Found 8 structures.
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1. Compound ID: 5756
Structure type: oligomer
Trivial name: MGlcDAG, glycoglycerolipid, glycosylglycerolipid
Compound class: glycolipid, glycoglycerolipid
Contained glycoepitopes: IEDB_142488,IEDB_144998,IEDB_146664,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 2512
Nakano M, Fischer W "The glycolipids of Lactobacillus casei DSM 20021" -
Hoppe-Seyler's Zeitschrift fur Physiologische Chemie [German] 358 (1977) 1439-1453
Journal NLM ID: 2985060RPublisher: Berlin: Walter De Gruyter
Methods: EI-MS
- Article ID: 4175
Demel R, Lindblom G, Rilfors L "Packing of a triacylglucolipid from the membrane of Acholeplasma laidlawii strain A at the air/water interface" -
Biochimica et Biophysica Acta 1190 (1994) 416-420
Pressure-area curves were generated at 22 degrees C and 40 degrees C for three glucolipids isolated from Acholeplasma laidlawii strain A-EF22. The glucolipids are 1,2-diacyl-3-O-(α-D-glucopyranosyl)-sn-glycerol (MGlcDAG), 1,2-diacyl-3-O-[α-D-glucopyranosyl-(1→2)-O-α-D-glucopyranosyl]-sn-glycerol (DGlcDAG), and 1,2-diacyl-3-O-[3-O-acyl-(α-D-glucopyranosyl)]-sn-glycerol (MAMGlc-DAG). The curves for MGlcDAG and DGlcDAG are characteristic for monolayers in a liquid phase at both temperatures. MGlcDAG has a smaller molecular area at all surface pressures compared to DGlcDAG. At 22 degrees C MAMGlcDAG shows a phase transition at 13 mN/m. However, at 40 degrees C the pressure-area curve for this lipid is characteristic for a monolayer in a liquid state. Mixed MAMGlcDAG-DGlcDAG and MGlcDAG-DGlcDAG monolayers showed no significant deviation from the additivity rule at 40 degrees C. The area per acyl chain is nearly the same for MAMGlcDAG and MGlcDAG. Our study supports our previous results that aqueous dispersions of these lipids form non-lamellar, reversed aggregates.
NCBI PubMed ID: 8142444Publication DOI: 10.1016/0005-2736(94)90102-3Journal NLM ID: 0217513Publisher: Elsevier
Institutions: Department of Biochemistry of Membranes, University of Utrecht, Utrecht, The Netherlands
Methods: monolayer technique
- Article ID: 4210
Huang Y, Anderson R "Glucosyl diglyceride lipid structures in Deinococcus radiodurans" -
Journal of Bacteriology 177 (1995) 2567-2571
The structures of two lipids from the radiation-resistant bacterium Deinococcus radiodurans are reported here: 1,2-diacyl-3-α-glucopyranosyl-glycerol and 3-O-[6'-O-(1",2"-diacyl- 3"-phosphoglycerol)-α-glucopyranosyl]-1,2-diacylglycerol. These lipids are strikingly different from previously characterized polar lipids from this organism, in that they are not unique to the genus Deinococcus and indeed have counterparts in both gram-negative and gram-positive bacteria. Moreover, as examples of glucose-containing lipids, they further illustrate the diversity of carbohydrate-containing lipids in D. radiodurans, from which lipids containing galactose and N-acetylglucosamine have already been structurally characterized.
NCBI PubMed ID: 7730293Journal NLM ID: 2985120RPublisher: American Society for Microbiology
Institutions: Department of Microbiology and Infectious Diseases, University of Calgary, Alberta, Canada
Methods: 13C NMR, 1H NMR
- Article ID: 6060
Gisch N, Peters K, Thomsen S, Vollmer W, Schwudke D, Denapaite D "Commensal Streptococcus mitis produces two different lipoteichoic acids of type I and type IV" -
Glycobiology 31(12) (2021) 1655-1669
The opportunistic pathogen Streptococcus mitis possesses, like other members of the Mitis group of viridans streptococci, phosphorylcholine (P-Cho)-containing teichoic acids (TAs) in its cell wall. Bioinformatic analyses predicted the presence of TAs that are almost identical with those identified in the pathogen Streptococcus pneumoniae, but a detailed analysis of S. mitis lipoteichoic acid (LTA) was not performed to date. Here, we determined the structures of LTA from two S. mitis strains, the high-level beta-lactam and multiple antibiotic resistant strain B6 and the penicillin-sensitive strain NCTC10712. In agreement with bioinformatic predictions, we found that the structure of one LTA (type IV) was like pneumococcal LTA, except the exchange of a glucose moiety with a galactose within the repeating units. Further genome comparisons suggested that the majority of S. mitis strains should contain the same type IV LTA as S. pneumoniae, providing a more complete understanding of the biosynthesis of these P-Cho-containing TAs in members of the Mitis group of streptococci. Remarkably, we observed besides type IV LTA, an additional polymer belonging to LTA type I in both investigated S. mitis strains. This LTA consists of β-galactofuranosyl-(1,3)-diacylglycerol as glycolipid anchor and a poly-glycerol-phosphate chain at the O-6 position of the furanosidic galactose. Hence, these bacteria are capable of synthesizing two different LTA polymers, most likely produced by distinct biosynthesis pathways. Our bioinformatics analysis revealed the prevalence of the LTA synthase LtaS, most probably responsible for the second LTA version (type I), among S. mitis and Streptococcus pseudopneumoniae strains.
lipoteichoic acid, nuclear magnetic resonance (NMR), mass spectrometry (MS), glycosylglycerolipids, Streptococcus mitis
NCBI PubMed ID: 34314482Publication DOI: 10.1093/glycob/cwab079Journal NLM ID: 9104124Publisher: IRL Press at Oxford University Press
Correspondence: ngisch@fz-borstel.de
Institutions: Division of Bioanalytical Chemistry, Priority Area Infections, Research Center Borstel, Leibniz-Center for Medicine and Biosciences, Parkallee 1-40, 23845 Borstel, Germany, Department of Microbiology, University of Kaiserslautern, Paul-Ehrlich Stra?e 24, 67663 Kaiserslautern, Germany, Division of Bioanalytical Chemistry, Research Center Borstel, Leibniz Lung Center, Borstel, Germany
Methods: 13C NMR, 1H NMR, NMR-2D, 31P NMR, de-O-acylation with hydrazine, composition analysis, extraction, HPTLC, bioinformatic analysis, HR-MS
- Article ID: 6087
Knaack W, Holzl G, Gisch N "Structural Analysis of Glycosylglycerolipids Using NMR Spectroscopy" -
Methods in Molecular Biology 2295 (2021) 249-272
Glycosylglycerolipids are essential components of plant and bacterial membranes. These lipids exert central roles in physiological processes such as photosynthesis in plants or to maintain membrane stability in bacteria. They are composed of a glycerol backbone esterified with two fatty acids at the sn-1 and sn-2 positions, and carbohydrate moieties connected via a glycosidic bond at the sn-3 position. Nuclear magnetic resonance (NMR) spectroscopy is a state-of-the-art technique to determine the nature of the bound carbohydrates as well as their anomeric configurations. Here we describe the analysis of intact glycosylglycerolipids by NMR spectroscopy to determine structural details of their sugar head groups without the need of chemical derivatization.
carbohydrates, NMR spectroscopy, fatty acids, anomeric configuration, glycosylglycerolipids, galactolipid
NCBI PubMed ID: 34047981Publication DOI: 10.1007/978-1-0716-1362-7_14Journal NLM ID: 9214969Publisher: Springer
Correspondence: ngisch@fz-borstel.de
Institutions: Division of Bioanalytical Chemistry, Research Center Borstel, Leibniz Lung Center, Borstel, Germany, Institute of Molecular Physiology and Biotechnology of Plants (IMBIO), University of Bonn, Bonn, Germany
Methods: 13C NMR, 1H NMR, NMR-2D, extraction, HPTLC
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2. Compound ID: 10044
Structure type: oligomer
Trivial name: diglucosyldiacylglycerol, DGlcDAG
Compound class: glycolipid
Contained glycoepitopes: IEDB_142488,IEDB_144998,IEDB_146664,IEDB_161523,IEDB_232584,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 4175
Demel R, Lindblom G, Rilfors L "Packing of a triacylglucolipid from the membrane of Acholeplasma laidlawii strain A at the air/water interface" -
Biochimica et Biophysica Acta 1190 (1994) 416-420
Pressure-area curves were generated at 22 degrees C and 40 degrees C for three glucolipids isolated from Acholeplasma laidlawii strain A-EF22. The glucolipids are 1,2-diacyl-3-O-(α-D-glucopyranosyl)-sn-glycerol (MGlcDAG), 1,2-diacyl-3-O-[α-D-glucopyranosyl-(1→2)-O-α-D-glucopyranosyl]-sn-glycerol (DGlcDAG), and 1,2-diacyl-3-O-[3-O-acyl-(α-D-glucopyranosyl)]-sn-glycerol (MAMGlc-DAG). The curves for MGlcDAG and DGlcDAG are characteristic for monolayers in a liquid phase at both temperatures. MGlcDAG has a smaller molecular area at all surface pressures compared to DGlcDAG. At 22 degrees C MAMGlcDAG shows a phase transition at 13 mN/m. However, at 40 degrees C the pressure-area curve for this lipid is characteristic for a monolayer in a liquid state. Mixed MAMGlcDAG-DGlcDAG and MGlcDAG-DGlcDAG monolayers showed no significant deviation from the additivity rule at 40 degrees C. The area per acyl chain is nearly the same for MAMGlcDAG and MGlcDAG. Our study supports our previous results that aqueous dispersions of these lipids form non-lamellar, reversed aggregates.
NCBI PubMed ID: 8142444Publication DOI: 10.1016/0005-2736(94)90102-3Journal NLM ID: 0217513Publisher: Elsevier
Institutions: Department of Biochemistry of Membranes, University of Utrecht, Utrecht, The Netherlands
Methods: monolayer technique
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3. Compound ID: 10045
Structure type: oligomer
Trivial name: MAMGlc-DAG
Compound class: glycolipid
Contained glycoepitopes: IEDB_142488,IEDB_144998,IEDB_146664,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 4175
Demel R, Lindblom G, Rilfors L "Packing of a triacylglucolipid from the membrane of Acholeplasma laidlawii strain A at the air/water interface" -
Biochimica et Biophysica Acta 1190 (1994) 416-420
Pressure-area curves were generated at 22 degrees C and 40 degrees C for three glucolipids isolated from Acholeplasma laidlawii strain A-EF22. The glucolipids are 1,2-diacyl-3-O-(α-D-glucopyranosyl)-sn-glycerol (MGlcDAG), 1,2-diacyl-3-O-[α-D-glucopyranosyl-(1→2)-O-α-D-glucopyranosyl]-sn-glycerol (DGlcDAG), and 1,2-diacyl-3-O-[3-O-acyl-(α-D-glucopyranosyl)]-sn-glycerol (MAMGlc-DAG). The curves for MGlcDAG and DGlcDAG are characteristic for monolayers in a liquid phase at both temperatures. MGlcDAG has a smaller molecular area at all surface pressures compared to DGlcDAG. At 22 degrees C MAMGlcDAG shows a phase transition at 13 mN/m. However, at 40 degrees C the pressure-area curve for this lipid is characteristic for a monolayer in a liquid state. Mixed MAMGlcDAG-DGlcDAG and MGlcDAG-DGlcDAG monolayers showed no significant deviation from the additivity rule at 40 degrees C. The area per acyl chain is nearly the same for MAMGlcDAG and MGlcDAG. Our study supports our previous results that aqueous dispersions of these lipids form non-lamellar, reversed aggregates.
NCBI PubMed ID: 8142444Publication DOI: 10.1016/0005-2736(94)90102-3Journal NLM ID: 0217513Publisher: Elsevier
Institutions: Department of Biochemistry of Membranes, University of Utrecht, Utrecht, The Netherlands
Methods: monolayer technique
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4. Compound ID: 10061
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LIP-(1-1)-+
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Gro-(3--P--6)--a-D-Glcp-(1-2)-a-D-Glcp-(1-3)-Gro
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LIP-(1-2)-+ |
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Structure type: oligomer
Trivial name: glycerophosphoglycolipid
Contained glycoepitopes: IEDB_142488,IEDB_144998,IEDB_144999,IEDB_146664,IEDB_161523,IEDB_232584,IEDB_241118,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 4186
Hauksson JB, Lindblom G, Rilfors L "Structures of glucolipids from the membrane of Acholeplasma laidlawii strain A-EF22. I. Glycerophosphoryldiglucosyldiacylglycerol and monoacylbisglycerophosphoryldiglucosyldiacylglycerol" -
Biochimica et Biophysica Acta 1214 (1994) 124-130
The structures of two phosphoglucolipids from the membrane of Acholeplasma laidlawii, strain A-EF22 were determined by high resolution 13C-, 31P- and 1H-NMR. The lipids in question are 1,2-diacyl-3-O-[glycerophosphoryl-6-O-(α-D-glucopyranosyl-(1→2)-O-α-D-glucopyranosyl)]-sn-glycerol (1) and 1,2-diacyl-3-O-[glycerophosphoryl-6-O-(α-D-glucopyranosyl-(1→2)-monoacyl-glycerophosphoryl-6-O-α-D-glucopyranosyl)]-sn-glycerol (2). Both lipids are thus derivatives of diglucosyldiacylglycerol. Previous reports on these lipids, based on insufficient chemical analyses, showed contradictory structures. A phosphoglycolipid having the structure of 2 has not been described previously.
NCBI PubMed ID: 7918591Publication DOI: 10.1016/0005-2760(94)90035-3Journal NLM ID: 0217513Publisher: Elsevier
Institutions: Department of Physical Chemistry, Umeå University, Sweden
Methods: 13C NMR, 1H NMR, TLC, 31P NMR
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5. Compound ID: 10062
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LIP-(1-1)-+
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LIP-(1-1)-Gro-(3--P--6)--+ |
| |
Gro-(3--P--6)--a-D-Glcp-(1-2)-a-D-Glcp-(1-3)-Gro
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LIP-(1-2)-+ |
Show graphically |
Structure type: oligomer
Trivial name: glycerophosphoglycolipid
Contained glycoepitopes: IEDB_142488,IEDB_144998,IEDB_144999,IEDB_146664,IEDB_161523,IEDB_232584,IEDB_241118,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 4186
Hauksson JB, Lindblom G, Rilfors L "Structures of glucolipids from the membrane of Acholeplasma laidlawii strain A-EF22. I. Glycerophosphoryldiglucosyldiacylglycerol and monoacylbisglycerophosphoryldiglucosyldiacylglycerol" -
Biochimica et Biophysica Acta 1214 (1994) 124-130
The structures of two phosphoglucolipids from the membrane of Acholeplasma laidlawii, strain A-EF22 were determined by high resolution 13C-, 31P- and 1H-NMR. The lipids in question are 1,2-diacyl-3-O-[glycerophosphoryl-6-O-(α-D-glucopyranosyl-(1→2)-O-α-D-glucopyranosyl)]-sn-glycerol (1) and 1,2-diacyl-3-O-[glycerophosphoryl-6-O-(α-D-glucopyranosyl-(1→2)-monoacyl-glycerophosphoryl-6-O-α-D-glucopyranosyl)]-sn-glycerol (2). Both lipids are thus derivatives of diglucosyldiacylglycerol. Previous reports on these lipids, based on insufficient chemical analyses, showed contradictory structures. A phosphoglycolipid having the structure of 2 has not been described previously.
NCBI PubMed ID: 7918591Publication DOI: 10.1016/0005-2760(94)90035-3Journal NLM ID: 0217513Publisher: Elsevier
Institutions: Department of Physical Chemistry, Umeå University, Sweden
Methods: 13C NMR, 1H NMR, TLC, 31P NMR
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6. Compound ID: 10113
Structure type: oligomer
Trivial name: glycosylmonoacyldiacylglycerol
Compound class: glycolipid
Contained glycoepitopes: IEDB_142488,IEDB_144998,IEDB_146664,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 4204
Hauksson JB, Lindblom G, Rilfors L "Structures of glucolipids from the membrane of Acholeplasma laidlawii strain A-EF22. II. Monoacylmonoglucosyldiacylglycerol" -
Biochimica et Biophysica Acta 1215 (1994) 341-345
The structure of one glucolipid from the membrane of Acholeplasma laidlawii, strain A-EF22, was determined. This glucolipid is synthesized only when a large fraction of saturated, straight-chain fatty acids are incorporated into the membrane lipids of strain A-EF22. The lipid was studied by 1H- and 13C-NMR spectroscopy. The structure of the lipid is 1,2-diacyl-3-O-[6-O-acyl-(α-D-glucopyranosyl)]-sn-glycerol. The result for this lipid shows that a previously published structure, based on incomplete chemical analyses, was incorrect. The phase equilibria for 1,2-diacyl-3-O-[6-O-acyl-(α-D-glucopyranosyl)]- sn-glycerol and the two dominating lipids in A. laidlawii, monoglucosyldiacylglycerol and diglucosyldiacylglycerol, are discussed and related to the chemical structure of the lipids.
NCBI PubMed ID: 7811721Publication DOI: 10.1016/0005-2760(94)90063-9Journal NLM ID: 0217513Publisher: Elsevier
Institutions: Department of Physical Chemistry, Umeå University, Sweden
Methods: 13C NMR, 1H NMR
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7. Compound ID: 10128
Structure type: oligomer
Trivial name: glycosyldiacylglycerol
Compound class: glycolipid
Contained glycoepitopes: IEDB_142488,IEDB_144998,IEDB_146664,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 4211
Karlsson OP, Dahlqvist A, Wieslander A "Activation of the membrane glucolipid synthesis in Acholeplasma laidlawii by phosphatidylglycerol and other anionic lipids" -
Journal of Biological Chemistry 269 (1994) 23484-23490
In membrane lipids of the prokaryote Acholeplasma laidlawii similar phase equilibria and a nearly constant spontaneous curvature are maintained by an extensive metabolic regulation of especially the major polar lipids monoglucosyldiacylglycerol (MGlcDAG) and diglucosyldiacylglycerol (DGlcDAG), forming nonlamellar and lamellar phases, respectively. A constant surface charge density is maintained by the anionic phospholipid fraction. These lipids are synthesized from phosphatidic acid in two competing pathways. The in vitro synthesis of MGlcDAG and DGlcDAG were totally lost upon delipidation of the membrane proteins by detergent solubilization or solvent extraction of lyophilized cells. Activities were restored by critical concentrations of anionic lipids, but not by bilayer or nonbilayer zwitterionic phospholipids or glucolipids. Phosphatidylglycerol (PG), and to a lesser extent certain other anionic lipids, could activate the synthesis of MGlcDAG in lipid bilayers, whereas the synthesis of DGlcDAG was similarly dependent upon PG only. Two endogenous phosphoglucolipids with no activating potency could partially replace the PG activator for the MGlcDAG synthesis but less so for DGlcDAG formation. A change of inert matrix from phosphatidylcholine to DGlcDAG lowered the apparent cooperativity, but enhanced the efficiency, of activation by PG for both glucolipid synthesizing enzymes, most strongly the synthesis of DGlcDAG. These results indicate that the enzymatic formation of MGlcDAG is regulated by the lipid surface charge density, whereas the consecutive step to DGlcDAG is more dependent upon the specific properties of PG. The modulating effect of the surrounding matrix on the activator efficiencies and cooperativity may constitute part of the bilayer-nonbilayer lipid regulation mechanism.
NCBI PubMed ID: 8089114Journal NLM ID: 2985121RPublisher: Baltimore, MD: American Society for Biochemistry and Molecular Biology
Institutions: Department of Biochemistry, Umeå University, Sweden
Methods: TLC, enzymatic methods
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8. Compound ID: 10129
Structure type: oligomer
Trivial name: glycosyldiacylglycerol
Compound class: glycolipid
Contained glycoepitopes: IEDB_140628,IEDB_140629,IEDB_141806,IEDB_142488,IEDB_144998,IEDB_146664,IEDB_153543,IEDB_153755,IEDB_232584,IEDB_241101,IEDB_423115,IEDB_742521,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 4211
Karlsson OP, Dahlqvist A, Wieslander A "Activation of the membrane glucolipid synthesis in Acholeplasma laidlawii by phosphatidylglycerol and other anionic lipids" -
Journal of Biological Chemistry 269 (1994) 23484-23490
In membrane lipids of the prokaryote Acholeplasma laidlawii similar phase equilibria and a nearly constant spontaneous curvature are maintained by an extensive metabolic regulation of especially the major polar lipids monoglucosyldiacylglycerol (MGlcDAG) and diglucosyldiacylglycerol (DGlcDAG), forming nonlamellar and lamellar phases, respectively. A constant surface charge density is maintained by the anionic phospholipid fraction. These lipids are synthesized from phosphatidic acid in two competing pathways. The in vitro synthesis of MGlcDAG and DGlcDAG were totally lost upon delipidation of the membrane proteins by detergent solubilization or solvent extraction of lyophilized cells. Activities were restored by critical concentrations of anionic lipids, but not by bilayer or nonbilayer zwitterionic phospholipids or glucolipids. Phosphatidylglycerol (PG), and to a lesser extent certain other anionic lipids, could activate the synthesis of MGlcDAG in lipid bilayers, whereas the synthesis of DGlcDAG was similarly dependent upon PG only. Two endogenous phosphoglucolipids with no activating potency could partially replace the PG activator for the MGlcDAG synthesis but less so for DGlcDAG formation. A change of inert matrix from phosphatidylcholine to DGlcDAG lowered the apparent cooperativity, but enhanced the efficiency, of activation by PG for both glucolipid synthesizing enzymes, most strongly the synthesis of DGlcDAG. These results indicate that the enzymatic formation of MGlcDAG is regulated by the lipid surface charge density, whereas the consecutive step to DGlcDAG is more dependent upon the specific properties of PG. The modulating effect of the surrounding matrix on the activator efficiencies and cooperativity may constitute part of the bilayer-nonbilayer lipid regulation mechanism.
NCBI PubMed ID: 8089114Journal NLM ID: 2985121RPublisher: Baltimore, MD: American Society for Biochemistry and Molecular Biology
Institutions: Department of Biochemistry, Umeå University, Sweden
Methods: TLC, enzymatic methods
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