Heterocyclic derivatives of sugars: An NMR study of the formation of 1-glycosyl-3,5-dimethyl-1H-pyrazoles from hydrazones

被引：19

作者：

Kett, WC ^{[1
]}

Batley, M ^{[1
]}

Redmond, JW ^{[1
]}

机构：

[1] MACQUARIE UNIV,SCH CHEM,N RYDE,NSW 2109,AUSTRALIA

来源：

CARBOHYDRATE RESEARCH | 1997年 / 299卷 / 03期

关键词：

sugar hydrazone; equilibria; pyrazole; sugar labelling; NMR spectroscopy;

D O I：

10.1016/S0008-6215(97)00007-4

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：

Hydrazones were prepared by treatment of monosaccharides and disaccharides with hydrazine hydrate and converted in high yield to mixtures of 1-glycosyl-3,5-dimethyl-1 H-pyrazoles by reaction with pentan-2,4-dione (acetylacetone). The isomeric products were separated by HPLC and characterized by NMR spectroscopy. This represents a new approach to the introduction of a heteroaromatic label into sugars under nonacidic and nonreducing conditions, and it is a process likely to be especially useful for glycan hydrazones obtained from glycoproteins by hydrazinolysis or beta elimination in the presence of hydrazine. (C) 1997 Elsevier Science Ltd.

引用

页码：129 / 141

页数：13

共 22 条

[1] EQUILIBRIA BETWEEN PYRANOSES AND FURANOSES .2. ALDOSES [J].