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

Abstract

The discovery of the derivatives of 2,3‐diamino‐2,3‐dideoxyuronic acids and 5,7‐diamino‐3,5,7,9‐tetradeoxynonulosonic acids in bacterial polysaccharides enlarges the list of natural monosaccharides. Many of the new sugars carry unusual N‐substituents, such as formyl, (R)‐3‐hydroxybutyryl, and acetimidoyl groups. They are most characteristics of O‐chains of Pseudomonas aeruginosa lipopolysaccharides, composed almost exclusively of amino sugars or amphoteric amino sugars; the latter seem to play an important role as serological determinants. The identification of these sugars and the structural determination of the O‐specific polysaccharides provide the chemical basis for the classification of P. aeruginosa strains. Some of the new monosaccharides enter also the polysaccharides from some other bacteria.

Biosynthesis of UDP-GlcNAc(3NAc)A by WbpB, WbpE, and WbpD: Enzymes in the Wbp Pathway Responsible for O-Antigen Assembly in Pseudomonas aeruginosa PAO1

“…These distinctive molecules have primarily been identified in the complex cell wall matrices of pathogenic bacteria and the glycoproteins of certain archaea. To date, GlcNAc(3NAc)A has been detected in the LPS of a number of P. aeruginosa strains, including P1−III and P14, and the unique N -linked glycans of the methanogenic archaea Methanococcus voltae and Methanococcus maripalidus − . In addition to P. aeruginosa PAO1 (serotype O5), ManNAc(3NAc)A, the C2 epimer of GlcNAc(3NAc)A, is present in the LPS of other P. aeruginosa strains, as well as in the cell wall polysaccharide of the Gram-positive thermophile Bacillus stearothermophilus and the pathogens Bordatella pertussis , Bordatella parapertussis , and Bordatella bronchiseptica − .…”

Exploration of the Sialic Acid World

“…Over the years, a number of reviews about these nonulosonic acids have appeared. 114,595,[677][678][679][680][681] The first data about the occurrence of these "sialic acid-like" monosaccharides as components of lipopolysaccharides are from 1984 and reported by Knirel and coworkers at the N.D. Zelinsky Institute of Organic Chemistry, Moscow (Russia). 682 In view of the date of their first discovery, it may not be surprising that, in contrast to all the approaches used in the development of the sialic acid field, the analytical techniques had completely changed.…”

“…Survey of Reported Structures of Naturally Occurring 5,7-Diamino-3,5,7,9tetradeoxynon-2-ulosonic Acid Derivatives, and Some Related Structures, Which Are Terminal or Internal Units of Bacterial Homo-and Hetero-polysaccharides and Glycoprotein Glycans595,677,679,681 Name Abbreviation References…”