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

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...

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Bibliographic Details
Published in:Chemical science (Cambridge) 2018-01, Vol.9 (2), p.350-355
Main Authors: Arbour, Christine A, Kondasinghe, Thilini D, Saraha, Hasina Y, Vorlicek, Teanna L, Stockdill, Jennifer L
Format: Article
Language:English
Subjects:
Amides
Chemistry
Cysteine
Esters
Peptides
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Summary: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.
ISSN:2041-6520
2041-6539
DOI:10.1039/c7sc03553e