SEQUENTIAL REMOVAL OF MONOSACCHARIDES FROM THE REDUCING END OF OLIGOSACCHARIDES .1. A REACTION BETWEEN HYDRAZINE AND SUGARS HAVING A GLYCOSIDIC SUBSTITUENT ON A CARBON-ATOM ADJACENT TO THE CARBONYL GROUP

被引:4
作者
BENDIAK, B [1 ]
SALYAN, ME [1 ]
PANTOJA, M [1 ]
机构
[1] UNIV WASHINGTON,SEATTLE,WA 98119
关键词
D O I
10.1016/S0040-4039(00)75790-X
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Hydrazine reacts smoothly with sugars having a glycosidic substituent when the glycosyl moiety is located on a carbon atom adjacent to an aldehyde or keto 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.
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页码:685 / 688
页数:4
相关论文
共 22 条
[1]  
[Anonymous], CARBOHYDRATES CHEM B
[2]   HYDRAZINOLYSIS-N-REACETYLATION OF GLYCOPEPTIDES AND GLYCOPROTEINS - MODEL STUDIES USING 2-ACETAMIDO-1-N-(L-ASPART-4-OYL)-2-DEOXY-BETA-D-GLUCOPYRANOSYLAMINE [J].
BENDIAK, B ;
CUMMING, DA .
CARBOHYDRATE RESEARCH, 1985, 144 (01) :1-12
[3]  
Bendiak Brad, 1992, Glycobiology, V2, P460
[4]   THE CONFIGURATION OF GLYCOSIDIC LINKAGES IN OLIGOSACCHARIDES .4. FURTHER DEGRADATIONS OF REDUCING DISACCHARIDES TO 2-O-GLYCOSYL-GLYCEROLS [J].
CHARLSON, AJ ;
GORIN, PAJ ;
PERLIN, AS .
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1957, 35 (04) :365-373
[5]   THE CONFIGURATION OF GLYCOSIDIC LINKAGES IN OLIGOSACCHARIDES .2. BY DEGRADATION OF REDUCING DISACCHARIDES TO 2-0-GLYCOSYL-GLYCEROLS [J].
CHARLSON, AJ ;
GORIN, PAJ ;
PERLIN, AS .
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1956, 34 (12) :1811-1818
[6]   FURTHER OBSERVATIONS ON THE LEAD TETRAACETATE OXIDATION OF REDUCING DISACCHARIDES [J].
CHARLSON, AJ ;
PERLIN, AS .
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1956, 34 (09) :1200-1208
[7]  
CHARLSON AJ, 1962, METHODS CARBOHYDRATE, V1, P419
[8]  
ELKHADEM H, 1967, CARBOHYD RES, V4, P225
[9]  
FISCHER E, 1884, BER, V17, P579, DOI DOI 10.1002/CBER.188401701158
[10]   IMPROVEMENTS IN THE PREPARATION OF D-ARABINOSE FROM CALCIUM D-GLUCONATE AND OF D-LYXOSE FROM CALCIUM D-GALACTONATE [J].
FLETCHER, HG ;
DIEHL, HW ;
HUDSON, CS .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1950, 72 (10) :4546-4546