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Query: UNIPROT:P43026 (lipopolysaccharide)
 62,215 document(s) hit in 31,850,051 MEDLINE articles (0.00 seconds)

In the course of the organic synthesis of model compounds similar in some features to the lipid moiety of endotoxic lipopolysaccharide (LPS), Nacylated-D-glucosamine derivatives were prepared. One of these, N-palmitoyl-D-glucosamine, has been previously found to be mitogenic for athymic nude mouse B cells. This and other N-acylated homologs were tested for adjuvant activity in the immune response to human gamma-globulin (HGG) and sheep red blood cells (SRBC) in mice. Comparable or superior enhancement of the immune response was obtained for these glycolipids when compared to LPS in assays measuring anti-SRBC or HGG hemagglutinin titers. In the determination of hemolytic plaque formation, considerable adjuvant effect was shown by the lauroyl derivative, and less but still significant enhancement was achieved by the N-palmitoyl-D-glucosamine. In the rosette formation assay, in addition to the above two glycolipids, N-oleyl-D-glucosamine showed good adjuvant effect. In the latter two assays, the LPS was a superior adjuvant as compared to the synthetic glycolipids. The radiation protective effect of some of the better synthetic adjuvants was also investigated in mice. It was found that although LPS was more effective in this assay, the N-myristoyl-D-glucosamine and N-decanoyl-D-glucosamine compounds gave a definite protection, since up to 40% of the lethally irradiated (700 R) mice survived.
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PMID:Synthetic glycolipid adjuvants. 6 Apr 50

Lipid A isolated from lipopolysaccharide of Yersinia pseudotuberculosis was used for immunization of rabbits to afford antisera to lipid A with titers of 1:640 in the passive hemolysis test. Exhaustion of immune serume with sheep erythrocytes decreased antibody titers up to 1:160. Authentic samples of 2-(DL-3-hydroxytetradecanoyl)amino-2-deoxy-D-glucose 6-phosphate, 2-tetradecanoylamino-2-deoxy-D-glucose 6-phosphate and 2-acetamido-2-deoxy-D-glucose 6-phosphate have been synthesized in order to carry out a comparative study of inhibitory activity of these compounds and lipid A using a system of lipid A and antiserum to lipid A. As a result, the immunodominant moiety of the lipid A of Y. pseudotuberculosis proved to contain a D-glucosamine residue acylated with 3-hydroxytetradecanoic acid at the amino group. The nature of the fatty acid acylating the amino group of glucosamine does not play an important role in the structure of immunodominant moiety of lipid A.
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PMID:Structural studies on the immunodominant group of lipid A from lipopolysaccharide of Yersinia pseudotuberculosis. 8 32

The structure of lipopolysaccharide from a heptose-less mutant of Escherichia coli K-12 has been investigated. Lipopolysaccharide isolated from 32P-labeled cells was treated with mild alkali to yield two separable components: [OH-LPS]-I (approximately 70%) and [OH-LPS]-II (approximately 30%). Mild acidic treatment of [OH-LPS]-I gave mainly a product which was identified as (4-O-phosphoryl-N-beta-hydroxymyristyl-D-glucosaminyl)-beta(1 leads to 6)-N-beta-hydroxymyristyl-D-glucosamine 1-phosphate (Compound I). Further acidic hydrolysis of both [OH-LPS]-I and [OH-LPS]-II yielded as the main product (4-O-phosphoryl-N-beta-hydroxymyristyl-D-glucosaminyl)-beta(1 leads to 6)-N-beta-hydroxymyristyl-D-glucosamine (Compound II). The structures of the above products were deduced by a combination of compositional analyses, sensitivity to phosphomonoesterase, rates of hydrolysis of the phosphate groups and alkali-catalyzed beta elimination of the phosphate residues following appropriate oxidation of hydroxyl groups. These studies together with work reported in the accompanying papers have led to the identification of two species of lipopolysaccharide in the E. coli strain both of which contain a single glucosamine dissacharide unit but differ in having monosubstituted phosphate or pyrophosphate groups at the glycosidic position. Each species of lipopolysaccharide also appeared to be heterogeneous with respect to the number of esterified fatty acyl groups.
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PMID:Structure of the lipopolysaccharide from an Escherichia coli heptose-less mutant. I. Chemical degradations and identification of products. 22 86

Configurations were determined for previously identified amino components of the lipopolysaccharide from Pseudomonas aeruginosa N.C.T.C. 8505. Glucosamine and galactosamine belong to the D-series, and alanine and aminogalacturonic acid to the L-series. An additional amino component was identified as 2,4-diamino-2,4,6-trideoxy-D-glucose. This compound may be a characteristic component of the O-specific chain in lipopolysaccharides of strains of Pseudomonas aeruginosa belonging to Habs sero-group 3.
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PMID:Amino components of the lipopolysaccharide from Pseudomonas aeruginosa N.C.T.C. 8505. Presence of 2,4-diamino-2,4,6-trideoxy-D-glucose. 40 6

A lipopolysaccharide has been isolated from Pseudomonas maltophilia N.C.T.C. 10257. Monosaccharide components identified were L-rhamnose, 3-O-methyl-L-xylose, L-xylose, D-glucose, D-mannose, D-galacturonic acid, 2-amino-2-deoxy-galactose, 2-amino-2-deoxyglucose, and a 3-deoxy-2-octulosonic acid. Heptose was absent. In this and other respects, the lipopolysaccharide resembles the corresponding products from Xanthomonas species. Mild hydrolysis of the lipopolysaccharide with acid, followed by chromatography of the water-soluble products on Sephadex G-50, gave a polymeric, "side-chain" fraction containing rhamnose, 3-O-methylxylose, and xylose residues in the molar rations approximately 15:4:1. Methylation analysis, periodate oxidation, Smith degradation, and oxidation with chromium trioxide were the principal methods used in the study of this fraction. The following structure is proposed for the characteristic repeating-unit of the polymer.
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PMID:Lipopolysaccharides from Pseudomonas maltophilia: structural studies of the side-chain polysaccharide from strain N.C.T.C. 10257. 42 32

On hydrolysis, the purified lipopolysaccharide (LPS) isolated from Vibrio cholera, Inaba 569 B, yielded glucose, mannose, a heptose behaving like D-glycero-L-manno-heptose and one behaving like D-glycero-L-gluco-heptose, 2-amino-2-deoxyglucose, and glucuronic acid in the molar ratios of approximately 9:4:5:1:2:5. Studies on the LPS, the polysaccharide (PS), and carboxyl-reduced LPS showed that the PS has a branched structure, with (1 leads to 2)-linked mannopyranosyl and a heptopyranosyl, and (1 leads to 4)-linked glucopyranosyluronic and 2-amino-2-deoxyglucopyranosyl residues in the interior part of the molecule, and glucopyranosyl and heptopyranosyl residues as nonreducing end-groups.
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PMID:Structural investigations of the lipopolysaccharide isolated from Vibrio cholera, Inaba 569 B. 47 18

Lipid A was isolated from lipopolysaccharide of Yersinia pseudotuberculosis S form (strain 341, subtype IB) using mild hydrolysis with acetic acid. The purified material (yield about 25%, molecular weight about 2900) contained D-glucosamine (11%), fatty acids (54%), protein concomitant (9.7%) and phosphorus (approximately 2%). Dodecanoic and 3-hydroxy-tetradecanoic acids in a molar ratio of 1 : 3.6 were detected as major fatty acid constituents. The hydroxyl groups of D-glucosamine were acylated with the residues of both fatty acids, while the amino groups were substituted with the residue of 3-hydroxy-tetradecanoic acid. Such a simple fatty acid composition is reminiscent of that found in lipid A in Y. pestis.
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PMID:Studies on lipid A from Yersinia pseudotuberculosis lipopolysaccharide. Isolation and general characterization. 69 14

The lipopolysaccharide from Thiocapsa roseopersicina was isolated by phenol/water, being found in the water phase. It is cleaved into a polysaccharide moiety (degraded polysaccharide) and lipid A by hydrolysis with 10% acetic acid (100 degree C, 3 h). D-Mannose, L-rhamnose, 3-amino-3, 6-dideoxy-D-galactose and D-glucose are the major constituents of the degraded polysaccharide. 2-O-Methyl-L-rhamnose, 3-O-methyl-D-mannose, D-galactose, glucosamine and quinovosamine are minor constituents. D-Glycer-D-manno-heptose (tentatively identified) and 3-deoxy-D-manno-octulosonic acid were detected in only small amounts. Conspicuously, lipid A from T. roseopersicina contains a neutral sugar, D-mannose, in addition to D-glucosamine, as had been observed with lipid A from Chromatium vinosum D. Major fatty acids are beta-hydroxymyristic and lauric acids. Only trace amounts of phosphorus were found indicating this lipid A to be free of phosphate. The lipopolysaccharide of T. roseopersicina represents the O-antigen of the strain. It reacts with antisera prepared against living or heat-killed cells in passive hemagglutination.
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PMID:Isolation and characterization of the lipopolysaccharide of Thiocapsa roseopersicina. 71 Apr 28

The structure of the lipopolysaccharide from Escherichia coli K12, strain CR34 has been investigated. The lipopolysaccharide contains D-galactose, D-glucose, D-glucosamine, L-glycero D-mannoheptose, 2-keto-3-deoxyoctonate and lipid A. The core region does not contain D-glucosamine but contains galactose, glucose, and heptose in the molar ratios 1:3:6. Methylations were performed on the lipopolysaccharide and on the degraded polysaccharide obtained after acetic acid hydrolysis of the lipopolysaccharide. It was found that galactose is in terminal position partly in the form of galactopyranose, partly in the form of galactofuranose. A part of the heptose was found as unsubstituted heptofuranose. A mole of glucose was 1 leads to 2 linked and another mole of glucose was 1 leads to 6 linked. Periodate oxidation of the lipopolysaccharide followed by borohydride reduction eliminates galactose and only a part of glucose and of heptose. A mole of heptose gave mannose and thus it is unsubstituted in C6 and C7. One mole of glucose and one mole of heptose were not degraded by periodate oxidation.
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PMID:[Study of the lipopolysaccharide from Escherichia coli K12 CR34]. 77 Jan 68

The chemical structure of the lipid A component of lipopolysaccharides from Chromobacterium violaceum NCTC9694 was studied. Sequential treatment of lipopolysaccharide with alkali, acid, sodium borohydride and hydrazine allowed the isolation of a reduced glucosamine disaccharide. According to methylation studies and enzymic analysis with beta-N-acetylglucosaminidase the D-glucosamine residues are beta(1 leads to 6) linked. The disaccharide carries two phosphate groups, one being linked glycosidically, the other being linked as an ester to the non-reducing glucosamine. Application of a different degradation pathway shows that the ester-bound phosphate group is substituted by a 4-aminoarabinosyl residue and that the glycosidically linked phosphate group is substituted by a glucosaminyl residue. Neither the amino nor the hydroxyl groups of both these substituents are acylated. This backbone structure is shown in the following formula: (formula: see text). The amino groups of the central glucosamine disaccharide are substituted by D-3-hydroxy-dodecanoic acid, the hydroxyl groups by dodecanoic, L-2-hydroxydodecanoic and D-3-hydroxy-decanoic acid.
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PMID:The chemical structure of the lipid A component of lipopolysaccharides from Chromobacterium violaceum NCTC 9694. 86 18


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