Die Konstitution der Lacto‐<i>N</i>‐biose I

Kühn, Richard; Baer, Hans H.; Gauhe, Adeline

doi:10.1002/cber.19540871026

Cited by 73 publications

(32 citation statements)

References 29 publications

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“…The chromogen formed by fraction -5 therefore is substituted. These findings favour a 1,6 linkage between the two glucosamine residues of fraction -5 , since a corresponding 1,l or 1,4 linked disaccharide would not react in the Morgan-Elson reaction, while a 1,3 linked disaccharide would yield free chromogen ( R G~~N A~ = 1.64) and a color yield between I00 and 200 O l 0 [45,46].…”

Section: 'mentioning

confidence: 84%

Biochemical Studies on Lipopolysaccharides of Salmonella R Mutants

Gmeiner

Lüderitz

Westphal

1969

European Journal of Biochemistry

166

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The endotoxically active cell wall glycolipid of a highly deficient heptose-less R mutant of Salmonella minnesota, consisting of 2-keto-3-deoxyoctonic acid (KDO) and lipid A, was subjected to hydrazinolysis. Besides fatty acid hydrazides, a water-soluble main fraction was obtained, containing KDO, glucosamine, and ester phosphate and free phosphorylethanolamine. The application of two procedures of partial hydrolysis, followed by paper electrophoretic separation, led to seven oligosaccharides.Their structures were evaluated with the aid of the following analytical methods: further acid degradation, borohydride reduction, ninhydrin degradation, the Morgan-Elson reaction, treatment with phosphomonoesterase and N-acetylglucosaminidases. The results show that the backbone of lipid A contains phosphorylated glucosaminyl-tglucosamine disaccacharide units, probably linked /3-1,6, to which a trisaccharide composed of three KDO rehidues is linked ketosidically to form a pentasaccharide which appears to be a common structure in many Enterobacteriaceae.

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Section: 'mentioning

confidence: 84%

Biochemical Studies on Lipopolysaccharides of Salmonella R Mutants

Gmeiner

Lüderitz

Westphal

1969

European Journal of Biochemistry

166

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“…After treatment of lipoteichoic acid with H F for 120 h, oligosaccharide I1 was completely converted into oligosaccharide 111, the total ribitol was liberated and the reactivity of hexosamine in the Elson-Morgan reaction approached 50%. These results suggest that a 3-or 6-substituted N-acetylgalactosamine residue [54] forms the reducing terminus of oligosaccharide 111 and is in oligosaccha- ride I1 linked to the ribitol moiety through a particularly acidlabile j-glycosidic bond [6]. The oligosaccharide mixture in the 36-h hydrolysate was treated with NaBH,.…”

Section: The Structure Of the Phosphate-free Repeating Unitmentioning

confidence: 94%

The structure of pneumococcal lipoteichoic acid

Behr

Fischer

Peter‐Katalinić

et al. 1992

European Journal of Biochemistry

128

104

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Pneumococcal lipoteichoic acid was extracted and purified by a novel, quick and effective procedure. Structural analysis included methylation, periodate oxidation, Smith degradation, oxidation with Cr03, and fast-atom-bombardment mass spectrometry. Hydrolysis with 48% (by mass) HF and subsequent phase partition yielded the lipid anchor (I), the dephosphorylated repeating unit of the chain (11) and a cleavage product of the latter (111). The proposed structures are:where AATGal is 2-acetamido-4-amino-2,4,6-trideoxygalactose, and all sugars are in the pyranose form and belong to the D-series.Alkaline phosphodiester cleavage of lipoteichoic acid, followed by treatment with phosphomonoesterase, resulted in the formation of I1 and IV, with IV as the prevailing species:The linkage between the repeating units was established as phosphodiester bond between ribitol 5-phosphate and position 6 of the glucosyl residue of adjacent units. The chain was shown to be linked to the lipid anchor by a phosphodiester between its ribitol 5-phosphate terminus and position 6 of the non-reducing glucosyl terminus of I. The lipoteichoic acid is polydisperse: the chain length may vary between 2 and 8 repeating units and variations were also observed for the fatty acid composition of the diacylglycerol moiety. Preliminary results suggest that repeating units I1 and IV are enriched in separate molecular species. All species were associated with Forssman antigenicity, albeit to a various extent when related to the non-phosphocholine phosphorus. Owing to its unique structure, the described macroamphiphile may be classified as atypical lipoteichoic acid. 6In 1943 pneumococcal Forssman antigen was identified by Goebel et al. as the first 'lipocarbohydrate' among Grampositive bacteria [l]. On the basis of its amphiphilic nature effected by covalently attached fatty acids [ 1,2] and its association with the plasma membrane, it was later classified as a choline-containing lipoteichoic acid [3]. The presence of glucose, N-acetylgalactosamine, ribitol, phosphorus, and choline led to the speculation that lipoteichoic acid might be Correspondence to W. Fischer, Institut fur Biochemie der Med.Fak., Univ. Erlangen-Nurnberg, Fahrstrasse 17, W-8520 Erlangen, Federal Republic of Germany Abbreviations. AATCal, 2-acetamido-4-amino-2,4,6-trideoxy-~-galactose; Cho, choline; Gro, glycerol; abbreviations of fatty acids are illustrated by the following examples: 18 :0, octadecanoic acid; 9 -18 : 1, octadecenoic acid with the double bond at position 9 (oleic acid).Note. This work was carried out in partial fulfillment of the requirements for an MD degree from the University ErlangenNurnberg, 1992, for T. Behr. structurally related to pneumococcal C polysaccharide, the homologous wall teichoic acid [l -41. However, except for two notes that the fatty acids comprise 6% (by mass) Although serological studies showed cross reactivity between teichoic acid and lipoteichoic acid [7, 81, lipoteichoic acid is the unique carrier of Forssman antigenicity, eliciting antibody ...

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“…269, 33 %). Kuhn, Gauhe & Baer (1954) report that 4-0-derivatives of N-acetylhexosamines fail to give a positive Morgan & Elson (1934) reaction and because the N-acetylated muramic acid derivative gave a positive reaction it seemed likely that the substituent group was on C-3. A structure in agreement with the analyses and reactions described was 3-0-oa-carboxyethylhexosamine, but this had mol.wt.…”

Section: Resultsmentioning

confidence: 99%

The isolation, characterization, and chemical synthesis of muramic acid

1959

Microchemical Journal

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Die Konstitution der Lacto‐N‐biose I

Cited by 73 publications

References 29 publications

Biochemical Studies on Lipopolysaccharides of Salmonella R Mutants

Biochemical Studies on Lipopolysaccharides of Salmonella R Mutants

The structure of pneumococcal lipoteichoic acid

The isolation, characterization, and chemical synthesis of muramic acid

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