Issue 13, 2011

Alternating chemical ligation reactivity of S-acyl peptides explained with theory and computations

Abstract

Previously discovered alternating reactivity of S-acyl di-, tri-, and tetrapeptide in internal chemical ligation reactions is rationalised using conformational search, virtual screening methods and quantum chemical calculations. Conformational preorganisation is shown to be the major controller of reactivity, with hydrogen bonding providing additional stabilisation for the tetrapeptide structure.

Graphical abstract: Alternating chemical ligation reactivity of S-acyl peptides explained with theory and computations

Article information

Article type
Communication
Submitted
05 Apr 2011
Accepted
26 Apr 2011
First published
26 Apr 2011

Org. Biomol. Chem., 2011,9, 4756-4759

Alternating chemical ligation reactivity of S-acyl peptides explained with theory and computations

A. A. Oliferenko and A. R. Katritzky, Org. Biomol. Chem., 2011, 9, 4756 DOI: 10.1039/C1OB05536D

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