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Epimerization-free access to C-terminal cysteine peptide acids, carboxamides, secondary amides, and esters via complimentary strategies
Chemical Science ( IF 8.4 ) Pub Date : 2017-11-09 00:00:00 , DOI: 10.1039/c7sc03553e
Christine A. Arbour 1, 2, 3, 4 , Thilini D. Kondasinghe 1, 2, 3, 4 , Hasina Y. Saraha 1, 2, 3, 4 , Teanna L. Vorlicek 1, 2, 3, 4 , Jennifer L. Stockdill 1, 2, 3, 4
Affiliation  

C-Terminal cysteine peptide acids are difficult to access without epimerization of the cysteine α-stereocenter. Diversification of the C-terminus after solid-phase peptide synthesis poses an even greater challenge because of the proclivity of the cysteine α-stereocenter to undergo deprotonation upon activation of the C-terminal carboxylic acid. We present herein two general strategies to access C-terminal cysteine peptide derivatives without detectable epimerization, diketopiperazine formation, or piperidinylalanine side products.

中文翻译:

通过互补策略免于差向异构化获得C端半胱氨酸肽酸,羧酰胺,仲酰胺和酯

如果没有半胱氨酸α-立体中心的差向异构化,则很难获得C-末端半胱氨酸肽酸。固相肽合成后C末端的多样化提出了更大的挑战,因为半胱氨酸α-立体中心倾向于在C末端羧酸活化后发生去质子化。我们在这里提出了两种通用的策略来访问C端半胱氨酸肽衍生物而没有可检测的差向异构,二酮哌嗪形成或哌啶基丙氨酸副产物。
更新日期:2017-11-16
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