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

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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.

http://www.ncbi.nlm.nih.gov/pmc/articles/PMC3084192/pdf/nihms1741.pdf
Department of Chemistry, McGill University, 801 Sherbrooke Street West, Montréal, Québec, Canada H3A 2K6.
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