OleD Loki as a Catalyst for Tertiary Amine and Hydroxamate Glycosylation

Ryan R. Hughes; Khaled A. Shaaban; Jianjun Zhang; Hongnan Cao; George N. Phillips; Jon S. Thorson

doi:10.1002/cbic.201600676

OleD Loki as a Catalyst for Tertiary Amine and Hydroxamate Glycosylation

Ryan R. Hughes
, Khaled A. Shaaban
, Jianjun Zhang
, Hongnan Cao
, George N. Phillips
, Jon S. Thorson

Research output: Contribution to journal › Article › peer-review

7 Scopus citations

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.

Original language	English
Pages (from-to)	363-367
Number of pages	5
Journal	ChemBioChem
Volume	18
Issue number	4
DOIs	https://doi.org/10.1002/cbic.201600676
State	Published - Feb 16 2017

Bibliographical note

Publisher Copyright:
© 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim

Funding

Funders	Funder number
National Institute of General Medical Sciences	U01GM098248
National Institute of General Medical Sciences

Keywords

antidepressants
drug metabolism
glucuronidation
glycosyltransferases
trichostatin

ASJC Scopus subject areas

Biochemistry
Molecular Medicine
Molecular Biology
Organic Chemistry

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10.1002/cbic.201600676

Cite this

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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.",

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author = "Hughes, \{Ryan R.\} and Shaaban, \{Khaled A.\} and Jianjun Zhang and Hongnan Cao and Phillips, \{George N.\} and Thorson, \{Jon S.\}",

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doi = "10.1002/cbic.201600676",

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AU - Hughes, Ryan R.

AU - Shaaban, Khaled A.

AU - Zhang, Jianjun

AU - Cao, Hongnan

AU - Phillips, George N.

AU - Thorson, Jon S.

PY - 2017/2/16

Y1 - 2017/2/16

N2 - 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.

AB - 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.

KW - antidepressants

KW - drug metabolism

KW - glucuronidation

KW - glycosyltransferases

KW - trichostatin

UR - https://www.scopus.com/pages/publications/85008429043

UR - https://www.scopus.com/pages/publications/85008429043#tab=citedBy

U2 - 10.1002/cbic.201600676

DO - 10.1002/cbic.201600676

M3 - Article

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AN - SCOPUS:85008429043

SN - 1439-4227

VL - 18

SP - 363

EP - 367

JO - ChemBioChem

JF - ChemBioChem

IS - 4

ER -

OleD Loki as a Catalyst for Tertiary Amine and Hydroxamate Glycosylation

Abstract

Bibliographical note

Funding

Keywords

ASJC Scopus subject areas

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