CW, Berdini V, Besong GE, Hamlett CCF, Johnson CN, et al. (2011) Pyrazolyl Quinazoline kinase inhibitors. PCT Int Appl. WO2011135376

  • Schwartz JC (2011) The histamine H3 receptor: from discovery to clinical trials with pitolisant. Br J Pharmacol 163:713–721

    CAS  PubMed  PubMed Central  Google Scholar 

  • Schwartz JC, Garbarg M, Lecounte JM, Ligneau X, Schunacx WG, Stark H (2000) Non-imidazole alkyl amines as histamine H-3 receptor ligands and their therapeutic applications. P PCT Int Appl. WO2000006254

  • Schweitzer PK, Rosenberg R, Zammit GK, Gotfried M, Chen D, Carter LP, Wang H, Lu Y, Black J, Malhotra A, Strohl KP (2019) Solriamfetol for excessive sleepiness in obstructive sleep apnea (TONES 3). A randomized controlled trial. Am J Respir Crit Care Med 199:1421–1431

    CAS  PubMed  PubMed Central  Google Scholar 

  • Scott LJ (2020) Ubrogepant: first approval. Drugs 80:323–328

    PubMed  PubMed Central  Google Scholar 

  • Shahzad D, Saeed A, Larik FA, Channar PA, Abbas Q, Alajmi MF, Arshad I, Erben MF, Hassan M, Raza H, Seo SY, EI-Seedi HR (2019) Novel C-2 symmetric molecules as α-glucosidase and α-amylase inhibitors: design, synthesis, kinetic evaluation, molecular docking and pharmacokinetics. Molecules 24:1511

    CAS  PubMed Central  Google Scholar 

  • Shirahashi H, Toriihara E, Suenaga Y, Yoshida H, Akaogi K, Endou Y, Wakabayashi M, Takashima M (2019) The discovery of novel 3-aryl-indazole derivatives as peripherally restricted pan-Trk inhibitors for the treatment of pain. Bioorg Med Chem Lett 29:2320–2326

    CAS  PubMed  Google Scholar 

  • Shu L, Chen C, Huan X, Huang H, Wang M, Zhang J, Yan Y, Liu J, Zhang T, Zhang D (2020) Design, synthesis, and pharmacological evaluation of 4-or 6-phenyl-pyrimidine derivatives as novel and selective Janus kinase 3 inhibitors. Eur J Med Chem 191:112148

    PubMed  Google Scholar 

  • So SM, Kim H, Mui L, Chin J (2012) Mimicking nature to make unnatural amino acids and chiral diamines. Eur J Org Chem 2012:229–241

    CAS  Google Scholar 

  • Soloshonok VA (2002) Highly diastereoselective michael addition reactions between nucleophilic glycine equivalents and β-substituted-α, β-unsaturated carboxylic acid derivatives a general approach to the stereochemically defined and sterically χ-constrained α-amino acids. Curr Org Chem 6:341–364

    CAS  Google Scholar 

  • Soloshonok VA, Izawa K (2009) Asymmetric synthesis and application of α-Amino acids. In: Soloshonok VA, Izawa K (eds) ACS Symposium Series, vol 1009. Oxford University Press, Oxford

  • Soloshonok VA, Sorochinsky AE (2010) Practical methods for the synthesis of symmetrically α, α-disubstituted-α-amino acids. Synthesis 2010:2319–2344

    Google Scholar 

  • Soloshonok VA, Kukhar VP, Galushko SV, Svistunova NY, Avilov DV, Kuzmina NA, Raevski NI, Struchkov YT, Pysarevsky AP, Belokon YN (1993) General method for the synthesis of enantiomerically pure β-hydroxy-α-amino acids, containing fluorine atoms in the side chains. Case of stereochemical distinction between methyl and trifluoromethyl groups. X-ray crystal and molecular structure of the Nickel(II) complex of (2S,3S)-2-(Trifluoromethyl)threonine. J Chem Soc Perkin Trans 1:3143–3155

    Google Scholar 

  • Soloshonok VA, Avilov DV, Kukhar VP (1996) Highly diastereoselective asymmetric aldol reactions of chiral Ni(II)-complex of glycine with trifluoromethyl ketones. Tetrahedron Asymmetry 7:1547–1550

    CAS  Google Scholar 

  • Soloshonok VA, Avilov DV, Kukhar VP, Meervelt LV, Mischenko N (1997a) An efficient asymmetric synthesis of (2S,3S)-3-trifluoromethylpyroglutamic acid. Tetrahedron Lett 38:4903–4904

    CAS  Google Scholar 

  • Soloshonok VA, Avilov DV, Kukhar VP, Meervelt LV, Mischenko N (1997b) Highly diastereoselective aza-aldol reactions of a chiral Ni (II) complex of glycine with imines. An efficient asymmetric approach to 3-perfluoroalkyl-2, 3-diamino acids. Tetrahedron Lett 38:4671–4674

    CAS  Google Scholar 

  • Soloshonok VA, Cai C, Hruby VJ, Meervelt LV (1999a) Asymmetric synthesis of novel highly sterically constrained (2S,3S)-3-methyl-3-trifluoromethyl- and (2S,3S,4R)-3-trifluoromethyl-4-methylpyroglutamic acids. Tetrahedron 55:12045–12058

    CAS  Google Scholar 

  • Soloshonok VA, Cai C, Hruby VJ (1999b) Asymmetric michael addition reactions of chiral Ni(II) complex of glycine with N-(Enoyl)oxazolidinones: improved reactivity and stereochemical outcome. Tetrahedron Asymmetry 10:4265–4269

    CAS  Google Scholar 

  • Soloshonok VA, Cai C, Hruby VJ (2000a) A practical asymmetric synthesis of enantiomerically pure 3-substituted pyroglutamic acids and related compounds. Angew Chem Int Ed 39:2172–2175

    CAS  Google Scholar 

  • Soloshonok VA, Cai C, Hruby VJ (2000b) (S)- or (R)-N-(E-enoyl)-4-phenyl-1,3-oxazolidin-2-ones: ideal michael acceptors to afford a virtually complete control of simple and face diastereoselectivity in addition reactions with glycine derivatives. Org Lett 2:747–750

    CAS  PubMed  Google Scholar 

  • Soloshonok VA, Cai C, Hruby VJ (2000c) Toward design of a practical methodology for stereocontrolled synthesis of χ-constrained pyroglutamic acids and related compounds. Virtually complete control of simple diastereoselectivity in the michael addition reactions of glycine Ni(II) complexes with N-(Enoyl)oxazolidinones. Tetrahedron Lett 41:135–139

    CAS  Google Scholar 

  • Soloshonok VA, Tang X, Hruby VJ, Meervelt LV (2001a) Asymmetric synthesis of α,β-Dialkyl-α-Phenylalanines via direct alkylation of chiral alanine derivative with racemic α-Alkylbenzylbromides. A case of high enantiomer differentiation at room temperature. Org Lett 3:341–343

    CAS  PubMed  Google Scholar 

  • Soloshonok VA, Tang X, Hruby VJ (2001b) Large-scale asymmetric synthesis of novel sterically constrained 2’,6’-dimethyl- and α,2’,6’-trimethyltyrosine and –phenylalanine derivatives via alkylation of chiral equivalents of nucleophilic glycine and alanine. Tetrahedron 57:6375–6382

    CAS  Google Scholar 

  • Soloshonok VA, Ueki H, Ellis TK, Yamada T, Ohfune Y (2005) Application of modular nucleophilic glycine equivalents for truly practical asymmetric synthesis of β-substituted pyroglutamic acids. Tetrahedron Lett 46:1107–1110

    CAS  Google Scholar 

  • Soloshonok VA, Ellis TK, Ueki H, Ono T (2009) Resolution/deracemization of chiral α-amino acids using resolving reagents with flexible stereogenic centers. J Am Chem Soc 131:7208–7209

    CAS  PubMed  Google Scholar 

  • Soloshonok VA, Wzorek A, Klika KD (2017) A question of policy: should tests for the self-disproportionation of enantiomers (SDE) be mandatory for reports involving scalemates? Tetrahedron Asymmetry 28:1430–1434

    CAS  Google Scholar 

  • Sorochinsky AE, Soloshonok VA (2010) Asymmetric synthesis of fluorine-containing amines, amino alcohols, α- and β-amino acids mediated by chiral sulfinyl group. J Fluorine Chem 131:127–139

    CAS  Google Scholar 

  • Sorochinsky AE, Aceña JL, Moriwaki H, Sato T, Soloshonok VA (2013a) Asymmetric synthesis of α-amino acids via homologation of Ni(II) complexes of glycine Schiff bases; Part 1: alkyl halide alkylations. Amino Acids 45:691–718

    CAS  PubMed  Google Scholar 

  • Sorochinsky AE, Aceña JL, Moriwaki H, Sato T, Soloshonok VA (2013b) Asymmetric synthesis of α-amino acids via homologation of Ni(II) complexes of glycine Schiff bases. Part 2: Aldol, Mannich addition reactions, deracemization and (S) to (R) interconversion of α-amino acids. Amino Acids 45:1017–1033

    CAS  PubMed  Google Scholar 

  • Sorochinsky AE, Katagiri T, Ono T, Wzorek A, Aceña JL, Soloshonok VA (2013c) Optical purifications via self-disproportionation of enantiomers by achiral chromatography; case study of a series of α-CF3-containing secondary alcohols. Chirality 25:365–368

    CAS  PubMed  Google Scholar 

  • Sorochinsky AE, Aceña JL, Soloshonok VA (2013d) Self-Disproportionation of enantiomers of chiral, non-racemic fluoroorganic compounds: role of fluorine as enabling element. Synthesis 45:141–152

    CAS  Google Scholar 

  • Stork G, Leong AYW, Touzin AM (1976) Alkylation and Michael additions of glycine ethyl ester. Use in alpha.-amino acid synthesis and as acyl carbanion equivalent. J Org Chem 41:3491–3493

    CAS  PubMed  Google Scholar 

  • Stuyckens K, Perezruixo JJ, Deporre PMZ, Avadhani AN, Loriot Y, Siefker-Radtke AO (2018) Cancer treatment. PCT Int Appl. WO2018141921

  • Syed YY (2016) Pitolisant: first global approval. Drugs 76:1313–1318

    CAS  PubMed  Google Scholar 

  • Syed YY (2019) Selinexor: first global approval. Drugs 79:1485–1494

    PubMed  Google Scholar 

  • Syed YY (2020) Zanubrutinib: first approval. Drugs 80:91–97

    CAS  PubMed  Google Scholar 

  • Tageja N (2011) Lenalidomide—current understanding of mechanistic properties. Anti-Cancer Agents Med Chem 11:315–326

    CAS  Google Scholar 

  • Takeda R, Kawamura A, Kawashima A, Sato T, Moriwaki H, Izawa K, Akaji K, Wang S, Liu H, Aceña JL, Soloshonok VA (2014) Chemical dynamic kinetic resolution and (S)/(R)-interconversion of unprotected α-amino acids. Angew Chem Int Ed 53:12214–12217

    CAS  Google Scholar 

  • Tang X, Soloshonok VA, Hruby VJ (2000) Convenient asymmetric synthesis of enantiomerically pure 2',6'-dimethyltyrosine (DMT) via alkylation of chiral nucleophilic glycine equivalent. Tetrahedron Asymmetry 11:2917–2925

    CAS  Google Scholar 

  • Taylor SM, Yamada T, Ueki H, Soloshonok VA (2004) Asymmetric synthesis of enantiomerically pure 4-aminoglutamic acids via methylenedimerization of chiral glycine equivalents with dichloromethane under operationally convenient conditions. Tetrahedron Lett 45:9159–9162

    CAS  Google Scholar 

  • Taylor J, Coleman M, Alvarez K, Pichardo J, Sen F, Chung SS (2018) Selinexor, a first-in-class XPO1 inhibitor, is efficacious and tolerable in patients with myelodysplastic syndromes refractory to hypomethylating agents. Blood 132:233

    Google Scholar 

  • Tefferi A (2012) Compositions and methods for treating myelofibrosis. WO2012060847

  • Thorpy MJ (2020) Recently approved and upcoming treatments for narcolepsy. CNS Drugs 2020:1–19

    Google Scholar 

  • Törmäkangas O, Heikkinen T (2016) A carboxamide derivative and its diastereomers in stable crystalline form. PCT Int Appl. WO2016120530

  • Tyler PM, Servos MM, de Vries RC, Klebanov B, Kashyap T, Sacham S, Landesman Y, Dougan M, Dougan SK (2017) Clinical dosing regimen of selinexor maintains normal immune homeostasis and T-cell effector function in mice: implications for combination with immunotherapy. Mol Cancer Ther 16:428–439

    CAS  PubMed  PubMed Central  Google Scholar 

  • Vanover KE, Davis RE, Zhou Y, Ye W, Brašić JR, Gapasin L, Saillard J, Weingart M, Litman RE, Mates S, Wong DF (2019) Dopamine D 2 receptor occupancy of lumateperone (ITI-007): a positron emission tomography study in patients with schizophrenia. Neuropsychopharmacology 44:598–605

    CAS  PubMed  Google Scholar 

  • Vauquelin LN, Robiquet PJ (1806) The discovery of a new plant principle in Asparagus sativus. Ann Chim 57:88–93

    Google Scholar 

  • Verhoork SJM, Jennings CE, Rozatian N, Reeks J, Meng J, Corlett EK, Bunglawala F, Noble MEM, Leach AG, Coxon CR (2019) Tuning the binding affinity and selectivity of perfluoroaryl-stapled peptides by cysteine-editing. Chem Eur J 25:177–182

    CAS  PubMed  Google Scholar 

  • Vickery HB, Schmidt CLA (1931) The history of the discovery of the amino acids. Chem Rev 9(169–318):120

    Google Scholar 

  • Vogl DT, Dingli D, Cornell RF, Huff CA, Jagannath S, Bhutani D (2018) Selective inhibition of nuclear exportwith oral selinexor for treatment of relapsed or refractory multiple myeloma. J Clin Oncol 36:859–866

    CAS  PubMed  PubMed Central  Google Scholar 

  • Walter HS, Rule SA, Dyer MJS, Karlin L, Jones C, Cazin B, Quittet P, Shah N, Hutchinson CV, Honda H, Duffy K, Birkett J, Jamieson V, Courtenay-Luck N, Yoshizawa T, Sharpe J, Ohno T, Abe S, Nishimura A, Cartron G, Morschhauser F, Fegan C, Salles G (2016) A Phase I clinical trial of the selective BTK Inhibitor ONO/GS-4059 in relapsed and refractory mature B-cell malignancies. Blood 127:411–419

    CAS  PubMed  PubMed Central  Google Scholar 

  • Wang J, Zhang L, Jiang H, Chen K, Liu H (2011) Application of nickel (II) complexes to the efficient synthesis of α- or β-amino acids. Chimia 65:919–924

    CAS  PubMed  Google Scholar 

  • Wang X, Ding J, Meng LH (2015) PI3K isoform-selective inhibitors: next-generation targeted cancer therapies. Acta Pharmacol Sin 36:1170–1176

    PubMed  PubMed Central  Google Scholar 

  • Wang Y, Song X, Wang J, Moriwaki H, Soloshonok VA, Liu H (2017) Recent approaches for asymmetric synthesis of α-amino acids via homologation of Ni(II) complexes. Amino Acids 49:1487–1520

    CAS  PubMed  Google Scholar 

  • Watkins JC, Olverman HJ (1987) Agonists and antagonists for excitatory amino acid receptors. Trends Neurosci 10:265–272

    CAS  Google Scholar 

  • Watterson SH, Liu QJ, Beaudoin Bertrand M, Batt DG, Li L, Pattoli MA, Skala S, Cheng L, Obermeier MT, Moore R, Yang Z, Vickery R, Elzinga PA, Discenza L, D’Arienzo C, Gillooly KM, Taylor TL, Pulicicchio C, Zhang Y, Heimrich E, Mclntyre KW, Ruan Q, Westhouse RA, Catlett IM, Zheng N, Chaudhry C, Dai J, Galella MA, Tebben AJ, Pokross M, Li J, Zhao R, Smith D, Pampulla R, Allentoff A, Wallace MA, Mathur A, Salter-Cid L, Macor JE, Cater PH, Fura A, Burke JR, Tino JA (2019) Discovery of Branebrutinib (BMS-986195): a strategy for identifying a highly potent and selective covalent inhibitor providing rapid in vivo inactivation of Bruton’s Tyrosine Kinase (BTK). J Med Chem 62:3228–3250

    CAS  PubMed  Google Scholar 

  • Weiland T, Bodanszky M (1991) The world of peptides: a brief history of peptide chemistry. Springer Verlag, Berlin-Heidelberg

    Google Scholar 

  • Werning G, Kharas MG, Okabe R, Moore SA, Leeman DS, Cullen DE, Gozo M, McDowell EP, Levine RL, Doukas J, Mak CC, Noronha G, Martin M, Ko YD, Lee BH, Soll RM, Tefferi A, Hood JD, Gilliland DG (2008) Efficacy of TG101348, a selective jak2 inhibitor, in treatment of a murine model of JAK2V617F-induced polycythemia vera. Cancer Cell 13:311–320

    Google Scholar 

  • Wishart N, Frank KE, Friedman M, George DM, Stewart KD, Wallace GA (2013) Tricyclic compounds. U.S. Patent 8426411

  • Xiang B, Belyk KM, Reamer RA, Yasuda N (2014) Discovery and application of doubly quaternized cinchona-alkaloid-based phase-transfer catalysts. Angew Chem Int Ed 53:8375–8378

    CAS  Google Scholar 

  • Yamada SI, Oguri T, Shioiri T (1976) Asymmetric synthesis of α-amino-acid derivatives by alkylation of a chiral Schiff base. J Chem Soc Chem Commun 1976:136–137

    Google Scholar 

  • Yamada T, Okada T, Sakaguchi K, Ohfune Y, Ueki H, Soloshonok VA (2006) Efficient asymmetric synthesis of novel 4-substituted and configurationally stable analogs of thalidomide. Org Lett 8:5625–5628

    CAS  PubMed  Google Scholar 

  • Yang J, Gao J (2019) Solriamfetol for the treatment of excessive daytime sleepiness associated with narcolepsy. Expert Rev Clin Pharmacol 12:723–728

    CAS  PubMed  Google Scholar 

  • Yasuda N, Cleator E, Kosjek B, Yin J, Xiang B, Chen F, Kuo SC, Belyk K, Mullens PR, Goodyear A, Edwards JS, Bishop B, Ceglia S, Belardi J, Tan L, Song ZJ, DiMichele L, Reamer R, Cabirol FL, Tang WL, Liu G (2017) Practical asymmetric synthesis of a calcitonin gene-related peptide (CGRP) receptor antagonist ubrogepant. Org Process Res Dev 21:1851–1858

    CAS  Google Scholar 

  • Yin Z, Moriwaki H, Abe H, Miwa T, Han JL, Soloshonok VA (2019) Large-scale asymmetric synthesis of Fmoc-(S)-2-amino-6,6,6-trifluorohexanoic acid. ChemistryOpen 8:701–704

    CAS  PubMed  PubMed Central  Google Scholar 

  • Yu J, Zhou P, Hu M, Yang L, Yan G, Xu R, Deng Y, Li X, Chen Y (2019) Discovery and biological evaluation of darolutamide derivatives as inhibitors and down-regulators of wild-type AR and the mutants. Eur J Med Chem 182:111608

    CAS  PubMed  Google Scholar 

  • Zhang Y, Li JK, Zhang FG, Ma JA (2020) Catalytic Asymmetric access to noncanonical chiral α-amino acids from cyclic iminoglyoxylates and enamides. J Org Chem 85:5580–5589

    CAS  PubMed  Google Scholar 

  • Zhou S, Wang J, Chen X, Aceña JL, Soloshonok VA, Liu H (2014) Chemical kinetic resolution of unprotected β-substituted-β-amino acids using recyclable chiral ligands. Angew Chem Int Ed 53:7883–7886

    CAS  Google Scholar 

  • Zhu Y, Han JL, Wang J, Shibata N, Sodeoka M, Soloshonok VA (2018) Modern approaches for asymmetric construction of carbon−fluorine quaternary stereogenic centers: synthetic challenges and pharmaceutical needs. Chem Rev 118:3887–3964

    CAS  PubMed  PubMed Central  Google Scholar 

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Acknowledgements

We gratefully acknowledge the financial support from the National Natural Science Foundation of China (No. 21761132021), the Qing-Lan Project of Jiangsu Province (for Han), and IKERBASQUE, Basque Foundation for Science (for Soloshonok).

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Authors and Affiliations

  1. Jiangsu Co-Innovation Center of Efficient Processing and Utilization of Forest Resources, College of Chemical Engineering, Nanjing Forestry University, Nanjing, 210037, China

    Zizhen Yin & Jianlin Han

  2. Department of Chemistry, University of Massachusetts Boston, 100 Morrissey Boulevard, Boston, MA, 02125, USA

    Wenfei Hu & Wei Zhang

  3. Department of Biological Engineering, Graduate School of Science and Engineering, Yamagata University, Yonezawa, Yamagata, 992-8510, Japan

    Hiroyuki Konno

  4. Hamari Chemicals Ltd, 1-4-29 Kunijima, Higashi-Yodogawa-ku, Osaka, 533-0024, Japan

    Hiroki Moriwaki & Kunisuke Izawa

  5. Department of Organic Chemistry I, Faculty of Chemistry, University of the Basque Country UPV/EHU, Paseo Manuel Lardizábal 3, 20018, San Sebastián, Spain

    Vadim A. Soloshonok

  6. Basque Foundation for Science, IKERBASQUE, Alameda Urquijo 36-5, Plaza Bizkaia, 48011, Bilbao, Spain

    Vadim A. Soloshonok

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  1. Zizhen Yin
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  8. Vadim A. Soloshonok
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Yin, Z., Hu, W., Zhang, W. et al. Tailor-made amino acid-derived pharmaceuticals approved by the FDA in 2019. Amino Acids 52, 1227–1261 (2020). https://doi.org/10.1007/s00726-020-02887-4

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