Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml
Synthesis 2021; 53(03): 391-417
DOI: 10.1055/s-0040-1707314
DOI: 10.1055/s-0040-1707314
review
Synthesis of Azido Acids and Their Application in the Preparation of Complex Peptides
This work was supported by a Natural Sciences and Engineering Research Council of Canada (NSERC) Discovery Grant to S.D.T. (04233-2017). R.M. is grateful to NSERC for a postgraduate scholarship. M.N. is grateful to the Ontario Government for a postgraduate scholarship.
Abstract
Azido acids are important synthons for the synthesis of complex peptides. As a protecting group, the azide moiety is atom-efficient, easy to install and can be reduced in the presence of many other protecting groups, making it ideal for the synthesis of branched and/or cyclic peptides. α-Azido acids are less bulky than urethane-protected counterparts and react more effectively in coupling reactions of difficult-to-form peptide and ester bonds. Azido acids can also be used to form azoles on complex intermediates. This review covers the synthesis of azido acids and their application to the total synthesis of complex peptide natural products.
1 Introduction
2 Synthesis of α-Azido Acids
2.1 From α-Amino Acids or Esters
2.2 Via α-Substitution
2.3 Via Electrophilic Azidation
2.4 Via Condensation of N-2-Azidoacetyl-4-Phenylthiazolidin- 2-Thi one Enolates with Aldehydes and Acetals
2.5 Synthesis of α,β-Unsaturated α-Azido Acids and Esters
3 Synthesis of β-Azido Acids
3.1 Preparation of Azidoalanine and 3-Azido-2-aminobutanoic Acids
3.2 General Approaches to Preparing β-Azido Acids Other Than Azi doalanine and AABA
4 Azido Acids in Total Synthesis
4.1 α-Azido Acids
4.2 β-Azido Acids and Azido Acids Containing an Azide on the Side Chain
5 Conclusions
Publication History
Received: 23 July 2020
Accepted after revision: 06 September 2020
Article published online:
09 November 2020
© 2020. Thieme. All rights reserved
Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany
-
References
- 1 Zaloom J, Roberts DC. J. Org. Chem. 1981; 46: 5173
- 2 Alper PB, Hung S.-C, Wong C.-H. Tetrahedron Lett. 1996; 37: 6029
- 3 Nyffeler PT, Liang CH, Koeller KM, Wong CH. J. Am. Chem. Soc. 2002; 124: 10773
- 4 Goddard-Borger ED, Stick RV. Org. Lett. 2007; 9: 3797
- 5 Goddard-Borger ED, Stick RV. Org. Lett. 2011; 13: 2514
- 6 Suárez JR, Trastoy B, Pérez-Ojeda ME, Marín-Barrios R, Chiara JL. Adv. Synth. Catal. 2010; 352: 2515
- 7 Ye H, Liu R, Li D, Liu Y, Yuan H, Guo W, Zhou L, Cao X, Tian H, Shen J, Wang PG. Org. Lett. 2013; 15: 18
- 8 Potter GT, Jayson GC, Miller GJ, Gardiner JM. J. Org. Chem. 2016; 81: 3443
-
9
Meng G,
Taijie Guo,
Ma T,
Zhang J,
Shen Y,
Sharpless KB,
Dong J.
Nature 2019; 574: 86
- 10 Rijkers DT. S, van Vugt HH. R, Jacobs HJ. F, Liskamp RM. J. Tetrahedron Lett. 2002; 43: 3657
- 11 Hoffman RV, Kim H. Tetrahedron 1992; 48: 3007
- 12 Green JE, Bender DM, Jackson S, O’Donnell MJ, McCarthy JR. Org. Lett. 2009; 11: 807
- 13 Curtius T, Darapsky A, Bockmühl A. Ber. Dtsch. Chem. Ges. 1908; 41: 344
- 14 Forster MO, Fierz HE. J. Chem. Soc., Trans. 1908; 93: 1859
- 15 Cheng B, Müller R, Trauner D. Angew. Chem. Int. Ed. 2017; 56: 12755
- 16 Breuning A, Vicik R, Schirmeister T. Tetrahedron: Asymmetry 2003; 14: 3301
- 17 Legters J, Thijs L, Zwanenberg B. Tetrahedron 1991; 41: 5287
- 18 Hüttel S, Testolin G, Herrmann J, Planke T, Gille F, Moreno M, Stadler M, Brönstrup M, Kirschning A, Müller R. Angew. Chem. Int. Ed. 2017; 56: 12760
- 19 Planke T, Moreno M, Hüttel S, Fohrer J, Gille F, Norris MD, Siebke M, Wang L, Müller R, Kirschning A. Org. Lett. 2019; 21: 1359
- 20 Moeller M, Norris MD, Planke T, Cirnski K, Herrmann J, Müller R, Kirschning A. Org. Lett. 2019; 21: 8369
- 21 Gao Y, Sharpless KB. J. Am. Chem. Soc. 1988; 110: 7538
- 22 Pandey SK, Kumar P. Tetrahedron Lett. 2006; 47: 4167
- 23 Messik F, Oberthür M. Angew. Chem. Int. Ed. 2013; 52: 5871
- 24 Lin C.-K, Yun W.-Y, Lin L.-T, Cheng W.-C. Org. Biomol. Chem. 2016; 14: 4054
- 25 Kang S, Rho H, Yoon S, Shin J, Campus NS. J. Chem. Soc., Perkin Trans. 1 1994; 3513
- 26 Fleming PR, Sharpless KB. J. Org. Chem. 1991; 56: 2869
- 27 Ko SY. J. Org. Chem. 2002; 67: 2689
- 28 Boger DL, Patane MA, Zhou J. J. Am. Chem. Soc. 1994; 116: 8544
- 29 Olivier KS, Van Nieuwenhze MS. Org. Lett. 2010; 12: 1680
- 30 Heravi MM, Zadsirjan V, Farajpour B. RSC Adv. 2016; 6: 30498
- 31 Evans DA, Ellman JA, Dorow RL. Tetrahedron Lett. 1987; 28: 1123
- 32 Gustafsson T, Saxin M, Kihlberg J. J. Org. Chem. 2002; 68: 2506
- 33a Pettit GR, Smith TH, Arce PM, Flahive EJ, Anderson CR, Chapuis J.-C, Xu J. P, Groy TL, Belcher PE, Macdonald CB. J. Nat. Prod. 2015; 78: 476
- 33b Evans DA, Sjogren EB, Weber AE, Conn RE. Tetrahedron Lett. 1987; 28: 39
- 34 Evans DA, Weber AE. J. Am. Chem. Soc. 1987; 109: 7151
- 35 Brown HC, Midland MM, Levy AB. J. Am. Chem. Soc. 1972; 94: 2114
- 36 Owa T, Otsuka M, Ohno M. Chem. Lett. 1988; 1873
- 37 Boger DL, Menezes RF. J. Org. Chem. 1992; 57: 4331
- 38 Evans DA, Britton TC, Ellman JA, Dorow RL. J. Am. Chem. Soc. 1990; 112: 4011
- 39 Evans DA, Britton TC. J. Am. Chem. Soc. 1987; 109: 6881
- 40 Ager DJ, Prakash I, Schaad DR. Chem. Rev. 1996; 96: 835
- 41 Beylin VG, Chen HG, Dunbar CJ, Goel OP, Harter W, Marlett M, Topliss JG. Tetrahedron Lett. 1993; 34: 953
- 42 Beylin VG, Marlatt M, Leja B, Goel OP. Tetrahedron Lett. 1992; 33: 3293
- 43 Evans DA, Lundy KM. J. Am. Chem. Soc. 1992; 114: 1495
- 44 Burke TR, Liu D.-G, Gao Y. J. Org. Chem. 2000; 65: 6288
- 45 Dharanipragada R, Nicolas E, Toth G, Hruby VJ. Tetrahedron Lett. 1989; 30: 6841
- 46 Shaw AN, Dolle RE, Kruse LI. Tetrahedron Lett. 1990; 31: 5081
- 47 Ahn KH, Kim SK, Ham C. Tetrahedron Lett. 1998; 39: 6321
- 48 Hanessian S, Wang W, Gai Y. Tetrahedron Lett. 1996; 37: 7477
- 49 Manpadi M, Kireev AS, Magedov IV, Altig J, Tongwa P, Antipin MY, Evidente A, Van Otterlo WA. L, Kornienko A. J. Org. Chem. 2009; 74: 7122
- 50 Hanessian S, Sancéau JY. Can. J. Chem. 1996; 74: 621
- 51 Reimer C, Bayer T, Schmitt H, Kessler H. J. Pept. Res. 2004; 63: 196
- 52 Liyanage W, Weerasinghe L, Strong RK, Del Valle JR. J. Org. Chem. 2008; 73: 7420
- 53 Patonay T, Hoffman RV. J. Org. Chem. 1995; 60: 2368
- 54 Patel J, Clavé G, Renard P.-Y, Franck X. Angew. Chem. Int. Ed. 2008; 47: 4224
- 55 Fernández-Valparis J, Romea P, Urpí F, Font-Bardia M. Org. Lett. 2017; 19: 64007
- 56 Fernández-Valparis J, Romea P, Urpí F. Eur. J. Org. Chem. 2019; 2745
- 57 Kakimoto M, Kai M, Kondo K. Chem. Lett. 1982; 11: 525
- 58 Henn L, Hickey DM. B, Moody CJ, Rees CW. J. Chem. Soc., Perkin Trans. 1 1984; 2189
- 59 Yamashita T, Kuranaga T, Inoue M. Org. Lett. 2015; 17: 2170
- 60 Mangold JB, Lavelle JM. Chem.-Biol. Interact. 1986; 60: 183
- 61 Roth S, Thomas NR. Synlett 2010; 607
- 62 Lau YH, Spring DR. Synlett 2011; 1917
- 63 Owais WM, Ronald RC, Kleinhofs A, Nilan RA. Mutat. Res. Lett. 1986; 175: 121
- 64 Arnold LD, May RG, Vederas JC. J. Am. Chem. Soc. 1988; 110: 2237
- 65 Arnold LD, Kalantar TH, Vederas JC. J. Am. Chem. Soc. 1985; 107: 7105
- 66 Wei L, Lubell WD. Can. J. Chem. 2001; 79: 94
- 67 Davoli P, Forni A, Moretti I, Prati F. Tetrahedron: Asymmetry 1995; 6: 2011
- 68 Luo Y, Blaskovich MA, Lajoie GA. J. Org. Chem. 1999; 64: 6106
- 69 Blaskovich MA, Evindar G, Rose NG. W, Wilkinson S, Luo Y, Lajoie GA. J. Org. Chem. 1998; 63: 3631
- 70 Panda G, Rao NV. Synlett 2004; 714
- 71 Miller N, Williams GM, Brimble MA. Org. Lett. 2009; 11: 2409
- 72 Pícha J, Buděšínský M, Macháčková K, Collinsová M, Jiráček J. J. Pept. Sci. 2017; 23: 202
- 73 Sharma K, Strizhak AV, Fowler E, Wang X, Xu W, Hatt Jensen C, Wu Y, Sore HF, Lau YH, Hyvönen M, Itzhaki LS, Spring DR. Org. Biomol. Chem. 2019; 17: 8014
- 74 Vreja IC, Kabatas S, Saka SK, Kröhnert K, Höschen C, Opazo F, Diederichsen U, Rizzoli SO. Angew. Chem. Int. Ed. 2015; 54: 5784
- 75 Schmidt U, Mundinger K, Riedl B, Haas G, Lau R. Synthesis 1992; 1201
- 76 Pearson C, Rinehart KL, Sugano M. Tetrahedron Lett. 1999; 40: 411
- 77 Piizzi G, Parker DT, Peng Y, Dobler M, Patnaik A, Wattanasin S, Liu E, Lenoir F, Nunez J, Kerrigan J, McKenney D, Osborne C, Yu D, Lanieri L, Bojkovic J, Dzink-Fox J, Lilly MD, Sprague ER, Lu Y, Wang H, Ranjitkar S, Xie L, Wang B, Glick M, Hamann LG, Tommasi R, Yang X, Dean CR. J. Med. Chem. 2017; 60: 5002
- 78 Sun D, Jones V, Carson EI, Lee RE. B, Scherman MS, McNeil MR, Lee RE. Bioorg. Med. Chem. Lett. 2007; 17: 6899
- 79 Nakamura Y, Hirai M, Tamotsu K, Yonezawa Y, Shin C. Bull. Chem. Soc. Jpn. 1995; 68: 1369
- 80 Nakamura Y, Shin C. Chem. Lett. 1992; 49
- 81 Xie W, Ding D, Zi W, Li G, Ma D. Angew. Chem. Int. Ed. 2008; 47: 2844
- 82 Zhou H, Van Der Donk WA. Org. Lett. 2002; 4: 1335
- 83 Nakajima K, Takai F, Tanaka T, Okawa K. Bull. Chem. Soc. Jpn. 1978; 51: 1577
- 84 Martin MJ, Rodriguez-Acebes R, Garcia-Ramos Y, Martinez V, Murcia C, Digon I, Marco I, Pelay-Gimeno M, Fernández R, Reyes F, Francesch AM, Munt S, Tulla-Puche J, Albericio F, Cuevas C. J. Am. Chem. Soc. 2014; 136: 6754
- 85 Sudhir VS, Kumar NY. P, Baig RB. N, Chandrasekaran S. J. Org. Chem. 2009; 74: 7588
- 86 Moreira R, Barnawi G, Beriashvili D, Palmer M, Taylor SD. Bioorg. Med. Chem. 2019; 27: 240
- 87 Sai Sudhir V, Phani Kumar NY, Chandrasekaran S. Tetrahedron 2010; 66: 1327
- 88 Baig RB. N, Varma RS. Chem. Commun. 2012; 48: 5853
- 89 Donnell AF, Kester R, Lou Y, Anthony J, Remiszewski S. US9422331B2, 2015
- 90 Dianati V, Shamloo A, Kwiatkowska A, Desjardins R, Soldera A, Day R, Dory YL. ChemMedChem 2017; 12: 1169
- 91 Han H, Yoon J, Janda KD. J. Org. Chem. 1998; 63: 2045
- 92 Chong JM, Sharpless KB. J. Org. Chem. 1985; 50: 1560
- 93 Choukroun R, Gervais D. J. Chem. Soc., Dalton Trans. 1980; 1800
- 94 Caron M, Carlier PR, Sharpless KB. J. Org. Chem. 1988; 53: 5185
- 95 Fringuelli F, Pizzo F, Vaccaro L. Synlett 2000; 311
- 96 Fringuelli F, Pizzo F, Vaccaro L. Tetrahedron Lett. 2001; 42: 1131
- 97 Fringuelli F, Pizzo F, Vaccaro L. J. Org. Chem. 2001; 66: 3554
- 98 Fringuelli F, Pizzo F, Vaccaro L. J. Org. Chem. 2001; 66: 4719
- 99 Fringuelli F, Pizzo F, Rucci M, Vaccaro L. J. Org. Chem. 2003; 68: 7041
- 100 Bunnage ME, Chernega AN, Davies SG, Goodwin CJ. J. Chem. Soc., Perkin Trans. 1 1994; 2373
- 101 Davies SG, Fletcher AM, Frost AB, Roberts PM, Thomson JE. Org. Lett. 2015; 17: 2254
- 102 Myers JK, Jacobsen EN. J. Am. Chem. Soc. 1999; 121: 8959
- 103 Taylor MS, Zalatan DN, Lerchner AM, Jacobsen EN. J. Am. Chem. Soc. 2005; 127: 1313
- 104 Horstmann TE, Guerin DJ, Miller SJ. Angew. Chem. 2000; 39: 3635
- 105 Guerin DJ, Miller SJ. J. Am. Chem. Soc. 2002; 124: 2134
- 106 Shyam PK, Jang H.-Y. Eur. J. Org. Chem. 2014; 1817
- 107 Zhou P, Lin L, Chen L, Zhong X, Liu X, Feng X. J. Am. Chem. Soc. 2017; 139: 13414
- 108 Zhou P, Liu X, Wu W, Xu C, Feng X. Org. Lett. 2019; 21: 1170
- 109 Su J, Qiu G, Liang S, Hu X. Synth. Commun. 2005; 35: 1427
- 110 Mangelinckx S, De Kimpe N. Synlett 2006; 369
- 111 Gu P, Su Y, Wu XP, Sun J, Liu W, Xue P, Li R. Org. Lett. 2012; 14: 2246
- 112 Evans DA, Ellman JA. J. Am. Chem. Soc. 1989; 111: 1063
- 113 Cramer N, Laschat S, Baro A, Schwalbe H, Richter C. Angew. Chem. Int. Ed. 2005; 44: 820
- 114 Marcelo F, Jiménez-Barbero J, Marrot J, Rauter AP, Sinaÿ P, Blériot Y. Chem. Eur. J. 2008; 14: 10066
- 115 Marcelo F, Abou-Jneid R, Sollogoub M, Marrot J, Rauter A, Blériot Y. Synlett 2009; 1269
- 116 Feng Y, Chen G. Angew. Chem. Int. Ed. 2010; 49: 958
- 117 Li L, Hu W, Jia Y. Tetrahedron 2014; 70: 7753
- 118 Guo Y, Zhou J, Gao B, Zhao M, Yan J.-L, Xu Z, Choi S, Ye T. Org. Lett. 2019; 21: 5471
- 119 Thijs L, Porskamp JJ. M, van Loon AA. W. M, Derks MP. W, Feenstra RW, Legters J, Zwanenburg B. Tetrahedron 1990; 46: 2611
- 120 Liao L, Zhou J, Xu Z, Ye T. Angew. Chem. Int. Ed. 2016; 55: 13263
- 121 Myers EL, Raines RT. Angew. Chem. Int. Ed. 2009; 48: 2359
- 122 Ghosh SK, Somanadhan B, Tan KS.-W, Butler MS, Lear MJ. Org. Lett. 2012; 14: 1560
- 123 Wu X, Park PK, Danishefsky SJ. J. Am. Chem. Soc. 2011; 133: 7700
- 124 Meldal M, Juliano MA, Jansson AM. Tetrahedron Lett. 1997; 38: 2531
- 125 Tornøe CW, Davis P, Porreca F, Meldal M. J. Pept. Sci. 2000; 6: 594
- 126 Pelletier JC, Lundquist JT. Org. Lett. 2001; 3: 781
- 127 Lundquist JT, Pelletier JC. Org. Lett. 2002; 4: 3219
- 128 Ghalit N, Rijkers DT. S, Kemmink J, Versluis C, Liskamp RM. J. Chem. Commun. 2005; 192
- 129 Lam HY, Zhang Y, Liu H, Xu J, Wong CT. T, Xu C, Li X. J. Am. Chem. Soc. 2013; 135: 6272
- 130 Lohani CR, Taylor R, Palmer M, Taylor SD. Org. Lett. 2015; 17: 748
- 131 Lohani CR, Taylor R, Palmer M, Taylor SD. Bioorg. Med. Chem. Lett. 2015; 25: 5490
- 132 Lohani CR, Rasera B, Scott B, Palmer M, Taylor SD. J. Org. Chem. 2016; 81: 2624
- 133 Lohani CR, Soley J, Kralt B, Palmer M, Taylor SD. J. Org. Chem. 2016; 81: 11831
- 134 Kralt B, Moreira R, Palmer M, Taylor SD. J. Org. Chem. 2020; 85: 2213
- 135 Chow HY, Chen D, Li X. Org. Biomol. Chem. 2020; 18: 4401
- 136 Zaloom J, Calandra M, Roberts DC. J. Org. Chem. 1985; 50: 2601
- 137 Nepomniaschiy N, Grimminger V, Cohen A, Digiovanni S, Lashuel HA, Brik A. Org. Lett. 2008; 10: 5243
- 138 Hojo H, Katayama H, Tano C, Nakahara Y, Yoneshige A. Tetrahedron Lett. 2011; 52: 635
- 139 Saxon E, Bertozzi CR. Science 2000; 287: 2007
- 140 Nilsson BL, Kiessling LL, Raines RT. Org. Lett. 2000; 2: 1939
- 141 Kleineweischede R, Hackenberger CP. R. Angew. Chem. Int. Ed. 2008; 47: 5984
- 142 Bogart JW, Bowers AA. Org. Biomol. Chem. 2019; 17: 3653
- 143 Just-Baringo X, Bruno P, Ottesen LK, Cañedo LM, Albericio F, Álvarez M. Angew. Chem. Int. Ed. 2013; 52: 7818
- 144 Lukszo J, Patterson D, Albericio F, Kates SA. Lett. Pept. Sci. 1996; 3: 157
- 145 Yamashita T, Matoba H, Kuranaga T, Inoue M. Tetrahedron 2014; 70: 7746
- 146 Itoh H, Miura K, Kamiya K, Yamashita T, Inoue M. Angew. Chem. Int. Ed. 2020; 59: 4564
- 147 Saxon E, Armstrong JI, Bertozzi CR. Org. Lett. 2000; 2: 2141
- 148 Brossmer R, Mack H. Tetrahedron Lett. 1981; 22: 933
- 149 Gololobov YG, Gusar’ NI, Chaus MP. Tetrahedron 1985; 41: 793
- 150 Chen J, Forsyth CJ. Org. Lett. 2003; 5: 1281
- 151 Chen J, Forsyth CJ. J. Am. Chem. Soc. 2003; 125: 8734
- 152 Chen J, Forsyth CJ. Proc. Natl. Acad. Sci. U.S.A. 2004; 101: 12067
- 153 Wang B, Forsyth CJ. Synthesis 2009; 3: 2873
- 154 Wang B, Huang PH, Chen CS, Forsyth CJ. J. Org. Chem. 2011; 76: 1140
- 155 Nicolaou KC, Kim DW, Schlawe D, Lizos DE, de Noronha RG, Longbottom DA. Angew. Chem. Int. Ed. 2005; 44: 4925
- 156 Nicolaou KC, Lizos DE, Kim DW, Schlawe D, de Noronha RG, Longbottom DA, Rodriquez M, Bucci M, Cirino G. J. Am. Chem. Soc. 2006; 128: 4460
- 157 Nicolaou KC, Schlawe D, Kim DW, Longbottom DA, de Noronha RG, Lizos DE, Manam RR, Faulkner DJ. Chem. Eur. J. 2005; 11: 6197
- 158 Riedrich M, Harkal S, Arndt H. Angew. Chem. Int. Ed. 2007; 46: 2701
- 159 Loos P, Ronco C, Riedrich M, Arndt H. Eur. J. Org. Chem. 2013; 3290
- 160 Lu J, Riedrich M, Mikyna M, Arndt H. Angew. Chem. Int. Ed. 2009; 48: 8137
- 161 Wojtas KP, Riedrich M, Lu J.-Y, Winter P, Winkler T, Walter S, Arndt H.-D. Angew. Chem. Int. Ed. 2016; 55: 9772
- 162 Schwenk S, Ronco C, Oberheide A, Arndt HD. Eur. J. Org. Chem. 2016; 4795
- 163 Liu Y, Sun X, Zhang X, Liu J, Du Y. Org. Biomol. Chem. 2014; 12: 8453
- 164 Sun X, Liu Y, Liu J, Gu G, Du Y. Org. Biomol. Chem. 2015; 13: 4271
- 165 Liu Y, He P, Zhang Y, Zhang X, Liu J, Du Y. J. Org. Chem. 2018; 83: 3897
- 166 Liu Y, Ma Z, Zhao X, Shan Q, He P, Du Y, Wang Y. ChemistrySelect 2019; 4: 742
- 167 Isidro-Llobet A, Álvarez M, Albericio F. Chem. Rev. 2009; 109: 2455
- 168 Schmidt U, Mundinger K, Mangold R, Lieberknecht A. J. Chem. Soc., Chem. Commun. 1990; 1216
- 169 Schmidt U, Riedl B. J. Chem. Soc., Chem. Commun. 1992; 1186
- 170 Izzo I, Acosta GA, Tulla-Puche J, Cupido T, Martin-Lopez MJ, Cuevas C, Albericio F. Eur. J. Org. Chem. 2010; 2536
- 171 Kralt B, Moreira R, Palmer M, Taylor SD. J. Org. Chem. 2019; 84: 12021
- 172 Noden M, Moreira R, Huang E, Yousef A, Palmer M, Taylor SD. J. Org. Chem. 2019; 84: 5339
- 173 White CJ, Yudin AK. Org. Lett. 2012; 14: 2898
- 174 White CJ, Hickey JL, Scully CC. G, Yudin AK. J. Am. Chem. Soc. 2014; 136: 3728
- 175 Lecinska P, Corres N, Moreno D, García-Valverde M, Marcaccini S, Torroba T. Tetrahedron 2010; 66: 6783
- 176 Gao X, Ren Q, Choi S, Xu Z, Ye T. Front. Chem. 2015; 3: 1