Issue 2, 2018

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

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.

Graphical abstract: Epimerization-free access to C-terminal cysteine peptide acids, carboxamides, secondary amides, and esters via complimentary strategies

Supplementary files

Article information

Article type
Edge Article
Submitted
14 ago 2017
Accepted
07 nov 2017
First published
09 nov 2017
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY-NC license

Chem. Sci., 2018,9, 350-355

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

C. A. Arbour, T. D. Kondasinghe, H. Y. Saraha, Teanna L. Vorlicek and J. L. Stockdill, Chem. Sci., 2018, 9, 350 DOI: 10.1039/C7SC03553E

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