title: Synthesis of 4'-aminopantetheine and derivatives to probe aminoglycoside N-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.
authors.affiliation: Department of Chemistry, McGill University, 801 Sherbrooke Street West, Montréal, Québec, Canada H3A 2K6.
authors.forename: Xuxu
authors.initials: X
authors.lastname: Yan
authors.forename: T Olukayode
authors.initials: TO
authors.lastname: Akinnusi
authors.forename: Aaron T
authors.initials: AT
authors.lastname: Larsen
authors.forename: Karine
authors.initials: K
authors.lastname: Auclair
mesh_terms: D000123:Acetyltransferases / Q000737:chemistry / Q000378:metabolism*; D016984:Enterococcus faecium / Q000201:enzymology*; D008958:Models, Molecular; D015394:Molecular Structure; D010204:Pantetheine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000378:metabolism; D011485:Protein Binding; D013379:Substrate Specificity
chemical_list: C557399:4'-aminopantetheine; D010204:Pantetheine; D000123:Acetyltransferases; C056532:aminoglycoside N(6')-acetyltransferase