Arabinose 5- amino-5-deoxy

A monoaminopentose, 4-amino-4-deoxy-L-arabinose, is known as a component of some Gram-negative bacteria. It is linked, as the )5-pyranosyl phosphate (18), to a 2-amino-2-deoxy-y -D-glucopyranosyI residue in the lipid A part of the LPS. ... 

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>. 

N. catarrhalis,560 N. perflava,559 Moraxella duplex and Micrococcus calco-aceticus,443 and Escherichia coli,420 Vicari and Kabat,45 in studies of blood-group oligosaccharides, and Hellerqvist and colleagues,53 in an examination of the common core-polysaccharide of Salmonella typhimurium, have used similar methods. The examination of amino sugars as their peracetylated aminodeoxyalditols has also been used by Liideritz and colleagues72 to establish the occurrence of 4-amino-4-deoxy-L-arabinose in Salmonella lipopolysaccharides, and has been extended to aminodeoxyheptoses by Williams and Perry.561... 

AraNAc 4-acetamido-Ara 4-ace tamido-Xyl 3% ECNSS-M 190 occurrence in Salmonella of 4-amino-4-deoxy-L-arabinose 72... 

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. 

Amino-4-deoxy-L-arabinose had been previously found... 

The amino nitrile synthesis is particularly useful for the preparation of 2-amino-2-deoxy derivatives of rare sugars which would be difficult to obtain as intermediates in a synthesis involving animation alone. Thus, 2-amino-2-deoxy-L-glucose and 2-amino-2-deoxy-L-mannose can be prepared in good yield from the readily available L-arabinose.11,18... 

Baker s original work concerned the synthesis of 3-amino-3-deoxy-D-ribose, a component residue of the antibiotic puromycin.29 Two independent syntheses were achieved, starting from L-arabinose and D-xylose, respectively. The main steps in the reaction schemes are outlined in the following reaction sequences. 

Analogous reactions cleaved ethyl 2-acetamido-2-deoxy-l-thio-a-D-ga-lactofuranoside (ethyl 2-acetamido-2-deoxy-l-thio-D-g Z2/cero-/3-L-arabfno-hexofuranoside) to 2-amino-2-deoxy-/3-L-arabinose hydrochloride.88 ... 

In an extension of the work on the synthesis of IV-substituted amino sugars by the amino nitrile method, Kuhn and coworkers13 have prepared 2-(carboxymethylamino)-2-deoxy-D-glucose (2-deoxy-2-glycino-D-glucose), as the dipolar ion LXXXII, from glycine ethyl ester plus D-arabinose. 

Breazeale, S.D., Ribeiro, A.A., McClerren, A.L., Raetz, C.R.H. A formyltransferase required for polymyxin resistance in Escherichia coli and the modification of lipid A with 4-amino-4-deoxy-L-arabinose. Identification and function of UDP-4-deoxy-4-formamido-L-arabinose. J Biol Chem 280 (2005) 14154-14167. 

Zhou, Z., Ribeiro, A.A., Lin, S., Cotter, R.J., Miller, S.I., Raetz, C.R. Lipid A modifications in polymyxin-resistant Salmonella typhimurium PMRA-dependent 4-amino-4-deoxy-L-arabinose, and phosphoethanolamine incorporation. 1 Biol Chem 276 (2001) 43111—43121. 

Ara4 4-amino-4-deoxy-L-arabinose (also abbreviated as 4-aminoarabinose) CAMP cationic antimicrobial peptide Hep I heptose I Hep n heptose II... 

---