Issue 35, 2015
From the journal:

Chemical Communications

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

J. Schmalischa  and  O. Seitz*a  

* Corresponding authors

a Humboldt-Universität zu Berlin, Institut für Chemie, Brook-Taylor-Str. 2, 12489 Berlin, Germany
E-mail: oliver.seitz@chemie.hu-berlin.de
Fax: +49 30-2093-7266
Tel: +49 30 2093 7446

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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Article information

DOI
https://doi.org/10.1039/C5CC01447F
Article type
Communication
Submitted
16 Feb 2015
Accepted
27 Mar 2015
First published
27 Mar 2015

Chem. Commun., 2015,51, 7554-7557

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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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