Assignment of absolute configuration of sugars by g.l.c. of their acetylated glycosides formed from chiral alcohols

Leontein, Karin; Lindberg, Bengt; Lōnngren, Jörgen

doi:10.1016/s0008-6215(00)80882-4

Cited by 818 publications

(389 citation statements)

References 2 publications

Supporting

Mentioning

379

Contrasting

Unclassified

Order By: Relevance

“…The absolute configuration of the sugars was determined by gas-chromatography analysis of their acetylated (S)-2-octyl glycosides, while the absolute configuration of the amino acid residue was inferred by analyzing its butyl ester derivative. 35 All the samples were analyzed on an Agilent Technologies gas chromatograph 6850A equipped with a mass selective detector 5973N and a Zebron ZB-5 capillary column (Phenomenex, 30m x 0.25mm i.d., flow rate 1 mL/min, He as carrier gas). Acetylated methyl glycosides were analyzed accordingly with the following temperature program: 150 °C for 3 min, 150 °C240 °C at 3°C/min.…”

Section: Methodsmentioning

confidence: 99%

A Unique Capsular Polysaccharide Structure from the Psychrophilic Marine Bacterium Colwellia psychrerythraea 34H That Mimics Antifreeze (Glyco)proteins

et al. 2015

View full text Add to dashboard Cite

ABSTRACT:The low temperatures of polar regions and high altitude environments, especially icy habitats, present challenges for many microorganisms. Their ability to live under subfreezing conditions implies the production of compounds conferring cryotolerance. Colwellia psychrerythraea 34H, a -proteobacterium isolated from subzero Arctic marine sediments, provides a model for the study of life in cold environments. We report here the identification and detailed molecular primary and secondary structures of capsular polysaccharide from C. psychrerythraea 34H cells. The polymer was isolated in the water layer when cells were extracted by phenol/water and characterized by one-and two-dimensional NMR spectroscopy together with chemical analysis. Molecular mechanic and dynamic calculations were also performed. The polysaccharide consists of a tetrasaccharidic repeating unit containing two amino sugars and two uronic acids bearing threonine as substituent. The structural features of this unique polysaccharide resemble those present in antifreeze proteins and glycoproteins. These results suggest a possible correlation between the capsule structure and the ability of C. psychrerythraea to colonize subfreezing marine environments.

show abstract

Section: Methodsmentioning

confidence: 99%

A Unique Capsular Polysaccharide Structure from the Psychrophilic Marine Bacterium Colwellia psychrerythraea 34H That Mimics Antifreeze (Glyco)proteins

et al. 2015

View full text Add to dashboard Cite

show abstract

“…Uronic acids were analysed on a Biotronik LC-2000 sugar analyser at 60°C using a Dionex Aϫ8Ϫ11 anion-exchange resin and 0.02 M potassium phosphate, pH 2.4, as described [18]. The absolute configurations of the monosaccharides were determined by GLC of acetylated (S)-2-butyl (for GlcN and GalA) or (S)-2-octyl (for rhamnose, Rha) glycosides according to the published method [19,20] modified as described [21].…”

Section: Methodsmentioning

confidence: 99%

Structural and serological studies on a new acidic O‐specific polysaccharide of Proteus vulgaris O32

Shashkov

Babicka

Грачев

et al. 1998

European Journal of Biochemistry

View full text Add to dashboard Cite

The following structure of the O-specific polysaccharide chain (O-antigen) of the Proteus vulgaris O32 lipopolysaccharide (LPS) was established by 1 H-NMR and 13 C-NMR spectroscopy, including twodimensional NOESY and H-detected 1 H, 13 C heteronuclear multiple-quantum coherence (HMQC) experiments:In addition, an O-acetyl group was detected, which, most probably, is located at position 3 of a part of Rhap I residues. Serological studies, using rabbit polyclonal anti-(P. vulgaris O32) serum, homologous and heterologous Proteus O-antigens and related artificial antigens, revealed the importance of an A-D-GalA-associated epitope in manifesting the immunospecificity of P. vulgaris O32 and substantiated serological relationships between the O-antigen studied and those of some other Proteus strains.Keywords : Proteus vulgaris ; lipopolysaccharide; O-antigen; bacterial polysaccharide structure; serological specificity.Bacteria of the genus Proteus cause mainly wound and urinary tract infections, the latter sometimes leading to acute or chronic pyelonephritis and formation of bladder and kidney stones. Outer membrane lipopolysaccharide (LPS, endotoxin) is considered as a virulence factor of Proteus. Based on the Ospecific polysaccharide chains of LPS (O-antigens), two species, Proteus mirabilis and Proteus vulgaris, were classified into 60 O-serogroups [1, 2], and recently two more O-serogroups, O61 and O62, have been proposed for strains of the third species, Proteus penneri [3,4]. Chemical and immunochemical studies of Proteus LPS are important for understanding the molecular basis of the immunospecificity of Proteus strains and for their classification based on structural and serological data.A peculiar feature of the Proteus LPS is that in most Oserogroups the O-antigens are acidic due to the presence of phosphate groups, hexuronic acids, their amides with amino acids, sugar acetals with pyruvic acid or ethers with lactic acid ([3Ϫ9] and references cited therein). The role of acidic polysaccharides in the pathogenicity of Proteus and, particularly, in urinary tract infections was discussed [10]. The acidic character of Proteus polysaccharides enables bacteria to bind metal cations, Mg 2ϩ and Ca 2ϩ , via electrostatic interaction. This may enhance the formation of struvite and carbonate apatite stones in urinary tract under alkaline conditions in the presence of ammonia, one of the products of urea decomposition caused by Proteus bacteria [11]. Recently, the importance of an acidic polysaccharide rich in galacturonic acid and galactosamine was demonstrated for migration of P. mirabilis swarm cells by reduction of surface friction [12].A few structures of P. vulgaris O-antigens have been elucidated, some of them having been found neutral [7,13] and the others acidic [7Ϫ9]. Now, we report the structure of a new acidic O-specific polysaccharide of P. vulgaris O32 containing D-galacturonic acid. MATERIALS AND METHODSBacterial strains, growth, isolation and degradation of lipopolysaccharide. P. vulgaris O32 (strain PrK 57/...

show abstract

“…Neutral and acidic monosaccharides were identified by anion-exchange chromatography using a Biotronik LC-2000 sugar analyzer as described [11]. Absolute configurations of monosaccharides were determined after conversion into acetylated (S)-2-octyl or (S)-2-butyl glycosides [12,13] using GLC on a Hewlett-Packard 5890 chromatograph equipped with a glass capillary column (25 m× 0.2 mm) of Ultra 2 stationary phase. Similarly, L-lysine was identified by GLC after conversion into (S)-2-octyl ester by treatment of (S)-2-octanol in the presence of a drop of concentrated CF3CO2H at 130°C for 6 h followed by trifluoroacetylation.…”

Section: Chemical Methodsmentioning

confidence: 99%

Structures of new acidic O‐specific polysaccharides of the bacterium Proteus mirabilis serogroups O26 and O30

et al. 1996

View full text Add to dashboard Cite

show abstract

Assignment of absolute configuration of sugars by g.l.c. of their acetylated glycosides formed from chiral alcohols

Cited by 818 publications

References 2 publications

A Unique Capsular Polysaccharide Structure from the Psychrophilic Marine Bacterium Colwellia psychrerythraea 34H That Mimics Antifreeze (Glyco)proteins

A Unique Capsular Polysaccharide Structure from the Psychrophilic Marine Bacterium Colwellia psychrerythraea 34H That Mimics Antifreeze (Glyco)proteins

Structural and serological studies on a new acidic O‐specific polysaccharide of Proteus vulgaris O32

Structures of new acidic O‐specific polysaccharides of the bacterium Proteus mirabilis serogroups O26 and O30

Contact Info

Product

Resources

About