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

Reputable Mentor II
Reputable Mentor II
Yan X, Akinnusi TO, Larsen AT, Auclair K.
Org Biomol Chem. 2011 Mar 7;9(5):1538-46.
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.
Department of Chemistry, McGill University, 801 Sherbrooke Street West, Montréal, Québec, Canada H3A 2K6.
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