VIII.—Synthetical aminoglucosides derived from d-glucosamine

The shape of D-glucosamine.

The bioactive amino monosaccharide D-glucosamine has been generated in the gas phase via laser ablation of D-glucosamine hydrochloride. Three cyclic α-(4)C1 pyranose forms have been identified using Fourier transform microwave techniques. Stereoelectronic hyperconjugative forces - essentially linked with the anomeric or gauche effect - and cooperative OH···O, OH···N and NH···O chains, extended ...

Synthesis of oseltamivir and tamiphosphor from N-acetyl-D-glucosamine.

Using N-acetyl-D-glucosamine as a starting material, the anti-influenza drugs oseltamivir and tamiphosphor were synthesized via a pivotal intermediate of aldehyde 8. An intramolecular Horner-Wadsworth-Emmons reaction was utilized to construct the highly functionalized cyclohexene ring. The existing N-acetyl group was transformed into an azido group for the subsequent aziridination, followed by ...

Metabolism of D-Glucosamine and kketyl-D- glucosamine in the Intact Rat*

It has been demonstrated that n-glucosamine and N-acetyln-glucosamine are metabolized in animal tissues to n-fructose via phosphorylated intermediates (14). It has also been shown that n-glucose is converted to n-glucosamine and incorporated into glycoproteins and mucopolysaccharides (Pll), probably through formation of uridine diphosphate derivatives as intermediates (4). Little work has been ...

Metabolism of D-glucosamine and N-acetyl-D-glucosamine in the intact rat.

It has been demonstrated that n-glucosamine and N-acetyln-glucosamine are metabolized in animal tissues to n-fructose via phosphorylated intermediates (14). It has also been shown that n-glucose is converted to n-glucosamine and incorporated into glycoproteins and mucopolysaccharides (Pll), probably through formation of uridine diphosphate derivatives as intermediates (4). Little work has been ...

THE OXIDATION OF HEXOSAMINES : d-GLUCOSAMINE AND d-GLUCOSAMINIC ACID