Aldoses 4- acetamido-4-deoxy

The results of inhibition studies with aldonolactones and 5-amino-5-deoxyaldonolactams may be summarized as follows y -D-glycosidases are inhibited by 1,5-lactones and the lactams some 100- to > 10,000-fold better than by the parent aldoses, with Kj values from 200 //Mto <0.1 nM. Al-dono-1,4-lactones are probably no better inhibitors than aldoses or polyols of comparable structure, with the possible exception s of 2-acetamido-2-deoxy-D-glucono-1,4-lactone. 

Aldoses containing acetamido-, amino-, deoxy-, and thio-groups have been examined by g.l.c. of their peracetylated aldononitrile derivatives. Chemical... 

An improved synthesis of the oximino-lactone derivative 63 ( PUGNAc ) in five steps from 2-acetamido-2-deoxy-a-D-glucopyranose tetraacetate has been described, the critical step being a low temperature oxidation of an acyclic aldose oxime intermediate to a cyclic oximino-lactone with NCS and DBU. " The D-xylono-l,5-lacatam oxime derivative 64 has been synthesized from an L-serinal derivative as a potential A-acetylglucosaminyl transferase inhibitor. ... 

Scheme 54. Partial fragmentation of 3-acetamido-3-deoxy and 3-acetamido-3,6-dideoxy aldose diethyl dithioacetals.

Scheme 55. Partial fragmentation of a 3-acetamido-3-deoxy aldose diethyl dithioacetal showing fragment A.

P-D-2-Acetamido-2-deoxy-hexosidase Acetylcholinesterase Adenosine 3, 5 -phosphate phosphodiesterase Aldose-ketose isomerases (general)... 

Amino-Alditols. - Aldose oximes, e.p... of mannose and arabinose, can be reduced electrochemically to 1-aminoalditols glucose oxime reacted differently, because, it is proposed, of its strong tendency to cyclize to an N-glucosyl hydroxylamine derivative. l-Amino-2-acetamido-1,2-dideoxy-D-alditols have been prepared by sodium cyano-borohydride reduction of 2-acetamido-2-deoxy-glycosylamines (D-Glc, D-Man, and D- lc-D-Glc).6-(5-deoxy-D-ribit-5-yl)amino-uracil has been condensed with 2-chloro-4-hydroxybenzaldehyde to give a flavin derivative which was further elaborated to Redox Coenzyme Factor 420. ... 

A large number of aldoses and derivatives have been tested as substrates for NeuSAc aldolase which adds pyruvic acid to the aldose. A free hydroxyl group is required at C-3 of the aldose, and aldoses with the -configuration at C-3 lead to products with the iS-configuration at C-4 in the product. An enzymic method for the conversion of /V-acetyl-D-mannosamine and D-mannose into neuraminic acid and Kdo respectively has been improved and simplified, and the reactions were carried out on a 10 g scale. iV-Acetyl-4-azido-4-deoxy-D-mannosaniine has been converted with an aldolase into 5-acetamido-7-azido-3,5,7-trideoxy-D-g/ycero-D-gfl/flcro-2-nonulopyranosonicacid. ... 

AUylation of unprotected aldoses in aqueous media has previously been carried out with allyl bromide and tin (see Vol. 25, Chapter 2, Ref. 31). This method has now been improved by replacement of tin with indium, and extended to substituted allylic Inomides. Its usefiilness is impressively demonstrated by the conversion of 2-acetamido-2-deoxy-D-inannose to neuraminic add derivative 42 in 3 steps and 45% overall yield, as shown in Scheme 7. ... 

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