2,3-diamino-2,3-dideoxy-d-glucofuranurono-6,3-lactam from the hydrolysate of Pseudomonas aeruginosa P14 lipopolysaccharide

Abstract

An unknown amino sugar, U-7, which had been detected in the hydrolysate of the polysaccharide fraction (F-A) of Pseudomonas aeruginosa P14 lipopolysaccharide, was isolated from the hydrolysate of whole cells of this micro-organism and converted into the N-acetyl derivative (U-7NAc). On the basis of i.r.-absorption spectrometry, 13C-n.m.r. and 1H-n.m.r. spectroscopy and mass spectrometry, the structure of compound U-7NAc was identified as 2-acetamido-3-amino-2,3-dideoxyhexofuranurono-6,3-lactam. The configuration of compound U-7NAc was then unequivocally identified as 2-acetamido-3-amino-2,3-dideoxy-D-glucofuranurono-6,3-lactam by comparing the synthetic and natural compounds. Compound U-7 and synthetic 2,3-diamino-2,3-dideoxy-D-glucofuranurono-6,3-lactam showed the same behaviour on chromatography. G.l.c.--mass-spectral analyses of fraction F-A and synthetic 2,3-diacetamido-2,3-dideoxy-D-glucuronic acid after methanolyses and trimethylsilylations showed the presence of the same derivative. It was concluded that the amino sugar U-7 was produced from the 2,3-diacetamido-2,3-dideoxy-D-glucuronic acid residue present in fraction F-A.

Distribution of 2,3-Diaminohexuronic Acid in Strains of Propionibacterium and Other Bacteria

“…As noted a b o v e , v a r i o u s o t h e r 2,3-diamino-2,3-dideoxyhexuronic acids have been identified by I3C nuclear magnetic resonance spectroscopy in the polysaccharides of Pseudornonas aeruginosa (7,(10)(11)(12)(13)16) and may well occur in the polysaccharides of other organisms as well.…”

“…At the time that 2,3-diamino-2,3-dideoxyhexuronic acid was first isolated and identified in the cell wall polysaccharide of Propionibacterium acnes (6), I was not aware that an apparently identical substance had been described by Knirel et al (10) (16,17). In the present investigations five strains of Pseudomonas aeruginosa were examined, four of them as TCA extracts of whole cells and one as lipopolysaccharide.…”

2,3-Diamino-2,3-dideoxyuronic and 5,7-diamino-3,5,7,9-tetradeoxynonulosonic acids: new components of bacterial polysaccharides

“…Of the sugars of the class considered, only 2,3-diamino-2,3-dideoxy-D-glucuronic acid has been released on acid hydrolysis of the corresponding polysaccharides [9,10,14]. It easily forms 6,3-furanolactam 15 under the conditions of hydrolysis.…”

“…Sugar 1 is also a constituent of the LPS of P. aeruginosa P14 and some other strains belonging to Habs-serotypes 1 and 12 [9,10]. The structures of their polysaccharides have not been established, however, it seems to be 6 for the Habs-serotype 1, which is serologically identical with the 06serogroup *…”

Isolation and identification of uridine(5′)-diphospho(1)-2,3-diacetamido-2,3-dideoxy-α-d-glucopyra nuronic acid from Pseudomonas aeruginosa P1-III

“…A new type of aminouronic acids, 2,3-diacetamido-2,3-dideoxy-D-glucuronic acid [3,4], 2,3-diacetamido-2,3dideoxy-D-mannuronic acid [5] and 2,3-diacetamido-2,3-dideoxy-L-guluronic acid [6], has been found to be a constituent of the 0-specific polysaccharides of some Ps. aeruginosa lipopolysaccharides.…”