The composition of 2-keto aldoses in organic solvents as determined by NMR spectroscopy

被引：15

作者：

Freimund, S ^{[1
]}

Köpper, S ^{[1
]}

机构：

[1] Carl von Ossietzky Univ Oldenburg, Fachbereich Chem, D-26121 Oldenburg, Germany

来源：

CARBOHYDRATE RESEARCH | 2004年 / 339卷 / 02期

关键词：

2-keto aldoses; isomeric forms; composition in solution; NMR spectroscopy;

D O I：

10.1016/j.carres.2003.11.001

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

The composition of the 2-keto aldoses D-glucosone (1), 6-deoxy-D-glucosone (2), D-allosone (3), and D-galactosone (4) in organic solvents has been determined using NMR spectroscopy. Whereas these keto aldoses form mixtures with up to 15 different isomers in water, the number of forms is significantly decreased in organic solvents. Equilibrium mixtures of 1, 2, and 4 in Me2SO, DMF, and pyridine consist to 70-90% of the prevailing alpha-1,5-pyranose form. Two bicyclic forms with a proportion of 80% are the main isomers of 3 in pyridine. Generally, forms with non-hydrated keto functions prevail in non-aqueous solutions. (C) 2003 Elsevier Ltd. All rights reserved.

引用

页码：217 / 220

页数：4

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