Epimerization-free access to C-terminal cysteine peptide acids, carboxamides, secondary amides, and esters via complimentary strategies†,Chemical Science

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Epimerization-free access to C-terminal cysteine peptide acids, carboxamides, secondary amides, and esters via complimentary strategies†
Chemical Science ( IF 7.6 ) Pub Date : 2017-11-09 00:00:00 , DOI: 10.1039/c7sc03553e
Christine A Arbour ₁ , Thilini D Kondasinghe ₁ , Hasina Y Saraha ₁ , Teanna L Vorlicek ₁ , Jennifer L Stockdill ₁

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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，无差向异构化地获得 C 末端半胱氨酸肽酸、甲酰胺、仲酰胺和酯†

如果半胱氨酸 α-立体中心没有差向异构化，则很难接近 C 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-立体中心在 C 末端羧酸激活后容易发生去质子化。我们在此提出两种通用策略来获得C末端半胱氨酸肽衍生物，而不会检测到差向异构化、二酮哌嗪形成或哌啶基丙氨酸副产物。

更新日期：2017-11-09

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