Direct oxidation of sugar nucleotides to the corresponding uronic acids: TEMPO and platinum-based procedures.
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.
Rejzek
Martin
M
Centre for Carbohydrate Chemistry, School of Chemical Sciences and Pharmacy, University of East Anglia, Norwich NR4 7TJ, UK.
Mukhopadhyay
Balaram
B
Wenzel
Cory Q
CQ
Lam
Joseph S
JS
Field
Robert A
RA
D002384:Catalysis; D003497:Cyclic N-Oxides / Q000737:chemistry*; D009702:Nucleoside Diphosphate Sugars / Q000737:chemistry*; D010084:Oxidation-Reduction; D010984:Platinum / Q000737:chemistry*; D014530:Uridine Diphosphate / Q000031:analogs & derivatives* / Q000737:chemistry; D014532:Uridine Diphosphate Glucose / Q000737:chemistry; D014535:Uridine Diphosphate Glucuronic Acid / Q000138:chemical synthesis; D014537:Uridine Diphosphate N-Acetylglucosamine / Q000737:chemistry; D014539:Uridine Diphosphate Sugars / Q000138:chemical synthesis; D014574:Uronic Acids / Q000138:chemical synthesis*
D003497:Cyclic N-Oxides; D009702:Nucleoside Diphosphate Sugars; C530748:UDP-TEMPO; D014539:Uridine Diphosphate Sugars; D014574:Uronic Acids; C046669:UDP-N-acetylglucosaminuronic acid; D014535:Uridine Diphosphate Glucuronic Acid; D010984:Platinum; D014537:Uridine Diphosphate N-Acetylglucosamine; D014530:Uridine Diphosphate; D014532:Uridine Diphosphate Glucose; C003959:TEMPO