Sequential removal of monosaccharides from the reducing end of oligosaccharides. I. A reaction between hydrazine and sugars having a glycosidic substituent on a carbon atom adjacent to the carbonyl group
✍ Scribed by Brad Bendiak; Mary Ellen Salyan; Mario Pantoja
- Book ID
- 104215557
- Publisher
- Elsevier Science
- Year
- 1994
- Tongue
- French
- Weight
- 292 KB
- Volume
- 35
- Category
- Article
- ISSN
- 0040-4039
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✦ Synopsis
Hydrazine reacts smoothly v&h sugars having a glycosidic SubstiNent when the glycosyl moiety is located on a carbon atom adjacent to au aldehyde or lceto group. resulting in cleavage of the glycosidic linkage. In excess hydrazine. the released glycoside forms a hydrazone from which the reducing sugar may be recovered in high yields. Reported herein is a novel cleavage of a glycosidic linkage when the glycosyl moiety is located on a carbon atom adjacent to an aldehyde or keto function.' In the development of a methodology for the controlled sequential removal of monosaccharides from the reducing end of oligosaccharides, our objective has been N restrict the chemistry to the reducing monosaccharide in such a way as to first, introduce an aldehyde or keto group adjacent to the glycosidic linkage,2 and second, cleave the glycosidic bond through reaction with a hydrazino compound, as depicted in the example in Scheme I.