Incorporation of N-acetyl-D-glucosamine from UDP-N-acetyl-D-glucosamine by isolated membranes of Bacillus subtilis. Identification of undecaprenyl poly(N-acetylglucosaminyl pyrophosphate).
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Transport and incorporation of N-acetyl-D-glucosamine in Bacillus subtilis.
Bacillus subtilis 168 has been found to possess a high-affinity transport system for N-acetyl-D-glucosamine (GlcNAC). The Km for uptake was approximately 3.7 microM GlcNAc, regardless of the nutritional background of the cells. Apparent increases in Vmax were noted when the bacteria were grown in the presence of GlcNAc. The uptake of GlcNAc by B. subtilis was highly stereoselective; D-glucose, ...
متن کاملSynthesis 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 ...
متن کاملMetabolism 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 ...
متن کاملChemoenzymatic synthesis of N-acetyl-D-neuraminic acid from N-acetyl-D-glucosamine by using the spore surface-displayed N-acetyl-D-neuraminic acid aldolase.
Chemoenzymatic synthesis of N-acetyl-d-neuraminic acid from N-acetyl-d-glucosamine using the spore surface-displayed N-acetyl-d-neuraminic acid aldolase at a high concentration (53.9 g liter(-1)) was achieved in this study. Thus, displaying a target enzyme on the surface of spores might be an alternative for integration of biocatalytic conversion into chemical synthesis.
متن کاملIs N-acetyl-d-glucosamine a rigid 4C1 chair?
Understanding microsecond-timescale dynamics is crucial to establish three-dimensional (3D) structure-activity relationships in sugars but has been intractable to experiments and simulations. As a consequence, whether arguably the most important chemical scaffold in glycobiology, N-acetyl-d-glucosamine (GlcNAc), deviates from a rigid (4)C(1) chair is unknown. Here, conformer populations and exc...
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ژورنال
عنوان ژورنال: Journal of Biological Chemistry
سال: 1977
ISSN: 0021-9258
DOI: 10.1016/s0021-9258(17)40241-9