Determination of the Anomeric Configuration of Sugar Residues in Acetylated Oligo- and Polysaccharides by Oxidation with Chromium Trioxide in Acetic Acid.

Hoffman, James S.; Lindberg, Bengt; Svensson, Sigfrid; Maron, Lajos; Sundbom, M.

doi:10.3891/acta.chem.scand.26-0661

Cited by 313 publications

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“…96 % of the glucosamine and 95 % of glucose residues, but no galactosamine or galactose residues remained intact. Therefore, glucosamine, glucuronic acid, and glucose possess the a-configuration and galactosamine and galacturonic acid have the P-configuration [19].…”

Section: Resultsmentioning

confidence: 99%

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The Cell Wall Polymer of the Extremely Halophilic Archaeon Natronococcus occultus

Niemetz

Kärcher

Kandler

et al. 1997

European Journal of Biochemistry

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The cell wall polymer of Nutronococcus occultus (DSM 3396) consists of L-glutamate, N-acetyl-Dglucosamine, N-acetyl-D-galactosamine, D-galacturonic acid, D-glucuronic acid and D-glucose in a molar ratio of 5:7:1:8:0.5:0.3.Partial acid hydrolysis of the cell wall polymer produced soluble fragments that could be separated by HPLC. A y-glutamyl dipeptide was isolated. In the intact cell wall polymer, the glutamate residues form a poly-(y-glutamine) chain with a length of about 60 monomers, which corresponds to a relative molecular mass of approximately 7700 Da. Two other soluble dimeric fragments, composed of glutamate and either glucosamine or galactosamine in a molar ratio of 1 : 1, were purified from the hydrolysate, suggesting the presence of two different oligosaccharides linked to the poly-(y-glutamine) chain of the intact polymer. The analysis of additional fragments, which were composed of an amino sugar and galacturonic acid or glucose indicated that one oligosaccharide consisted of a glucosamine pentamer in an a-1,3 linkage at the reducing end and an oligomer with at least five p-1,4-linked galacturonic acid residues at the non-reducing end. The second oligosaccharide was comprised of a galactosamine dimer in a b-1,3 liiikage at the reducing end and a maltose unit at the non-reducing end. Both oligosaccharides were linked to the a-amide group of the glutamine residues of the poly-(y-glutamine) chain. The whole cell wall polymer, which represents a novel type of natural glycoconjugate, has a relative molecular mass of 54 kDa.Keywords: cell wall; glycoconjugate; poly-(y-L-glutamine) ; Nutronococcus; Archaea.The archaeon Nutronococcus occultus survives optimally in extremely alkaline biotopes with a pH value between 9.5 and 10.0 and a salt concentration around 3.5 mol/l. The optimal temperature for growth is between 35°C and 40°C [I, 21. While living in this extreme habitat, the cell wall polymer not only has to protect the cells, but also has to facilitate the exchange of substrates with the environment. The chemical structure of the cell wall polymer of Hulococcus morrhuue has been elucidated [3], but no information is yet available on the structure of the cell wall polymers of alkaliphilic natronococci. The cell wall polymer of Nutronococcus occultus [4], which is described here, differs from all known archaeal cell wall structures such as pseudomurein, methanochondroitin, heterosaccharides, or S-layer (glyco-)proteins in its chemical composition and the mode of linkage of its oligosaccharides. MATERIALS AND METHODSOrganism and growth conditions. Nutronococcus occultus (DSM 3396) was grown in the medium described by Tindall [5], with minor modifications. The modified medium had the following composition (% mass/vol., all components analytical grade): casein hydrolysate (Oxoid) 0.5 ; yeast extract (Oxoid) 0.5; sodium glutamate, 0.5; NaCl, 20; KCl, 0.1; KH,PO,, 0.1; NH,Cl, 0.1 ; Na,CO,, 0.5; pH 9.5. In initial screening studies, N. occultus was grown in 1 1 conical flasks containing 250 ml medium, shaken at...

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Section: Resultsmentioning

confidence: 99%

“…The anomeric configuration of the sugars was determined by treatment with chromium trioxide [19]. Photolysis was used to determine the mode of linkage of glutamine-containing fragments (201.…”

Section: Methodsmentioning

confidence: 99%

The Cell Wall Polymer of the Extremely Halophilic Archaeon Natronococcus occultus

Niemetz

Kärcher

Kandler

et al. 1997

European Journal of Biochemistry

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“…Smith degradation and methylation analyses were performed as described in the literature (Goldstein et al, 1965;Hakomori, 1964;Hungerer et al, 1967;Lindberg et al, 1972;Reske & Jann, 1972 …”

Section: Methodsmentioning

confidence: 99%

Structural studies of an emulsion-stabilizing exopolysaccharide produced by an adhesive, hydrophobic Rhodococcus strain

Neu¹,

Dengler²,

Jann³

et al. 1992

Journal of General Microbiology

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The primary structure of an emulsion-stabilizing exopolysaccharide from the adhesive, hydrophobic Rhodococcus strain No. 33 was elucidated by NMR spectroscopy, methylation analyses, periodate oxidation and oligosaccharide analyses. The polysaccharide PS-33 consisted of rhamnose, galactose, glucose and glucuronic acid in molar ratios of 2: 1:l:l. The main chain contained 3-substituted &-D-g~UCUrOniC acid linked to the 3-position at a-L-rhamnose, in addition to 3-substituted residues of P-D-galactose and a-D-glucose. The a-L-rhamnose of the side chain was linked to position 4 of the galactose. In addition, the polysaccharide was 0-acetylated, corresponding to one acetyl group per repeating unit. From the results two structural possibilities could be suggested. As the polysaccharide carries hydrophobic groups (methyl of rhamnosel0-acetyl), it is very likely that these are of general significance for the emulsifying activity of polysaccharides. It also seems to be possible that this polysaccharide is at least partially responsible for the hydrophobic cell surface properties of the Rhodococcus strain No. 33 and it may be involved in hydrophobic interactions when adhering to hydrophobic interfaces.

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“…The product from the Smith degradation was carboxyl reduced, acetylated and treated with chromium trioxide in acetic acid (10,14). The P-linked sugar residues should be oxidized but not the a-linked residues.…”

Section: Acomentioning

confidence: 99%

Structural studies of the capsular polysaccharide from Streptococcus pneumoniae Type 12F

Leontein¹,

Lindberg²,

Lōnngren³

1981

Can. J. Chem.

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The capsular polysaccharide from Streptococcus pneumoniae type 12F is composed of D-glucosyl, D-galactosyl, 2-acetamido-2-deoxy-D-galactosyl, 2-acetamido-2,6-dideoxy-L-galactosyl, and 2-acetamido-2-deoxy-D-mannuronic acid residues in the proportions 2:1:1:1:1. The main structural evidence was adduced from nmr spectroscopy, methylation analysis, and specific degradations whereby it could be concluded that the polysaccharide is composed of hexasaccharide repeating-units having the structure:[Formula: see text]

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Determination of the Anomeric Configuration of Sugar Residues in Acetylated Oligo- and Polysaccharides by Oxidation with Chromium Trioxide in Acetic Acid.

Cited by 313 publications

References 0 publications

The Cell Wall Polymer of the Extremely Halophilic Archaeon Natronococcus occultus

The Cell Wall Polymer of the Extremely Halophilic Archaeon Natronococcus occultus

Structural studies of an emulsion-stabilizing exopolysaccharide produced by an adhesive, hydrophobic Rhodococcus strain

Structural studies of the capsular polysaccharide from Streptococcus pneumoniae Type 12F

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