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

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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

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Publication details

The article was received on 14 Aug 2017, accepted on 07 Nov 2017 and first published on 09 Nov 2017


Article type: Edge Article
DOI: 10.1039/C7SC03553E
Citation: Chem. Sci., 2018, Advance Article
  • Open access: Creative Commons BY-NC license
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    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, Advance Article , DOI: 10.1039/C7SC03553E

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