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Regio‐ and Chemoselective 6′‐N‐Derivatization of Aminoglycosides: Bisubstrate Inhibitors as Probes To Study Aminoglycoside 6′‐ N ‐Acetyltransferases
Author(s) -
Gao Feng,
Yan Xuxu,
Baettig Oliver M.,
Berghuis Albert M.,
Auclair Karine
Publication year - 2005
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200501399
Subject(s) - acetyltransferases , aminoglycoside , acetyltransferase , chemistry , regioselectivity , derivatization , enzyme , combinatorial chemistry , acetylation , antibiotics , biochemistry , stereochemistry , chromatography , mass spectrometry , catalysis , gene
Complex nanomolar inhibitors in one pot : Aminoglycoside–coenzyme A derivatives were prepared through an efficient regioselective 6′‐N modification of aminoglycosides (see scheme). These bisubstrates show tight‐binding competitive inhibition of aminoglycoside 6′‐ N ‐acetyltransferase, an enzyme involved in antibiotic resistance.