Deoxy from amino sugars

If the lactolhydroxyl group is substituted by NHj at C-atom i, one speaks of glycosylamines, or, by substitution with NHR, of iV-glycosides. Glyc-amines are i-amino-i-deoxy sugar alcohols. The nomenclature of the compounds found in nature, which are formed partly or entirely from amino sugars, is still not uniform. ... 

D-Clucuronic acid residues in heparin are linked as in disaccharide units 1 and 2, that is, either to 2-acetamido-2-deoxy-D-glucose ( Ana) or to 2-deoxy-2-sulfoamino (ANS) residues. (Although not apparent from Scheme 1, the amino sugar can be sulfated at C-6.)... 

What are the facts of life One of the most striking is that all known living systems involve the same types of polymers, i.e., three varieties of homochiral biopolymers. That is, each variety is composed of unique molecular building blocks having the same three-dimensional handedness. Thus, with rare exceptions, the proteins found in cells are composed exclusively of the 1-enantiomers of 19 optically active amino acids (Fig. 11.1). Similarly, only D-ribose and 2-deoxy-D-ribose sugars are found in the nucleic acid polymers that make up the RNAs and DNAs, which are essential for protein synthesis in the cell and for the transmission of genetic information from one generation to the next. 

Our interest in the synthesis of deoxy- and deoxy-amino sugars of the L-series originates from studies (1 ) on the products obtained by the action of fermenting baker s yeasts on such aromatic, a,/9-unsaturated aldehydes as cinnamaldehyde (la) and a-methylcinnamaldehyde (lb ). The transformation proceeds as indicated in Eq. 

Regioselective oxidation by brominolysis of dioxastannolane obtained from methyl / -L-ara-binopyranoside made it possible to accomplish (after subsequent oximation and reduction) a facile synthesis of 4-amino-4-deoxy-L-arabinose, an amino-sugar found in lipopolysaccharides of some Salmonella R. mutant strains <83CPB3778>. 

Uridine 5 -(2-acetamido-2-deoxy-a-n-gIucopyranosyluronic acid pyrophosphate) (36) was isolated from extracts of Achromobacter georgiopolitanum14Sa and Micrococcus lysodeikticus.149b The ester of uridine 5 -pyrophosphate with an unusual amino sugar, namely, a 2-acetamido-2,4,6-trideoxyhexose of unknown configuration, has... 

Piperidines are obtained from 5-amino-5-deoxy sugars by cycliza-tion with C-l their preparation therefore follows the general methods of preparation of such amino sugars. The 5-O-p-tolylsulfonyl- or 5-0-(methylsulfonyl)-pentoses constitute excellent starting-materials, as these sulfonyloxy groups can be replaced by azide, and the azides can be reduced to the 5-amino derivatives, which are capable of cyclization.240-251 The formation of piperidine 178 from 5-O-p-tolyI-sulfonyl-L-arabinose diethyl dithioacetal240 (176) and 177, and of 181 from benzyl 2,3-0-isopropylidene-5-0-(methylsulfonyl)-a-D-lyxofuranoside250 (179) and 180, are examples of this reaction sequence. 

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