Epimerization-free access to C-terminal cysteine peptide acids, carboxamides, secondary amides, and esters via complimentary strategies. Issue 2 (16th November 2017)

• Record Type: Journal Article
• Authors: Arbour, Christine A.; Kondasinghe, Thilini D.; Saraha, Hasina Y.; Vorlicek, Teanna L.; Stockdill, Jennifer L.
• Is Part Of: Chemical science. Volume 9:Issue 2(2018)
• Page Start: 350
• Page End: 355
• Publication Date: 2017-11-16
• Subjects: Chemistry -- Periodicals; 540.5
• DOI: 10.1039/c7sc03553e
• Languages: English
• ISSNs: 2041-6520

Abstract

Abstract : We present a convenient method for the diversification of peptides bearing cysteine at the C-terminus that proceeds to form a variety of carboxylic acid, carboxamide, 2° amide, and ester terminated peptides without any detectable epimerization of the α-stereocenter. 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.