Syntheses and structures of anomeric quaternary ammonium β-glucosides and comments on the anomeric C–N bond lengths

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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OleD Loki as a Catalyst for Tertiary Amine and Hydroxamate Glycosylation

Hughes

Shaaban

Zhang

et al. 2017

ChemBioChem

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ChemInform Abstract: Syntheses and Structures of Anomeric Quaternary Ammonium β‐Glucosides and Comments on the Anomeric C—N Bonds Lengths.

et al. 2009

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Carbohydrates U 0500Syntheses and Structures of Anomeric Quaternary Ammonium β-Glucosides and Comments on the Anomeric C-N Bonds Lengths. -Two general methods for the synthesis of tertiary glycosylamines and their quaternization are presented. One approach involves the reductive N,N-dimethylation of a protected anomeric glycosylamine, quaternization with alkyl halides, and deacetylation without loss of the ammonium group. The other is based on the direct reaction of glucose or 6-O-trityl glucose with a secondary amine, followed by protection and quaternization with a triflate. -(IDDON, L.; BRAGG, R. A.; HARDING, J. R.; PIDATHALA, C.; BACSA, J.; KIRBY, A. J.; STACHULSKI*, A. V.; Tetrahedron 65 (2009) 32, 6396-6402; Robert Robinson Lab., Dep. Chem., Univ. Liverpool, Liverpool L69 7ZD, UK; Eng.) -Klein 47-178

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Application of trityl moieties in chemical processes: part I

et al. 2020

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Syntheses and structures of anomeric quaternary ammonium β-glucosides and comments on the anomeric C–N bond lengths

Cited by 8 publications

References 33 publications

OleD Loki as a Catalyst for Tertiary Amine and Hydroxamate Glycosylation

OleD Loki as a Catalyst for Tertiary Amine and Hydroxamate Glycosylation

ChemInform Abstract: Syntheses and Structures of Anomeric Quaternary Ammonium β‐Glucosides and Comments on the Anomeric C—N Bonds Lengths.

Application of trityl moieties in chemical processes: part I

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