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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

1
Department of Genetics and Microbiology, Maria Curie-Skłodowska University in Lublin, Akademicka 19, Lublin 20-033, Poland
2
Department of Fish Diseases, National Veterinary Research Institute, Partyzantów 57, Puławy 24-100, Poland
*
Author to whom correspondence should be addressed.
Mar. Drugs 2019, 17(5), 254; https://doi.org/10.3390/md17050254
Received: 9 April 2019 / Revised: 20 April 2019 / Accepted: 23 April 2019 / Published: 28 April 2019
(This article belongs to the Special Issue Marine Bacterial Toxins)
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Abstract

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. View Full-Text
Keywords: Aeromonas hydrophila; lipopolysaccharide (LPS); endotoxin; structure elucidation; O-antigen; O-polysaccharide; l-perosamine; l-Rha4NAc; NMR spectroscopy; MALDI-TOF mass spectrometry Aeromonas hydrophila; lipopolysaccharide (LPS); endotoxin; structure elucidation; O-antigen; O-polysaccharide; l-perosamine; l-Rha4NAc; NMR spectroscopy; MALDI-TOF mass spectrometry
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited (CC BY 4.0).
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Dworaczek, K.; Kurzylewska, M.; Karaś, M.A.; 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. Mar. Drugs 2019, 17, 254.

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