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OleD Loki As a Catalyst for Tertiary Amine and Hydroxamate Glycosylation

Overview
Journal Chembiochem
Specialty Biochemistry
Date 2017 Jan 10
PMID 28067448
Citations 3
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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.

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References
1.
Tsuji N, Kobayashi M . Trichostatin C, a glucopyranosyl hydroxamate. J Antibiot (Tokyo). 1978; 31(10):939-44. DOI: 10.7164/antibiotics.31.939. View

2.
Chen D, Chen R, Wang R, Li J, Xie K, Bian C . Probing the Catalytic Promiscuity of a Regio- and Stereospecific C-Glycosyltransferase from Mangifera indica. Angew Chem Int Ed Engl. 2015; 54(43):12678-82. DOI: 10.1002/anie.201506505. View

3.
Gantt R, Peltier-Pain P, Thorson J . Enzymatic methods for glyco(diversification/randomization) of drugs and small molecules. Nat Prod Rep. 2011; 28(11):1811-53. DOI: 10.1039/c1np00045d. View

4.
Wang F, Zhou M, Singh S, Yennamalli R, Bingman C, Thorson J . Crystal structure of SsfS6, the putative C-glycosyltransferase involved in SF2575 biosynthesis. Proteins. 2013; 81(7):1277-82. PMC: 3896073. DOI: 10.1002/prot.24289. View

5.
Grass S, Lichti C, Townsend R, Gross J, St Geme 3rd J . The Haemophilus influenzae HMW1C protein is a glycosyltransferase that transfers hexose residues to asparagine sites in the HMW1 adhesin. PLoS Pathog. 2010; 6(5):e1000919. PMC: 2877744. DOI: 10.1371/journal.ppat.1000919. View