Glucose pyrrole structure

The authors confirmed the structure by heating equimolecular amounts of pyrrole and A -acetylimi-dazole. It was identified by Kobayasi and Fujimaki (1965b) when hydroxyproline and glucose were heated at temperatures ranging from 120 to 200 °C. 

In the experiments first described, 2-amino-2-deoxy-D-glucose was heated with an excess of the /3-dicarbonyl compound in the absence of solvent. The product so obtained from ethyl acetoacetate, m.p. 142°, [a]n 49.7°, had an analysis corresponding to that for ethyl 2-methyl-5-(D-ara6mo-tetrahydroxybutyl)pyrrole-3-carboxylate and was considered to have this structure (1). In the reaction with 2,4-pentanedione, a material (m.p. 98°, Md — 25.1°) was obtained which was described as 3-acetyl-2-methyl-5-(D-ara5fno-tetrahydroxybutyl)pyrrole (2). Boyer and Furth" repeated the latter reaction, but in methanol solution, and obtained a product, m.p. 133°, whose analytical data were in agreement with those for structure (2). 

Base-catalyzed reactions of amino sugars with 2,4-pentanedione in a nonaqueous solvent (piperidine-triethylamine-methanol) have also been reported. The products obtained under these conditions from 2-amino-2-deoxy-D-glucose are 3-acetyl-2-methyl-5-(D-ami)OTo-tetrahydroxybutyl)-pyrrole (2) (in about 90% yield) and 2-deoxy-2-n(4-oxopent-2-enyl)-amino]-D-glucose (28). Proofs that structure (28) is correct were (a) the ultraviolet absorption, typical of a -amino a,j3-unsaturated ketone, (b) a positive test with the ferric chloride reagent, and (c) quantitative... 

Mediators covalently bound to or complexed with conducting and other polymers have been termed wires. Wired enzyme glucose electrodes were produced by the electropolymerization of (ferrocenyl)amidopropyl pyrrole (FAPP Fig. 6, structure 1) in the pre.sence of glucose oxidase [95], FAPP was synthesized by using l,r-carbonyl diimidazole to link ferrocenecarboxylic acid to A -(3-aminopropyl) pyrrole. The electropolymerization of Os(2,2 -bipyridine)2(3-pyrrol-l-ylmethylpyridine)Cr (Fig. 6, structure 2), N-methylpyrrole, and pyrrole-modified... 

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