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Issue 30, 2016
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Chemoselective synthesis of functional homocysteine residues in polypeptides and peptides

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Abstract

A methodology was developed for efficient, chemoselective transformation of methionine residues into stable, functional homocysteine derivatives. Methionine residues can undergo highly chemoselective alkylation reactions at low pH to yield stable sulfonium ions, which could then be selectively demethylated to give stable alkyl homocysteine residues. This mild, two-step process is chemoselective, efficient, tolerates many functional groups, and provides a means for creation of new functional biopolymers, site-specific peptide tagging, and synthesis of biomimetic and structural analogs of peptides.

Graphical abstract: Chemoselective synthesis of functional homocysteine residues in polypeptides and peptides

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Supplementary files

Article information


Submitted
09 Feb 2016
Accepted
16 Mar 2016
First published
17 Mar 2016

Chem. Commun., 2016,52, 5336-5339
Article type
Communication

Chemoselective synthesis of functional homocysteine residues in polypeptides and peptides

E. G. Gharakhanian and T. J. Deming, Chem. Commun., 2016, 52, 5336 DOI: 10.1039/C6CC01253A

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