Issue 5, 2011

Synthesis of 4′-aminopantetheine and derivatives to probeaminoglycosideN-6′-acetyltransferase

Abstract

A convenient synthesis of 4′-aminopantetheine from commercial D-pantethine is reported. The amino group was introduced by reductive amination in order to avoid substitution at a sterically congested position. Derivatives of 4′-aminopantetheine were also prepared to evaluate the effect of O-to-N substitution on inhibitors of the resistance-causing enzyme aminoglycoside N-6′-acetyltransferase. The biological results combined with docking studies indicate that in spite of its reported unusual flexibility and ability to adopt different folds, this enzyme is highly specific for AcCoA.

Graphical abstract: Synthesis of 4′-aminopantetheine and derivatives to probe aminoglycoside N-6′-acetyltransferase

Supplementary files

Article information

Article type
Paper
Submitted
11 Nov 2010
Accepted
23 Nov 2010
First published
23 Nov 2010

Org. Biomol. Chem., 2011,9, 1538-1546

Synthesis of 4′-aminopantetheine and derivatives to probe aminoglycoside N-6′-acetyltransferase

X. Yan, T. O. Akinnusi, A. T. Larsen and K. Auclair, Org. Biomol. Chem., 2011, 9, 1538 DOI: 10.1039/C0OB01018A

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