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1. (Article ID: 5426)
Dworaczek K, Kurzylewska M, Karaś MA, Janczarek M, Pękala-Safińska A, Turska-Szewczuk A
A Unique Sugar l-Perosamine (4-Amino-4,6-dideoxy-l-mannose) Is a Compound Building Two O-Chain Polysaccharides in the Lipopolysaccharide of Aeromonas hydrophila Strain JCM 3968, Serogroup O6
Marine Drugs 17(5) (2019)
E254
Lipopolysaccharide (LPS) is the major glycolipid and virulence factor of Gram-negative bacteria, including Aeromonas spp. The O-specific polysaccharide (O-PS, O-chain, O-antigen), i.e., the surface-exposed part of LPS, which is a hetero- or homopolysaccharide, determines the serospecificity of bacterial strains. Here, chemical analyses, mass spectrometry, and 1H and 13C NMR spectroscopy techniques were employed to study the O-PS of Aeromonas hydrophila strain JCM 3968, serogroup O6. MALDI-TOF mass spectrometry revealed that the LPS of A. hydrophila JCM 3968 has a hexaacylated lipid A with conserved architecture of the backbone and a core oligosaccharide composed of Hep6Hex1HexN1HexNAc1Kdo1P1. To liberate the O-antigen, LPS was subjected to mild acid hydrolysis followed by gel-permeation-chromatography and revealed two O-polysaccharides that were found to contain a unique sugar 4-amino-4,6-dideoxy-l-mannose (N-acetyl-l-perosamine, l-Rhap4NAc), which may further determine the specificity of the serogroup. The first O-polysaccharide (O-PS1) was built up of trisaccharide repeating units composed of one α-d-GalpNAc and two α-l-Rhap4NAc residues, whereas the other one, O-PS2, is an α1→2 linked homopolymer of l-Rhap4NAc. The following structures of the O-polysaccharides were established: O-PS1 →3)-α-l-Rhap4NAc-(1→4)-α-d-GalpNAc-(1→3)-α-l-Rhap4NAc-(1→, O-PS2 →2)-α-l-Rhap4NAc-(1→. The present paper is the first work that reveals the occurrence of perosamine in the l-configuration as a component of bacterial O-chain polysaccharides.
O-antigen, NMR spectroscopy, O-polysaccharide, endotoxin, structure elucidation, lipopolysaccharide (LPS), MALDI-TOF mass spectrometry, Aeromonas hydrophila, L-perosamine, l-Rha4NAc
NCBI PubMed ID: 31035397Publication DOI: 10.3390/md17050254Journal NLM ID: 101213729Publisher: Basel, Switzerland: Molecular Diversity Preservation International
Correspondence: aturska

hektor.umcs.lublin.pl
Institutions: Department of Genetics and Microbiology, Maria Curie-Skłodowska University in Lublin, Akademicka 19, Lublin 20-033, Poland, Department of Fish Diseases, National Veterinary Research Institute, Partyzantów 57, Puławy 24-100, Poland
Methods: 13C NMR, 1H NMR, methylation, GLC-MS, NMR-2D, SDS-PAGE, sugar analysis, GLC, MALDI-TOF MS, GPC
The publication contains the following compound(s):
- Compound ID: 13649
Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide
Reference(s) to other database(s): GTC:G32007NJ
- Compound ID: 13650
Structure type: homopolymer
Compound class: O-polysaccharide, O-antigen
Reference(s) to other database(s): GTC:G14918BB
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2. (Article ID: 6283)
Nguyen JM, Evans CS, Wright NM, Townsend SD
Synthesis of the Aeromonas veronii strain Bs8 disaccharide repeating unit
Carbohydrate Research 514 (2022)
108530
Presented herein is the synthesis of the Aeromonas veronii disaccharide repeating unit which has been achieved in 11 steps starting from D-fucose and D-galactosamine.
synthesis, Gram-negative, fucose, glycosylation, GalNAc
NCBI PubMed ID: 35263695Publication DOI: 10.1016/j.carres.2022.108530Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: S.D. Townsend
vanderbilt.edu>
Institutions: Department of Chemistry, Vanderbilt University, Nashville, TN, 37235, United States
Methods: 13C NMR, 1H NMR, NMR-2D, IR, TLC, chemical synthesis, glycosylation, optical rotation measurement, SEC, HR-ESI-MS
The publication contains the following compound(s):
- Compound ID: 13649
Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide
Reference(s) to other database(s): GTC:G32007NJ
- Compound ID: 13651
Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide, O-antigen
Reference(s) to other database(s): GTC:G00005IV
- Compound ID: 16220
Structure type: oligomer
; 496.1794 [M+Na]+
C21H31NO11
Aglycon: p-methoxyphenyl
Compound class: O-polysaccharide
- Compound ID: 12219
Structure type: polymer chemical repeating unit
Compound class: O-polysaccharide
Reference(s) to other database(s): GTC:G91036FH
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