Inversion of the anomeric configuration of the transferred sugar during inactivation of the macrolide antibiotic oleandomycin catalyzed by a macrolide glycosyltransferase

FEBS Letters

Carbajo, Rodrigo J.¹  Salas, José A.²  Quirós, Luis M.² 

[1] Departamento de Quı́mica Orgánica e Inorgánica, Universidad de Oviedo, 33006 Oviedo, Spain;Departamento de Biologı́a Funcional, Universidad de Oviedo, 33006 Oviedo, Spain

关键词: Glycosyltransferase;    Macrolide;    Oleandomycin;   

DOI  :  10.1016/S0014-5793(00)01721-X

学科分类：生物化学/生物物理

来源: John Wiley & Sons Ltd.

【 摘 要 】

Macrolides are a group of antibiotics structurally characterized by a macrocyclic lactone to which one or several deoxy-sugar moieties are attached. The sugar moieties are transferred to the different aglycones by glycosyltransferases (GTF). The OleI GTF of an oleandomycin producer, Streptomyces antibioticus, catalyzes the inactivation of this macrolide by glycosylation. The product of this reaction was isolated and its structure elucidated. The donor substrate of the reaction was UDP-α-D-glucose, but the reaction product showed a β-glycosidic linkage. The inversion of the anomeric configuration of the transferred sugar and other data about the kinetics of the reaction and primary structure analysis of several GTFs are compatible with a reaction mechanism involving a single nucleophilic substitution at the sugar anomeric carbon in the catalytic center of the enzyme.

【 授权许可】

Unknown