Effect of Reductones on Liver Glyoxalase Enzyme Systems

M, Iio; Okabe, Koichi; Ômura, Hirohisa

doi:10.4327/jsnfs1949.28.271

Cited by 2 publications

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“…Xylose has been reported to react with hydroxylamine to form an equilibrium mixture of the E-and Z-openchain oximes and the N-hydroxy-b-d-xylopyranosylamine (ratio about 80:18:3). [57,58] From d-xylose we obtained a similar noncrystalline mixture of the E-and Z-oximes (21) and the N-hydroxy-b-d-pyranosylamine (Scheme 2). The 1 H NMR spectrum of a solution of mixture 21 in D 2 O did not show any change over many days.…”

Section: Wwwchemeurjorgmentioning

confidence: 99%

Nitrosation of Sugar Oximes: Preparation of 2‐Glycosyl‐1‐hydroxydiazene‐2‐oxides

Brand¹,

Huhn²,

Groth³

et al. 2005

Chemistry A European J

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Oximes of glucose, xylose, lactose, fructose, and mannose have been prepared. Nitrosation of the oximes of glucose, xylose, and lactose with NaNO2/HCl afforded 2‐(β‐glycopyranosyl)‐1‐hydroxydiazene‐2‐oxides, which were isolated as salts 13, 22, and 28. Nitrosation of fructose oxime 29 furnished fructose, whereas nitrosation of mannose oxime 30 with NaNO2/HCl afforded the 1‐hydroxy‐2‐(β‐d‐mannopyranosyl)diazene‐2‐oxide 32, from which the p‐anisidinium salt 31 and the sodium salt 33 were prepared. However, nitrosation of 30 with isopentyl nitrite in aqueous solutions of CsOH or KOH resulted in the formation of the 2‐(α‐D‐mannofuranosyl)‐1‐hydroxydiazene‐2‐oxide salts 34 and 35, respectively. Methylation of the ammonium 2‐(β‐D‐glucopyranosyl)‐1‐hydroxydiazene‐2‐oxide 13 yielded the 1‐methoxy compound, which was benzoylated to afford the tetra‐O‐benzoate 14 a, the structure of which was confirmed by X‐ray diffraction analysis. From the glucose O‐methyloximes 15 and 16 the N‐methoxy‐N‐nitroso‐2,3,4,6‐tetra‐O‐acetyl‐β‐D‐glucopyranosylamine 18 was prepared. The structure of this compound was confirmed by X‐ray diffraction analysis. Treatment of acetobromoglucose with cupferron furnished the 1‐(2,3,4,6‐tetra‐O‐acetyl‐β‐D‐glucopyranosyloxy)‐2‐phenyldiazene‐2‐oxide 20.

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Section: Wwwchemeurjorgmentioning

confidence: 99%