title: OleD Loki as a Catalyst for Tertiary Amine and Hydroxamate Glycosylation.
abstract: We describe the ability of an engineered glycosyltransferase (OleD Loki) to catalyze the N-glycosylation of tertiary-amine-containing drugs and trichostatin hydroxamate glycosyl ester formation. As such, this study highlights the first bacterial model catalyst for tertiary-amine N-glycosylation and further expands the substrate scope and synthetic potential of engineered OleDs. In addition, this work could open the door to the discovery of similar capabilities among other permissive bacterial glycosyltransferases.
authors.affiliation: Center for Pharmaceutical Research and Innovation, College of Pharmacy, University of Kentucky, 789 South Limestone Street, Lexington, KY, 40536, USA.
authors.forename: Ryan R
authors.initials: RR
authors.lastname: Hughes
authors.affiliation: Center for Pharmaceutical Research and Innovation, College of Pharmacy, University of Kentucky, 789 South Limestone Street, Lexington, KY, 40536, USA.
authors.forename: Khaled A
authors.initials: KA
authors.lastname: Shaaban
authors.affiliation: Center for Pharmaceutical Research and Innovation, College of Pharmacy, University of Kentucky, 789 South Limestone Street, Lexington, KY, 40536, USA.
authors.forename: Jianjun
authors.initials: J
authors.lastname: Zhang
authors.affiliation: Department of Chemistry, Rice University, P. O. Box 1892, MS 60, Houston, TX, 77251, USA.
authors.forename: Hongnan
authors.initials: H
authors.lastname: Cao
authors.affiliation: Department of Chemistry, Rice University, P. O. Box 1892, MS 60, Houston, TX, 77251, USA.
authors.forename: George N
authors.initials: GN
authors.lastname: Phillips
authors.affiliation: Center for Pharmaceutical Research and Innovation, College of Pharmacy, University of Kentucky, 789 South Limestone Street, Lexington, KY, 40536, USA.
authors.forename: Jon S
authors.initials: JS
authors.lastname: Thorson
mesh_terms: D000588:Amines / Q000737:chemistry / Q000378:metabolism*; D002384:Catalysis; D020134:Catalytic Domain / Q000502:physiology; D006031:Glycosylation; D016695:Glycosyltransferases / Q000737:chemistry* / Q000235:genetics; D006877:Hydroxamic Acids / Q000737:chemistry*; D008954:Models, Biological; D015394:Molecular Structure; D015202:Protein Engineering
chemical_list: D000588:Amines; D006877:Hydroxamic Acids; D016695:Glycosyltransferases
keywords: antidepressants; drug metabolism; glucuronidation; glycosyltransferases; trichostatin