JV-acetyl-D-glucosamine

Vasella has applied the concept of anomeric anion stabilization by a nitro group to the /3-D-JV-acetyl-D-glucosamine derivative 177, available in four steps from N-acetyl-n-glucosamine [52] (Scheme 39). Reaction of the tetraethylammonium nitronate derived from 177 with aldehyde 178 provides anti-179 which then undergoes stereoselectively reduction (see Sect. 2.2.1) to provide -C-glycoside 180, intermediate in a synthesis of N-acetyl-neuraminic acid. 

JV-acetyl-D-glucosamine) (27) or, preferably, from the 3-0-substituted derivatives. It is an intermediate in the Morgan-Elson color reaction (see Section VII, la p. 202). 

J. P. Privat, F. Delmotte, and M. Monsigny, Protein-sugar interactionsassociation of beta(l-4) linked JV-acetyl-D-glucosamine oligomer derivatives with wheat-germ agglutinin (lectin), FEBS Lett., 46 (1974) 224-228. 

Procedure. Suspend p-nitrophenyl 2-acetamido-2-deoxy-p-D-galactopyranoside (0.4 g, 1.17 mmol) and iV-acetyl-D-glucosamine (2.56 g, 11.57 mmol) in citrate-phosphate buffer (10 ml, 0.05 M, pH 4.5) in a round-bottomed flask. Heat this mixmre at 45-50 °C for 2-3 min and 30 °C for 5 min. Add p-JV-acetylhexosami-... 

Glucosamine 6-phosphate is obtained enzymically from hexose phosphate and glutamine and from glucosamine and ATP °. S)mthesis has been carried out by phosphorylation of i,3,4-tri-0-acetyl-iV-acetyl-/ D-glucosamine or JV-anisylidene-D-glucosamine and also by treating glucosamine with polyphosphoric acid. ... 

K. Sasaki, Y. Nishida, H. Uzawa, and K. Kobayashi, jV-Acetyl-6-sulfo-D-glucosamine as a promising mimic of iV-acetyl neuraminic acid, Bioorg. Med. Chem. Lett., 13 (2003) 2821-2823. 

Fig. 8 The receptor-binding domains of three TDAs, FimH [57], PapG-II [142], and F17a-G [143], viewed in the same orientation (obtained by superimpositioning of the structural core of their Ig-fold). The receptor binding sites are in complex with a-D-mannose, globotetraoside, and JV-acetyl glucosamine, respectively, shown as black ball-and-stick models. Structurally equivalent P-strands are labelled with their Ig-fold names...

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