Of 2-acetamido-2-deoxy-D-glucose

The a anomers of 2-acetamido-2-deoxy-D-glucose and 2-acetamido-2-deoxy-D-galactose have the same nir c.d. bands in 1 1 methanol-water at 0° as the anomeric mixtures have in aqueous solution. This indicates that the anomeric configuration has little influence on the nir c.d. band. 

Buffington and Stevens measured the c.d. of 2-acetamido-2-deoxy-D-glucose as a film cast from HFIP. The spectrum is considerably more intense than that observed by Dickinson and coworkers for a solution in HFIP, but shows the same general features shifted somewhat towards the red. This vacuum-u.v. c.d. spectrum (see Fig. 18) has, at 218 nm, an intense, positive band due to the mr, an intense negative band due to the amide tttt at 200 nm, and a shoulder at 180 nm, but no other significant features down to 145 nm. 

Hough, L., and M. I. Taha The Reaction of 2-Acetamido-2-deoxy-D-glucose... 

L. Sala, C. Palopoli, and S. Signorella, Oxidation of 2-acetamido-2-deoxy-D-glucose by Cr(VI) in perchloric acid, Polyhedron, 14 (1995) 1725—1730. 

In a paper concerned primarily with the determination of neutral sugars, Richey and coworkers examined the O-trimethylsilyl derivatives of 2-acetamido-2-deoxy-D-glucose and 2-acetamido-2-deoxy-D-galactose.171 Similar methods for determining these compounds have also been used in studies on human milk,545 yeasts and bacteria,1,2 blood-group oligosaccharides,405 and urine.118 These methods were also included in a model study on the isothermal determination of sugars.256... 

Sialic acid occurs naturally as both the N-acetylated and the N-glycoloylated form, the proportion in a given environment being different from one species to another.316 Oxidation of the acetyl group to the glycoloyl group occurs after the formation of 2-acetamido-2-deoxy-D-glucose.317... 

Release of 2-Acetamido-2-deoxy-D-glucose from Glycoproteins and Glycopeptides (GP) by Use of 2-Acetamido-2-deoxy-/3-D-glucosidase... 

Halide 32 was used first, in nitromethane-benzene solution in the presence of an equimolar proportion of mercuric cyanide. It was found83 that 32 gave a disaccharide at 0-6 of a protected derivative of 2-acetamido-2-deoxy-D-glucose in good yield, with a certain degree of stereoselectivity (a /3 ratio 7 3). Complete stereospecificity was attained, leading to the desired a-linked disaccharides, when the partially acylated bromide 33 was condensed with a number of different nucleophiles.66,83,84,93-95 A mechanism was postulated83 to explain the... 

At room temperature during 2 h, the reaction was conducted with 9.5 g of 2-acetamido-2-deoxy-D-glucose by the same method and procedure [reported in Ref. 96]. After recrystallization of die product (lOg, 90%), the final filtrate was chromatographed on a column of silicic acid (30 g) with 30 1 chloroform/ methanoL... 

UDP-Glc, or UDP-Gal, or both, into the polymer is necessary, prior to the incorporation of 2-acetamido-2-deoxy-D-glucose. 

These derivatives of 2-acetamido-2-deoxy-/ -D-glucose were stable to 0.1M NaOH, 0.3M NaBH4 at 20°C for 24 hours, but the corresponding amides were partially cleaved (62). 

Oxidation of 2-acetamido-2-deoxy-D-glucose derivatives with hypoiodite at 0° proceeds quantitatively, without side reactions, and is satisfactory as a procedure for end-group assay in oligosaccharides containing amino sugar residues.177 The possibility that (1 —> 3)-linked disaccharides may be degraded under the reaction conditions must not be overlooked. 

Lactonization is not obligatory, as the byproduct formed in the reaction of 2-acetamido-2-deoxy-D-glucose with methoxycarbonyl-methylenetriphenylphosphorane was proved67 to have structure 134. This compound rapidly consumes one mole of periodate per mole, and shows signals at r 7.95 p.p.m. (doublet) and r 6.15 p.p.m. in its n.m.r. spectrum, corresponding to the a-methylenic and the ester group, respectively. Use of 2-acetamido-4,6-0-benzylidene-2-deoxy-D-arabino-hexose instead of the unprotected sugar does not prevent... 

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