Glucopyranosiduronates

The metabolite of 2-amino-4-phenylthiazole (used as an anaesthetic for fish) was identified (223) as 2-amino-4-phenylthiazole 2-N, -d-glucopyranosiduronic acid (71) (Scheme 50). The formation of this compound probably involves the reaction of the exocyclic nitrogen on the Open-chain form of the acid. The isolation of this metabolite is part of a very Systematic study by Japanese researchers related to the anaesthetic... 

Phenyl p-D-glucopyranosiduronic acid not phenyl p-D-glucuronoside or phenyl glucuronide H... 

In a series of studies on 2-amino-A-phenylthiazole (Piscaine), a fish anesthetic, Suzuki and co-workers (24) isolated and identified an N-glucuronide metabolite (2-amino-A-phenylthiazole-2-N-g-mono-D-glucopyranosiduronic acid) from medaka (Oryzias latipes), rainbow trout, and carp (Cyprinus oarpio) (Figure l). 

P. Florio, R. J. Thomson, A. Alafaci, S. Abo, and M. von Itzstein, Synthesis of 8 4-P-d-glucopyranosiduronic acids as mimetics of 2,3-unsaturated sialic acids for sialidase inhibition, Bioorg. Med. Chem. Lett., 9 (1999) 2065-2068. 

A number of /i-D-glucopyranosiduronic acids have been prepared from methyl 2,3,4-tri-O-acetyl-1 -bromo-1 -deoxy-/J-D-glucopyranuronate (85), a compound initially prepared by Goebel and Babers by the action of hydrogen bromide in acetic acid on methyl tetra-O-acetyl-a- or fi-D-glucopyranuronates.245... 

Compounds known to behave in this way in vivo are listed in recent reviews in this Series.1 2 The structures of some of the /3-D-glucopyranosiduronic acids isolated from urine have been proved by chemical synthesis.3 A few similar derivatives of flavones and triterpenes have been isolated from plants. D-Glucuronic acid also occurs in mammalian tissues as a constituent of acid mucopolysaccharides (aminodeoxypolysaccharides, containing uronic acid), such as hyaluronic acid, chondroitinsulfate, and heparin,4 and it is a direct precursor of L-ascorbic acid in plants and mammals.6 It is present in many of the plant polysaccharides classified as hemicelluloses6 and gums,7 and it has also been found in certain bacterial polysaccharides.4... 

Glucuronidase is universally distributed in the mammalian body, and is present in many other organisms. It hydrolyzes /3-D-glucopyranosiduronic... 

To a stirred solution of the methyl 2,3-di-0-benzyl-4-deoxy-a-D-glucopyranosiduronic acid (1.73 g, 4.65 mmol) in CH2CI2 (30 ml) was added oxalyl chloride (0.943 g, 0.65 ml, 7.43 mmol) followed by DMF (0.23 mmol) at room temperature. The resulting clear solution was stirred at room temperature for 2 h, and then concentrated in vacuo. 

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