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

Carbohydr Res. 2007 Feb 26;342(3-4):460-6. doi: 10.1016/j.carres.2006.10.016. Epub 2006 Oct 25.

Authors

Martin Rejzek¹, Balaram Mukhopadhyay, Cory Q Wenzel, Joseph S Lam, Robert A Field

Affiliation

¹ Centre for Carbohydrate Chemistry, School of Chemical Sciences and Pharmacy, University of East Anglia, Norwich NR4 7TJ, UK.

PMID: 17087923
DOI: 10.1016/j.carres.2006.10.016

Abstract

The direct oxidation of UDP-alpha-d-glucose and UDP-N-acetyl-alpha-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.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Catalysis
Cyclic N-Oxides / chemistry*
Nucleoside Diphosphate Sugars / chemistry*
Oxidation-Reduction
Platinum / chemistry*
Uridine Diphosphate / analogs & derivatives*
Uridine Diphosphate / chemistry
Uridine Diphosphate Glucose / chemistry
Uridine Diphosphate Glucuronic Acid / chemical synthesis
Uridine Diphosphate N-Acetylglucosamine / chemistry
Uridine Diphosphate Sugars / chemical synthesis
Uronic Acids / chemical synthesis*

Substances

Cyclic N-Oxides
Nucleoside Diphosphate Sugars
UDP-TEMPO
Uridine Diphosphate Sugars
Uronic Acids
UDP-N-acetylglucosaminuronic acid
Uridine Diphosphate Glucuronic Acid
Platinum
Uridine Diphosphate N-Acetylglucosamine
Uridine Diphosphate
Uridine Diphosphate Glucose
TEMPO