Show legend Show as text

Structure type: oligomer
Compound class: glycolipid
Contained glycoepitopes: IEDB_141806,IEDB_142488,IEDB_146664,IEDB_161522,IEDB_241101,IEDB_983931,SB_192

• Article ID: 1747
  Button D, Hemmings NL "Lipoteichoic acid from Bacillus licheniformis 6346 MH-1. Comparative studies on the lipid portion of the lipoteichoic acid and the membrane glycolipid" - Biochemistry 15 (1976) 989-995
  
  Journal NLM ID: 0370623
  Publisher: American Chemical Society
  
   
  
  Bacillus licheniformis
  CSDB ID 106924 (all data & tools)

Show legend Show as text

Structure type: oligomer
Compound class: glycolipid
Contained glycoepitopes: IEDB_130695,IEDB_141806,IEDB_142488,IEDB_146664,IEDB_161522,IEDB_241101,IEDB_241118,IEDB_983931,SB_192

• Article ID: 1783
  Komaratat P, Kates M "The lipid composition of a halotolerant species of Staphylococcus epidermidis" - Biochimica et Biophysica Acta 398 (1975) 464-484
  
  Journal NLM ID: 0217513
  Publisher: Elsevier
  Methods: 1H NMR
  
   
  
  Staphylococcus epidermidis
  CSDB ID 108801 (all data & tools)

Show legend Show as text

Structure type: oligomer
Trivial name: glycerophosphoglycolipid
Compound class: glycolipid
Contained glycoepitopes: IEDB_141806,IEDB_142488,IEDB_146664,IEDB_161522,IEDB_241101,IEDB_241118,IEDB_983931,SB_192

• Article ID: 1785
  Fischer W, Laine RA, Nakano M "On the relationship between glycerophosphoglycolipids and lipoteichoic acids in gram-positive bacteria. II. Structures of glycerophosphoglycolipids" - Biochimica et Biophysica Acta 528 (1978) 298-308
  

  1. Eight glycerophosphoglycolipids were isolated from six Gram-positive bacteria. Besides sn-glycero-1-phospho-β-gentiobiosyldiacylglycerol (i) and sn-glycero-1-phospho-α-kojibiosyldiacylglycerol (ii), three novel structures have been established: 1,2-di-O-acyl-3-O-[6-(sn-glycero-1-phospho)-α-D-glucopyranosyl-(1→2)-(6-O-acyl-α-D-glucopyranosyl)]glycerol (iii), 1,2-di-O-acyl-3-O-[6-(sn-glycero-1-phospho)-β-D-glucopyranosyl-(1→6)-α-D-galactopyranosyl-(1→2)-α-D-glucopyranosyl]glycerol (iv), and 1,2-di-O-acyl-3-O-[6-(sn-glycero-1-phospho)-β-D-glucopyranosyl-(1→6)-α-D-galactopyranosyl-(1→2)-(6-O-acyl-α-D-glucopyranosyl)]glycerol (v). 2. Compound i was isolated from Bacillus licheniformis, Bacillus subtilis and Staphylococcus aureus, compound ii from a group B Streptococcus, compounds ii and iii from Streptococcus lactis, compounds iv and v from Lactobacillus casei. Lactobacillus plantarum contained besides compounds iv and v a glycerophosphate derivative of 1,2-di-O-acyl-3-O-[α-D-galactopyranosyl (1→2)-α-D-glucopyranosyl]glycerol. 3. Identical structural features of the described glycerophosphoglycolipids and the corresponding lipoteichoic acids are discussed.

  NCBI PubMed ID: 416848
  Journal NLM ID: 0217513
  Publisher: Elsevier
  Institutions: Institute of Physiological Chemistry, University of Erlangen-Nürnberg, Wasserturmstrasse 5, D-8520 Erlangen G.F.R.
  
   
  
  Bacillus licheniformis, Bacillus subtilis, Staphylococcus aureus
  CSDB ID 108817 (all data & tools)

Show legend Show as text

Structure type: oligomer
Trivial name: lipoteichoate derivative
Compound class: glycolipid
Contained glycoepitopes: IEDB_130695,IEDB_135813,IEDB_137340,IEDB_141806,IEDB_141807,IEDB_142488,IEDB_146664,IEDB_151531,IEDB_1597446,IEDB_161522,IEDB_241101,IEDB_241118,IEDB_983931,SB_192

• Article ID: 2581
  Fischer W, Rösel P, Koch HU "Effect of alanine ester substitution and other structural features of lipoteichoic acids on their inhibitory activity against autolysins of Staphylococcus aureus" - Journal of Bacteriology 146(2) (1981) 467-475
  

  Native substitution with the D-alanine ester of lipoteichoic acids (LTAs) affects their immunological properties, the capacity to bind divalent cations, and LTA carrier activity. In this study we tested the influence of the D-alanine ester on anti-autolytic activity, using extracellular autolysin from Staphylococcus aureus and nine LTAs with alanine/phosphorus molar ratios of between 0.23 and 0.71. The inhibitory activity, highest with alanine-free LTA, exponentially decreased with increasing alanine content, approaching zero at substitutions of greater than 0.6. Correspondingly, dipolar ionic phospholipids were not inhibitory, in contrast to negatively charged ones. Glycosylation of LTA up to an extent of 0.5 did not depress inhibitory activity, and even at a degree of 0.8 the effect was comparatively small. On comparison of LTAs from various sources, differences in lipid structures and chain lengths were without effect. The inhibitory activity drastically decreased when the glycolipid carried a single glycerophosphate residue or the hydrophilic chain had the unusual structure [6→Gal(α1→6)Gal(α1→3)Gro-(2 comes from 1 αGal)-P]n, in which digalactosyl moieties connect the α-galactosylated glycerophosphate units. Principally, the same results were obtained with the more complex system of autolysis of S. aureus cells. We hypothesize that the anti-autolytic activity of LTA resides in a sequence of glycerophosphate units and that the negative charges of appropriately spaced phosphodiester groups play a crucial role. The alanine ester effect is discussed with respect to the putative in vivo regulation of autolysins by LTA.

  NCBI PubMed ID: 6111553
  Publication DOI: 10.1128/JB.146.2.467-475.1981
  Journal NLM ID: 2985120R
  Publisher: American Society for Microbiology
  Institutions: Institut für Physiologische Chemie, Universität Erlangen-Nürnberg, D-8520 Erlangen, Federal Republic of Germany
  
   
  
  Staphylococcus aureus
  CSDB ID 131720 (all data & tools)

Show legend Show as text

Structure type: oligomer
Trivial name: lipoteichoate derivative
Compound class: glycolipid
Contained glycoepitopes: IEDB_130695,IEDB_141806,IEDB_142488,IEDB_146664,IEDB_1597446,IEDB_161522,IEDB_241101,IEDB_241118,IEDB_983931,SB_192

• Article ID: 2841
  Fischer W, Koch HU, Rösel P, Fiedler F, Schmuck P "Structural requirements of lipoteichoic acid carrier for recognitionby the poly(ribitol phosphate) polymerase from Staphylococcus aureus H. Astudy of various lipoteichoic acids, derivatives, and related compounds" - Journal of Biological Chemistry 255 (1980) 4550-4556
  

  No abstract available

  NCBI PubMed ID: 7372592
  Journal NLM ID: 2985121R
  Publisher: Baltimore, MD: American Society for Biochemistry and Molecular Biology
  Institutions: Institut fur Physiologische Chemie der Universitut Erlangen-Numberg, 0-8520 Erlangen, Federal Republic of Germany, the Lehrstuhl fur Mikrobiologie der Universitat Munchen, 0-8000 Munich, Federal Republic of Germany
  
   
  
  Staphylococcus aureus H
  CSDB ID 133461 (all data & tools)

Show legend Show as text

Structure type: oligomer
Trivial name: glycerophosphoglycolipid
Compound class: glycolipid
Contained glycoepitopes: IEDB_130695,IEDB_141806,IEDB_142488,IEDB_146664,IEDB_161522,IEDB_241101,IEDB_241118,IEDB_983931,SB_192

• Article ID: 2964
  Fischer W "Glycerophosphoglycolipids. Presumptive biosynthetic precursors of lipoteichoic acids" - Book: Chemistry and biological activities of bacterial surface amphiphiles (1981) 209-228
  
  Publication DOI: 10.1016/B978-0-12-640380-0.50024-3
  Book NLM ID: 8206058
  Publisher: Academic Press
  Editors: Gerald D. Shockman GD, Wicken AJ
  Institutions: Institut für Physiologische Chemie, Universität Erlangen - Nürnberg, Erlangen, Germany
  
   
  
  Bacillus licheniformis, Bacillus subtilis, Staphylococcus aureus
  CSDB ID 121227 (all data & tools)

Show legend Show as text

Structure type: oligomer
Compound class: glycolipid
Contained glycoepitopes: IEDB_130695,IEDB_141806,IEDB_142488,IEDB_146664,IEDB_1597446,IEDB_161522,IEDB_241101,IEDB_241118,IEDB_983931,SB_192

• Article ID: 2978
  Koch HU, Hass R, Fischer W "The role of lipoteichoic acid biosynthesis in membrane lipid metabolism of growing Staphylococcus aureus" - European Journal of Biochemistry 138 (1984) 357-363
  
  Journal NLM ID: 0107600
  Publisher: Oxford, UK: Blackwell Science Ltd. on behalf of the Federation of European Biochemical Societies
  
   
  
  Staphylococcus aureus
  CSDB ID 122771 (all data & tools)

Show legend Show as text

Structure type: oligomer
Trivial name: diglucosyldiacylglycerol
Compound class: glycolipid, diglucosyldiacylglycerol
Contained glycoepitopes: IEDB_140628,IEDB_140629,IEDB_141806,IEDB_142488,IEDB_144998,IEDB_146664,IEDB_153543,IEDB_153755,IEDB_161522,IEDB_161523,IEDB_232584,IEDB_241101,IEDB_423115,IEDB_742521,IEDB_983931,SB_192

• Article ID: 4203
  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: 7811721
  Publication DOI: 10.1016/0005-2760(94)90063-9
  Journal NLM ID: 0217513
  Publisher: Elsevier
  Institutions: Department of Physical Chemistry, Umeå University, Sweden
  Methods: 13C NMR, 1H NMR
  
   
  
  Acholeplasma laidlawii
  CSDB ID 109547 (all data & tools)
• Article ID: 10523
  Rawyler A, Meylan-Bettex M, Siegenthaler PA "(Galacto)lipid export from envelope to thylakoid membranes in intact chloroplasts. II. A general process with a key role for the envelope in the establishment of lipid asymmetry in thylakoid membranes" - Biochimica et Biophysica Acta 1233 (1995) 123-133
  

  The transfer of organelle of newly synthesized lipid molecules from inner envelope to thylakoid membranes, as well as their subsequent transbilayer distribution in these membranes, have been studied in intact chloroplasts isolated from young and mature spinach, young pea and mature lettuce leaves, using a recently developed methodology (Rawyler, A., Meylan, M. and Siegenthaler, P.A. (1992) Biochim. Biophys. Acta 1104, 331-341). Three radiolabelled precursors were used. UDP-[14C]galactose allowed to follow the fate of mono- and digalactosyldiacylglycerol (MGDG and DGDG) made from polyunsaturated, preexisting diacylglycerol (DAG), whereas [14C]acetate and [14C]glycerol 3-phosphate were used to follow the fate of MGDG and phosphatidylglycerol (PG), respectively, after de novo synthesis. MGDG, DGDG and PG molecules assembled at the envelope level were found to be exportable to thylakoids in amounts strictly proportional to the amounts synthesized, provided that the necessary substrates were not limiting. Lipid export was class-selective; under our conditions, as much as 50-80% of the MGDG, 87% of the PG and 20-30% of the DGDG synthesized were exported to thylakoids. However, within the MGDG class labelled from [14C]acetate, there was hardly any selectivity in the export of its various molecular species. For MGDG, the proportionality coefficient, which reflects the efficiency of the export process, was higher in chloroplasts from young than from mature leaves, and higher in spinach than in pea and lettuce. Temperature affected the efficiency of galactolipid export in a class-dependent way. MGDG synthesis and export had similar Q10 values of about 4 in young and 3 in mature spinach leaves, while the Q10 of DGDG export was higher than that of its synthesis. In most cases, the transmembrane distribution of labelled lipids in thylakoids was found to match closely the corresponding distribution of mass, regardless of plant age and species and of incubation time and temperature. In some cases however, small but significant differences occurred between the label and the mass transbilayer distributions of MGDG (labelled molecules more inwardly oriented), DGDG and PG (more outwardly oriented). We propose a general model in which the thylakoid lipid asymmetry is primarily preestablished in the chloroplast envelope by the topography of its lipid-synthesizing enzymes, together with the occurrence of relatively fast lateral diffusion and translocation rates of the newly synthesized lipids. Transient fusions between inner envelope and thylakoid membranes would allow lipid export by lateral diffusion and build the observed lipid asymmetry in the latter.

  chloroplast, thylakoid, lipid synthesis, mono(di)galactosyldiacylglycerol, lipid asymmetry

  NCBI PubMed ID: 7865537
  Publication DOI: 10.1016/0005-2736(94)00248-N
  Journal NLM ID: 0217513
  Publisher: Elsevier
  Institutions: Laboratoire de Physiologie Végétale, Université de Neuchâtel, Switzerland
  
   
  
  Pisum sativum, Spinacia oleracea, Lactuca sativa
  CSDB ID 109596 (all data & tools)

Show legend Show as text

Structure type: oligomer
Trivial name: type I LTA
Compound class: lipoteichoic acid
Contained glycoepitopes: IEDB_130695,IEDB_141806,IEDB_141807,IEDB_142488,IEDB_146664,IEDB_151531,IEDB_1597446,IEDB_161522,IEDB_241101,IEDB_241118,IEDB_983931,SB_192

• Article ID: 4719
  Schneewind O, Missiakas D "Lipoteichoic acids, phosphate-containing polymers in the envelope of gram-positive bacteria" - Journal of Bacteriology 196(6) (2014) 1133-1142
  

  Lipoteichoic acids (LTA) are polymers of alternating units of a polyhydroxy alkane, including glycerol and ribitol, and phosphoric acid, joined to form phosphodiester units that are found in the envelope of Gram-positive bacteria. Here we review four different types of LTA that can be distinguished on the basis of their chemical structure and describe recent advances in the biosynthesis pathway for type I LTA, d-alanylated polyglycerol-phosphate linked to di-glucosyl-diacylglycerol. The physiological functions of type I LTA are discussed in the context of inhibitors that block their synthesis and of mutants with discrete synthesis defects. Research on LTA structure and function represents a large frontier that has been investigated in only few Gram-positive bacteria.

  structure, ribitol, lipoteichoic acid, glycerol, gram-positive bacteria, envelope

  NCBI PubMed ID: 24415723
  Publication DOI: 10.1128/JB.01155-13
  Journal NLM ID: 2985120R
  Publisher: American Society for Microbiology
  Correspondence: dmissiak@bsd.uchicago.edu
  Institutions: Howard Taylor Ricketts Laboratory, Argonne National Laboratory, Lemont, Illinois, USA, Department of Microbiology, University of Chicago, Chicago, Illinois, USA
  
   
  
  Staphylococcus aureus
  CSDB ID 30446 (all data & tools)

Show legend Show as text

Structure type: oligomer
Compound class: lipoteichoic acid, lipid anchor
Contained glycoepitopes: IEDB_141806,IEDB_142488,IEDB_146664,IEDB_161522,IEDB_241101,IEDB_983931,SB_192

• Article ID: 4917
  Duda KA, Petersen S, Holst O "Structural characterization of the lipoteichoic acid isolated from Staphylococcus sciuri W620" - Carbohydrate Research 430 (2016) 44-47
  

  Lipoteichoic acid (LTA) is an important cell envelope compound of Gram-positive bacteria. LTA isolated from allergy-protective Staphylococcus sciuri W620 strain was characterized by chemical analyses as well as 1D and 2D NMR experiments. Compositional analyses indicated the presence of glycerol (Gro), phosphate-Gro, alanine-Gro, glucose (Glc) and fatty acids. The studied strain produced LTA with backbone composed of glycerol-phosphate repeating units only substituted with d-alanine (Ala) and the lipid anchor, typically for genus Staphyloccocus, possessing the structure β-d-Glcp(1→6)-β-d-Glcp(1→3)-1,2-diacyl-sn-Gro.

  structure, NMR analysis, lipoteichoic acid, LTA structure, Allergy-protection, Staphylococcus sciuri

  NCBI PubMed ID: 27196311
  Publication DOI: 10.1016/j.carres.2016.04.026
  Journal NLM ID: 0043535
  Publisher: Elsevier
  Correspondence: kduda@fz-borstel.de
  Institutions: Junior Research Group Allergobiochemistry, Division of Structural Biochemistry, Priority Area Asthma and Allergies, Research Center Borstel, Leibniz-Center for Medicine and Biosciences, Airway Research Center North (ARCN), Member of the German Center for Lung Research (DZL), Parkallee 4a/c, D-23845 Borstel, Germany
  Methods: 13C NMR, 1H NMR, NMR-2D, GLC-MS, de-O-acylation, 31P NMR, acid hydrolysis, GLC, composition analysis, NMR-1D, methanolysis, HPLC
  
   
  
  Staphylococcus sciuri W620
  CSDB ID 11689 (all data & tools)

Show legend Show as text

Structure type: oligomer ; 864-920
Compound class: glycoglycerolipid
Contained glycoepitopes: IEDB_141806,IEDB_142488,IEDB_146664,IEDB_161522,IEDB_241101,IEDB_983931,SB_192

• Article ID: 5598
  Wicke C, Hüners M, Wray V, Nimtz M, Bilitewski U, Lang S "Production and structure elucidation of glycoglycerolipids from a marine sponge-associated microbacterium species" - Journal of Natural Products 63(5) (2000) 621-626
  

  The bacterium Microbacterium sp., isolated from the sponge Halichondria panicea, produced four unusual cell-associated glycoglycerolipids and one diphosphatidylglycerol when grown on marine broth and on artificial seawater media. The lipids were isolated by chromatography on silica columns and their structures elucidated using a combination of multidimensional NMR and MS techniques. The main compound was 1-O-acyl-3-[α-glucopyranosyl-(1-3)-(6-O-acyl-α-mannopyranosyl)]glycerol (GGL.2) with 14-methyl-hexadecanoic acid and 12-methyl-tetradecanoic acid positioned at C-6 of the mannose unit and at the glycerol moiety. Glycolipid production was correlated with growth and reached a maximum value of 200 mg/L when grown on artificial seawater medium with 20 g/L glucose. The main compound decreased the surface tension of water down to 33 mN/m and the interfacial tension of the water/n-hexadecane system down to 5 mN/m. In addition to this good surface-active behavior, the main glycoglycerolipid showed antitumor activities

  glycolipids, biosurfactant, antitumor activity, Microbacterium sp.

  NCBI PubMed ID: 10843572
  Publication DOI: 10.1021/np990313b
  Journal NLM ID: 7906882
  Publisher: American Society of Pharmacognosy
  Correspondence: s.lang@tu-bs.de
  Institutions: Institut für Biochemie und Biotechnologie, Technische Universität Braunschweig, Abt. Biotechnologie, Braunschweig, Germany, Gesellschaft für Biotechnologische Forschung mbH, Braunschweig, Germany
  Methods: 13C NMR, 1H NMR, NMR-2D, GC-EI-MS, TLC, ESI-MS, MS/MS, methanolysis, extraction, cell growth, derivatization, LC, antimicrobial assay, centrifugation, determination of surface tension
  
   
  
  Microbacterium sp. DSM 12583
  CSDB ID 47723 (all data & tools)

Show legend Show as text

Structure type: oligomer
Compound class: lipoteichoic acid
Contained glycoepitopes: IEDB_141806,IEDB_141807,IEDB_142488,IEDB_146664,IEDB_151531,IEDB_161522,IEDB_241101,IEDB_241118,IEDB_983931,SB_192

• Article ID: 5781
  Hesser AR, Schaefer K, Lee W, Walker S "Lipoteichoic acid polymer length is determined by competition between free starter units" - Proceedings of the National Academy of Sciences of the USA 117(47) (2020) 29669-29676
  

  Carbohydrate polymers exhibit incredible chemical and structural diversity, yet are produced by polymerases without a template to guide length and composition. As the length of carbohydrate polymers is critical for their biological functions, understanding the mechanisms that determine polymer length is an important area of investigation. Most Gram-positive bacteria produce anionic glycopolymers called lipoteichoic acids (LTA) that are synthesized by lipoteichoic acid synthase (LtaS) on a diglucosyl-diacylglycerol (Glc2DAG) starter unit embedded in the extracellular leaflet of the cell membrane. LtaS can use phosphatidylglycerol (PG) as an alternative starter unit, but PG-anchored LTA polymers are significantly longer, and cells that make these abnormally long polymers exhibit major defects in cell growth and division. To determine how LTA polymer length is controlled, we reconstituted Staphylococcus aureus LtaS in vitro. We show that polymer length is an intrinsic property of LtaS that is directly regulated by the identity and concentration of lipid starter units. Polymerization is processive, and the overall reaction rate is substantially faster for the preferred Glc2DAG starter unit, yet the use of Glc2DAG leads to shorter polymers. We propose a simple mechanism to explain this surprising result: free starter units terminate polymerization by displacing the lipid anchor of the growing polymer from its binding site on the enzyme. Because LtaS is conserved across most Gram-positive bacteria and is important for survival, this reconstituted system should be useful for characterizing inhibitors of this key cell envelope enzyme.

  chemistry, microbiology, chemical, biology, lipoteichoic acid, medical, processivity, polymerase, pharmacy

  NCBI PubMed ID: 33172991
  Publication DOI: 10.1073/pnas.2008929117
  Journal NLM ID: 7505876
  Publisher: National Academy of Sciences
  Correspondence: suzanne_walker@hms.harvard.edu
  Institutions: Department of Microbiology, Harvard Medical School, Boston, MA 02115, Department of Chemistry and Chemical Biology, Harvard University, Cambridge, MA 02138, School of Pharmacy, Sungkyunkwan University, Suwon 16419, Republic of Korea
  Methods: PCR, TLC, MS, serological methods, genetic methods, biochemical methods, PAGE, SEC
  
   
  
  Staphylococcus aureus
  CSDB ID 32116 (all data & tools)