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Issue 35, 2015
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Acceleration of thiol additive-free native chemical ligation by intramolecular S → S acyl transfer

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Abstract

Peptide–mercaptopropionylcysteine (MPA–Cys) thioesters show a surprisingly high reactivity in native chemical ligation (NCL) and allow thiol-additive free reactions. This facilitates sequential NCL reactions and ligation–desulfurization reactions in one-pot formats. The synthetic utility is demonstrated by the synthesis of a SH3 domain.

Graphical abstract: Acceleration of thiol additive-free native chemical ligation by intramolecular S → S acyl transfer

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Supplementary files

Article information


Submitted
16 Feb 2015
Accepted
27 Mar 2015
First published
27 Mar 2015

Chem. Commun., 2015,51, 7554-7557
Article type
Communication
Author version available

Acceleration of thiol additive-free native chemical ligation by intramolecular S → S acyl transfer

J. Schmalisch and O. Seitz, Chem. Commun., 2015, 51, 7554
DOI: 10.1039/C5CC01447F

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