Glucosamine periodate oxidation

Besides amino acids, labeled saa harides are suitable for the labeling of glycoproteins. In this manner, glycoproteins have been labeled with H-mannose H-glucosamine N-acetylmanosamine Saccharides may also be allowed to react with proteins after periodate oxidation... 

Periodate oxidations of N-acetyldidesoxydihydrostreptobiosamine indicated a pyranose ring structure for the N-methyl-n-glucosamine por-... 

Section II,A Periodate oxidation of D-glucosamine, followed by reaction of the product with ammonium acetate and formaldehyde in the presence of Cu(II), has provided a route of L-eryt/iro- 8-hydroxyhistidine. ° A... 

During the elucidation of the structure of mannosidostreptomycin by methylation. Fried and Stavely isolated two derivatives of a dimethyl ether of iV-methyl-L-glucosamine. In order to compare their physical constants with those of a known compound in the n-series. Fried and Walz prepared derivatives of 2-deoxy-3,6-di-0-methyl-2-methylamino-n-glucose. The addition of methylamine and hydrogen cyanide to 2,5-di-0-methyl-D-arabinose (prepared by the periodate oxidation of 3,6-di-O-methyl-D-glucose) was followed by hydrolysis, and jdelded a mixture of a dextro- and a levo-rotatory acid. The dextrorotatory product was con-... 

Studies of the periodate oxidation of heparin and of its product of degradation have also been used as a basis for proposing various chemical structures. The lack of precision of this method, and the erroneous conclusion derived from similar studies on other glycosaminoglycuronoglycans, render the structural allocation uncertain. The liberation of ammonia by periodate oxidation of an A -desulfated heparin suggests, however, the absence of linkage at position 3 of the glucosamine residue . ... 

In a study of the oxidation of 2-amino-2-deoxy-D-glucose (D-glucosamine) derivatives, Neuberger12 obtained better results using sodium metaperiodate (at its accompanying pH of 3 to 4) than with periodic acid at lower pH values and a pH of 4.5 was found by Jeanloz and Forchielli78a to be optimal for these derivatives. 

Action of dilute sulfuric acid for a short period of time afforded a crystalline disaccharide (Vb), in a 20 to 30 % yield. It contained equal amounts of d-glucosamine and D-glucuronic add, and a free amino group. Esterification of the carboxyl group, followed by oxidation with mercuric oxide, gave the... 

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