Epimerization-free Access to C-terminal Cysteine Peptide Acids, Carboxamides, Secondary Amides, and Esters Complimentary Strategies

Overview

Journal Chem Sci

Publisher Royal Society of Chemistry

Specialty Chemistry

Date 2018 Apr 10

PMID 29629104

Citations 7

Authors

Christine A Arbour

Thilini D Kondasinghe

Hasina Y Saraha

Teanna L Vorlicek

Jennifer L Stockdill

Affiliations

Soon will be listed here.

Abstract

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.

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