Wc. Kett et al., HETEROCYCLIC-DERIVATIVES OF SUGARS - AN NMR-STUDY OF THE FORMATION OF1-GLYCOSYL-3,5-DIMETHYL-1H-PYRAZOLES FROM HYDRAZONES, Carbohydrate research, 299(3), 1997, pp. 129-141
Hydrazones were prepared by treatment of monosaccharides and disacchar
ides 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-dio
ne (acetylacetone). The isomeric products were separated by HPLC and c
haracterized by NMR spectroscopy. This represents a new approach to th
e introduction of a heteroaromatic label into sugars under nonacidic a
nd nonreducing conditions, and it is a process likely to be especially
useful for glycan hydrazones obtained from glycoproteins by hydrazino
lysis or beta elimination in the presence of hydrazine. (C) 1997 Elsev
ier Science Ltd.