Direct oxidation of sugar nucleotides to the corresponding uronic acids: TEMPO and platinum-based procedures

Martin Rejzek; Balaram Mukhopadhyay; Cory Q. Wenzel; Joseph S. Lam; Robert A. Field

doi:10.1016/j.carres.2006.10.016

Direct oxidation of sugar nucleotides to the corresponding uronic acids: TEMPO and platinum-based procedures

Martin Rejzek
, Balaram Mukhopadhyay
, Cory Q. Wenzel
, Joseph S. Lam
, Robert A. Field

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

21 Citations (Scopus)

Abstract

The direct oxidation of UDP-α-d-glucose and UDP-N-acetyl-α-d-glucosamine to the corresponding uronic acids was explored using either TEMPO or platinum-catalysed oxidation with molecular oxygen. Whilst TEMPO-based procedures gave rise to substantial over-oxidation and/or degradation of UDP-glucose, oxidation of UDP-N-acetyl-glucosamine to UDP-N-acetyl-glucosaminuronic acid was achieved with >90% conversion and ca. 65% isolated yield using a platinum-catalysed procedure.

Original language	English
Pages (from-to)	460-466
Number of pages	7
Journal	Carbohydrate Research
Volume	342
Issue number	3-4
Early online date	25 Oct 2006
DOIs	https://doi.org/10.1016/j.carres.2006.10.016
Publication status	Published - 26 Feb 2007

Keywords

Oxidation
Platinum
Sugar nucleotide
TEMPO
Uronic acid

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10.1016/j.carres.2006.10.016

Cite this

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title = "Direct oxidation of sugar nucleotides to the corresponding uronic acids: TEMPO and platinum-based procedures",

abstract = "The direct oxidation of UDP-α-d-glucose and UDP-N-acetyl-α-d-glucosamine to the corresponding uronic acids was explored using either TEMPO or platinum-catalysed oxidation with molecular oxygen. Whilst TEMPO-based procedures gave rise to substantial over-oxidation and/or degradation of UDP-glucose, oxidation of UDP-N-acetyl-glucosamine to UDP-N-acetyl-glucosaminuronic acid was achieved with >90\% conversion and ca. 65\% isolated yield using a platinum-catalysed procedure.",

keywords = "Oxidation, Platinum, Sugar nucleotide, TEMPO, Uronic acid",

author = "Martin Rejzek and Balaram Mukhopadhyay and Wenzel, \{Cory Q.\} and Lam, \{Joseph S.\} and Field, \{Robert A.\}",

note = "Acknowledgements: We thank the BBSRC and the EPSRC for financial support and the EPSRC Mass Spectrometry Service, University of Wales, Swansea for invaluable support. We also acknowledge the support from the Canadian Institutes of Health Research in the form of an operating grant (MOP-14687) to J.S.L. who holds a Canada Research Chair in Cystic Fibrosis and Microbial Glycobiology. Dr. A. H. Haines is thanked for informative discussions.",

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AU - Rejzek, Martin

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AU - Wenzel, Cory Q.

AU - Lam, Joseph S.

AU - Field, Robert A.

N1 - Acknowledgements: We thank the BBSRC and the EPSRC for financial support and the EPSRC Mass Spectrometry Service, University of Wales, Swansea for invaluable support. We also acknowledge the support from the Canadian Institutes of Health Research in the form of an operating grant (MOP-14687) to J.S.L. who holds a Canada Research Chair in Cystic Fibrosis and Microbial Glycobiology. Dr. A. H. Haines is thanked for informative discussions.

PY - 2007/2/26

Y1 - 2007/2/26

N2 - The direct oxidation of UDP-α-d-glucose and UDP-N-acetyl-α-d-glucosamine to the corresponding uronic acids was explored using either TEMPO or platinum-catalysed oxidation with molecular oxygen. Whilst TEMPO-based procedures gave rise to substantial over-oxidation and/or degradation of UDP-glucose, oxidation of UDP-N-acetyl-glucosamine to UDP-N-acetyl-glucosaminuronic acid was achieved with >90% conversion and ca. 65% isolated yield using a platinum-catalysed procedure.

AB - The direct oxidation of UDP-α-d-glucose and UDP-N-acetyl-α-d-glucosamine to the corresponding uronic acids was explored using either TEMPO or platinum-catalysed oxidation with molecular oxygen. Whilst TEMPO-based procedures gave rise to substantial over-oxidation and/or degradation of UDP-glucose, oxidation of UDP-N-acetyl-glucosamine to UDP-N-acetyl-glucosaminuronic acid was achieved with >90% conversion and ca. 65% isolated yield using a platinum-catalysed procedure.

KW - Oxidation

KW - Platinum

KW - Sugar nucleotide

KW - TEMPO

KW - Uronic acid

UR - https://www.scopus.com/pages/publications/33846509242

U2 - 10.1016/j.carres.2006.10.016

DO - 10.1016/j.carres.2006.10.016

M3 - Article

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AN - SCOPUS:33846509242

SN - 0008-6215

VL - 342

SP - 460

EP - 466

JO - Carbohydrate Research

JF - Carbohydrate Research

IS - 3-4

ER -

Direct oxidation of sugar nucleotides to the corresponding uronic acids: TEMPO and platinum-based procedures

Abstract

Keywords

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