A simple strategy for glycosyltransferase-catalyzed aminosugar nucleotide synthesis

Jianjun Zhang; Shanteri Singh; Ryan R. Hughes; Maoquan Zhou; Manjula Sunkara; Andrew J. Morris; Jon S. Thorson

doi:10.1002/cbic.201300779

A simple strategy for glycosyltransferase-catalyzed aminosugar nucleotide synthesis

Jianjun Zhang, Shanteri Singh, Ryan R. Hughes, Maoquan Zhou, Manjula Sunkara, Andrew J. Morris, Jon S. Thorson

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

18 Scopus citations

Abstract

A set of 2-chloro-4-nitrophenyl glucosamino-/xylosaminosides were synthesized and assessed as potential substrates in the context of glycosyltransferase-catalyzed formation of the corresponding UDP/TDP-α-D-glucosamino-/xylosaminosugars and in single-vessel model transglycosylation reactions. This study highlights a robust platform for aminosugar nucleotide synthesis and reveals OleD Loki to be a proficient catalyst for U/TDP-aminosugar synthesis and utilization. 2-Chloro-4-nitrophenyl glucosamine-/xylosaminosides were synthesized and assessed as potential substrates for glycosyltransferase-catalyzed formation of the corresponding UDP/TDP-α-D-glucosamino-/xylosaminosugars and in single-vessel model transglycosylation reactions. This study highlights a robust platform for aminosugar nucleotide synthesis and reveals OleD Loki as a proficient catalyst for U/TDP-aminosugar synthesis.

Original language	English
Pages (from-to)	647-651
Number of pages	5
Journal	ChemBioChem
Volume	15
Issue number	5
DOIs	https://doi.org/10.1002/cbic.201300779
State	Published - Mar 21 2014

Keywords

carbohydrates
enzymes
glycobiology
glycorandomization
glycosides
glycosylation

ASJC Scopus subject areas

Biochemistry
Molecular Medicine
Molecular Biology
Organic Chemistry

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10.1002/cbic.201300779

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title = "A simple strategy for glycosyltransferase-catalyzed aminosugar nucleotide synthesis",

abstract = "A set of 2-chloro-4-nitrophenyl glucosamino-/xylosaminosides were synthesized and assessed as potential substrates in the context of glycosyltransferase-catalyzed formation of the corresponding UDP/TDP-α-D-glucosamino-/xylosaminosugars and in single-vessel model transglycosylation reactions. This study highlights a robust platform for aminosugar nucleotide synthesis and reveals OleD Loki to be a proficient catalyst for U/TDP-aminosugar synthesis and utilization. 2-Chloro-4-nitrophenyl glucosamine-/xylosaminosides were synthesized and assessed as potential substrates for glycosyltransferase-catalyzed formation of the corresponding UDP/TDP-α-D-glucosamino-/xylosaminosugars and in single-vessel model transglycosylation reactions. This study highlights a robust platform for aminosugar nucleotide synthesis and reveals OleD Loki as a proficient catalyst for U/TDP-aminosugar synthesis.",

keywords = "carbohydrates, enzymes, glycobiology, glycorandomization, glycosides, glycosylation",

author = "Jianjun Zhang and Shanteri Singh and Hughes, {Ryan R.} and Maoquan Zhou and Manjula Sunkara and Morris, {Andrew J.} and Thorson, {Jon S.}",

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AU - Zhang, Jianjun

AU - Singh, Shanteri

AU - Hughes, Ryan R.

AU - Zhou, Maoquan

AU - Sunkara, Manjula

AU - Morris, Andrew J.

AU - Thorson, Jon S.

PY - 2014/3/21

Y1 - 2014/3/21

N2 - A set of 2-chloro-4-nitrophenyl glucosamino-/xylosaminosides were synthesized and assessed as potential substrates in the context of glycosyltransferase-catalyzed formation of the corresponding UDP/TDP-α-D-glucosamino-/xylosaminosugars and in single-vessel model transglycosylation reactions. This study highlights a robust platform for aminosugar nucleotide synthesis and reveals OleD Loki to be a proficient catalyst for U/TDP-aminosugar synthesis and utilization. 2-Chloro-4-nitrophenyl glucosamine-/xylosaminosides were synthesized and assessed as potential substrates for glycosyltransferase-catalyzed formation of the corresponding UDP/TDP-α-D-glucosamino-/xylosaminosugars and in single-vessel model transglycosylation reactions. This study highlights a robust platform for aminosugar nucleotide synthesis and reveals OleD Loki as a proficient catalyst for U/TDP-aminosugar synthesis.

AB - A set of 2-chloro-4-nitrophenyl glucosamino-/xylosaminosides were synthesized and assessed as potential substrates in the context of glycosyltransferase-catalyzed formation of the corresponding UDP/TDP-α-D-glucosamino-/xylosaminosugars and in single-vessel model transglycosylation reactions. This study highlights a robust platform for aminosugar nucleotide synthesis and reveals OleD Loki to be a proficient catalyst for U/TDP-aminosugar synthesis and utilization. 2-Chloro-4-nitrophenyl glucosamine-/xylosaminosides were synthesized and assessed as potential substrates for glycosyltransferase-catalyzed formation of the corresponding UDP/TDP-α-D-glucosamino-/xylosaminosugars and in single-vessel model transglycosylation reactions. This study highlights a robust platform for aminosugar nucleotide synthesis and reveals OleD Loki as a proficient catalyst for U/TDP-aminosugar synthesis.

KW - carbohydrates

KW - enzymes

KW - glycobiology

KW - glycorandomization

KW - glycosides

KW - glycosylation

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A simple strategy for glycosyltransferase-catalyzed aminosugar nucleotide synthesis

Abstract

Keywords

ASJC Scopus subject areas

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