Show legend Show as text

Structure type: oligomer
Trivial name: a-kojibiosyldiacylglycerol
Compound class: glycolipid
Contained glycoepitopes: IEDB_142488,IEDB_144998,IEDB_146664,IEDB_161523,IEDB_232584,IEDB_983931,SB_192

• Article ID: 1684
  Fischer W "Molecular analysis of lipid macroamphiphiles by hydrophobic interlaction chromatography, exemplified with lipoteichoic acids" - Analytical Biochemistry 208 (1993) 49-56
  
  Journal NLM ID: 0370535
  Publisher: Academic Press
  
   
  
  Enterococcus hirae
  CSDB ID 102627 (all data & tools)
• Article ID: 1726
  Brundish DE, Shaw N, Baddiley J "Bacterial glycolipids. Glycosyl diglycerides in gram-positive bacteria" - Biochemical Journal 99 (1966) 546-549
  
  Journal NLM ID: 2984726R
  Publisher: London, UK : Published by Portland Press on behalf of the Biochemical Society
  
   
  
  Streptococcus lactis N
  CSDB ID 105899 (all data & tools)
• Article ID: 2510
  Fischer W, Seyferth W "1-[O-a-glucopyranosyl-(1->2)-O-a-glucopyranosyl]-glycerin from the glyclipids of Streptococcus faecalis and Streptococcus lactis" - Hoppe-Seyler's Zeitschrift fur Physiologische Chemie [German] 349 (1968) 1662-1672
  
  Journal NLM ID: 2985060R
  Publisher: Berlin: Walter De Gruyter
  
   
  
  Streptococcus faecalis, Streptococcus lactis
  CSDB ID 129726 (all data & tools)
• Article ID: 2615
  Ishizuka I, Yamakawa T "Glycosyl glycerides from Streptococcus hemolyticus strain D-58" - Journal of Biochemistry 64 (1968) 13-23
  
  Journal NLM ID: 0376600
  Publisher: Japanese Biochemical Society
  Methods: 1H NMR, IR
  
   
  
  Streptococcus pyogenes D-58
  CSDB ID 131858 (all data & tools)
• Article ID: 2625
  Pieringer RA "The metabolism of glyceride glycolipids. I. Biosynthesis of monoglucosyl diglyceride and diglucosyl diglyceride by glucosyltransferase pathways in Streptococcus faecalis" - Journal of Biological Chemistry 243 (1968) 4894-4903
  
  Journal NLM ID: 2985121R
  Publisher: Baltimore, MD: American Society for Biochemistry and Molecular Biology
  
   
  
  Streptococcus faecium
  CSDB ID 133152 (all data & tools)

Show legend Show as text

Structure type: oligomer
Compound class: glycolipid
Contained glycoepitopes: IEDB_130695,IEDB_142488,IEDB_144998,IEDB_144999,IEDB_146664,IEDB_161523,IEDB_167835,IEDB_232584,IEDB_241118,IEDB_983931,SB_192

• Article ID: 1785
  Fischer W, Nakano M, Laine RA, Bohrer W "On the relationship between glycerophosphoglycolipids and lipoteichoic acids in gram-positive bacteria. I. The occurrence of phosphoglycolipids" - Biochimica et Biophysica Acta 528 (1978) 288-297
  

  1. Gram-positive bacteria out of the families of Streptococcaceae, Lactobacillaceae, Micrococcaceae and Bacillaceae were investigated with respect to the occurrence and the concentration of phosphoglycolipids. 2. Phosphatidylglycolipids occur exclusively in group D Streptococci and in Streptococcus hemolyticus D-58. Phosphatidyl-α-kojibiosyldiacylglycerol, the prevalent species, accounts for up to 28% of the polar lipids. The related glycerophospho-phosphatidyl-α-kojibiosyldiacylglycerol is restricted to Streptococcus faecalis. 3. Glycerophosphoglycolipids, usually minor components, comprise thirteen compounds most of which have so far not been described. Except Micrococcus lysodeikticus all examined bacteria contained one or more glycerophosphoglycolipids. Their occurrence parallels, therefore, that of lipoteichoic acids, which supports the hypothesis of a metabolic relationship between these two membrane components.

  NCBI PubMed ID: 638158
  Publication DOI: 10.1016/0005-2760(78)90018-8
  Journal NLM ID: 0217513
  Publisher: Elsevier
  Institutions: Institute of Physiological Chemistry, University of Erlangen-Nürnberg, Wasserturmstrasse 5, D-8520 Erlangen G.F.R., nstitute of Physiological Chemistry, University of Erlangen-Nürnberg, Wasserturmstrasse 5, D-8520 ErlangenG.F.R.
  
   
  
  Streptococcus hemolyticus D-58
  CSDB ID 108812 (all data & tools)

Show legend Show as text

Structure type: oligomer
Trivial name: phosphatidyl-kojibiosyl diacylglycerol
Compound class: glycolipid
Contained glycoepitopes: IEDB_130695,IEDB_142488,IEDB_144998,IEDB_144999,IEDB_146664,IEDB_161523,IEDB_167835,IEDB_232584,IEDB_241118,IEDB_983931,SB_192

• Article ID: 1785
  Fischer W, Nakano M, Laine RA, Bohrer W "On the relationship between glycerophosphoglycolipids and lipoteichoic acids in gram-positive bacteria. I. The occurrence of phosphoglycolipids" - Biochimica et Biophysica Acta 528 (1978) 288-297
  

  1. Gram-positive bacteria out of the families of Streptococcaceae, Lactobacillaceae, Micrococcaceae and Bacillaceae were investigated with respect to the occurrence and the concentration of phosphoglycolipids. 2. Phosphatidylglycolipids occur exclusively in group D Streptococci and in Streptococcus hemolyticus D-58. Phosphatidyl-α-kojibiosyldiacylglycerol, the prevalent species, accounts for up to 28% of the polar lipids. The related glycerophospho-phosphatidyl-α-kojibiosyldiacylglycerol is restricted to Streptococcus faecalis. 3. Glycerophosphoglycolipids, usually minor components, comprise thirteen compounds most of which have so far not been described. Except Micrococcus lysodeikticus all examined bacteria contained one or more glycerophosphoglycolipids. Their occurrence parallels, therefore, that of lipoteichoic acids, which supports the hypothesis of a metabolic relationship between these two membrane components.

  NCBI PubMed ID: 638158
  Publication DOI: 10.1016/0005-2760(78)90018-8
  Journal NLM ID: 0217513
  Publisher: Elsevier
  Institutions: Institute of Physiological Chemistry, University of Erlangen-Nürnberg, Wasserturmstrasse 5, D-8520 Erlangen G.F.R., nstitute of Physiological Chemistry, University of Erlangen-Nürnberg, Wasserturmstrasse 5, D-8520 ErlangenG.F.R.
  
   
  
  Streptococcus hemolyticus D-58
  CSDB ID 108813 (all data & tools)

Show legend Show as text

Structure type: oligomer
Trivial name: phosphatidyl-a-kojitriosyl diacylglycerol
Compound class: glycolipid
Contained glycoepitopes: IEDB_130695,IEDB_142488,IEDB_144998,IEDB_144999,IEDB_146664,IEDB_161523,IEDB_167835,IEDB_232584,IEDB_241118,IEDB_983931,SB_192

• Article ID: 1785
  Fischer W, Nakano M, Laine RA, Bohrer W "On the relationship between glycerophosphoglycolipids and lipoteichoic acids in gram-positive bacteria. I. The occurrence of phosphoglycolipids" - Biochimica et Biophysica Acta 528 (1978) 288-297
  

  1. Gram-positive bacteria out of the families of Streptococcaceae, Lactobacillaceae, Micrococcaceae and Bacillaceae were investigated with respect to the occurrence and the concentration of phosphoglycolipids. 2. Phosphatidylglycolipids occur exclusively in group D Streptococci and in Streptococcus hemolyticus D-58. Phosphatidyl-α-kojibiosyldiacylglycerol, the prevalent species, accounts for up to 28% of the polar lipids. The related glycerophospho-phosphatidyl-α-kojibiosyldiacylglycerol is restricted to Streptococcus faecalis. 3. Glycerophosphoglycolipids, usually minor components, comprise thirteen compounds most of which have so far not been described. Except Micrococcus lysodeikticus all examined bacteria contained one or more glycerophosphoglycolipids. Their occurrence parallels, therefore, that of lipoteichoic acids, which supports the hypothesis of a metabolic relationship between these two membrane components.

  NCBI PubMed ID: 638158
  Publication DOI: 10.1016/0005-2760(78)90018-8
  Journal NLM ID: 0217513
  Publisher: Elsevier
  Institutions: Institute of Physiological Chemistry, University of Erlangen-Nürnberg, Wasserturmstrasse 5, D-8520 Erlangen G.F.R., nstitute of Physiological Chemistry, University of Erlangen-Nürnberg, Wasserturmstrasse 5, D-8520 ErlangenG.F.R.
  
   
  
  Streptococcus hemolyticus D-58
  CSDB ID 108814 (all data & tools)

Show legend Show as text

Structure type: oligomer
Compound class: glycolipid
Contained glycoepitopes: IEDB_130695,IEDB_142488,IEDB_144998,IEDB_144999,IEDB_146664,IEDB_161523,IEDB_232584,IEDB_241118,IEDB_983931,SB_192

• Article ID: 1785
  Fischer W, Nakano M, Laine RA, Bohrer W "On the relationship between glycerophosphoglycolipids and lipoteichoic acids in gram-positive bacteria. I. The occurrence of phosphoglycolipids" - Biochimica et Biophysica Acta 528 (1978) 288-297
  

  1. Gram-positive bacteria out of the families of Streptococcaceae, Lactobacillaceae, Micrococcaceae and Bacillaceae were investigated with respect to the occurrence and the concentration of phosphoglycolipids. 2. Phosphatidylglycolipids occur exclusively in group D Streptococci and in Streptococcus hemolyticus D-58. Phosphatidyl-α-kojibiosyldiacylglycerol, the prevalent species, accounts for up to 28% of the polar lipids. The related glycerophospho-phosphatidyl-α-kojibiosyldiacylglycerol is restricted to Streptococcus faecalis. 3. Glycerophosphoglycolipids, usually minor components, comprise thirteen compounds most of which have so far not been described. Except Micrococcus lysodeikticus all examined bacteria contained one or more glycerophosphoglycolipids. Their occurrence parallels, therefore, that of lipoteichoic acids, which supports the hypothesis of a metabolic relationship between these two membrane components.

  NCBI PubMed ID: 638158
  Publication DOI: 10.1016/0005-2760(78)90018-8
  Journal NLM ID: 0217513
  Publisher: Elsevier
  Institutions: Institute of Physiological Chemistry, University of Erlangen-Nürnberg, Wasserturmstrasse 5, D-8520 Erlangen G.F.R., nstitute of Physiological Chemistry, University of Erlangen-Nürnberg, Wasserturmstrasse 5, D-8520 ErlangenG.F.R.
  
   
  
  Streptococcus
  CSDB ID 108815 (all data & tools)

Show legend Show as text

Structure type: oligomer
Compound class: glycolipid
Contained glycoepitopes: IEDB_142488,IEDB_144998,IEDB_146664,IEDB_161523,IEDB_232584,IEDB_983931,SB_192

• Article ID: 2330
  Fischer W, Laine RA, Nakano M, Schuster D, Egge H "The structure of acyl-a-kojibiosyldiacylglycerol from Streptococcus lactis" - Chemistry and Physics of Lipids 21 (1978) 103-112
  
  Journal NLM ID: 0067206
  Methods: EI-MS
  
   
  
  Streptococcus lactis N
  CSDB ID 121115 (all data & tools)

Show legend Show as text

Structure type: oligomer
Compound class: glycolipid
Contained glycoepitopes: IEDB_130695,IEDB_142488,IEDB_144998,IEDB_144999,IEDB_146664,IEDB_161523,IEDB_232584,IEDB_241118,IEDB_983931,SB_192

• Article ID: 2582
  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
  
   
  
  Streptococcus hemolyticus
  CSDB ID 131727 (all data & tools)

Show legend Show as text

Structure type: oligomer
Trivial name: a-kojibiosyldiacylglycerol, triglucosyldiacylglycerol
Compound class: glycolipid
Contained glycoepitopes: IEDB_142488,IEDB_144998,IEDB_146664,IEDB_161523,IEDB_232584,IEDB_983931,SB_192

• Article ID: 2615
  Ishizuka I, Yamakawa T "Glycosyl glycerides from Streptococcus hemolyticus strain D-58" - Journal of Biochemistry 64 (1968) 13-23
  
  Journal NLM ID: 0376600
  Publisher: Japanese Biochemical Society
  Methods: 1H NMR, IR
  
   
  
  Streptococcus pyogenes D-58
  CSDB ID 131859 (all data & tools)

Show legend Show as text

Structure type: oligomer
Compound class: glycolipid
Contained glycoepitopes: IEDB_130695,IEDB_142488,IEDB_144998,IEDB_144999,IEDB_146664,IEDB_1597446,IEDB_161523,IEDB_167835,IEDB_232584,IEDB_241118,IEDB_983931,SB_192

• Article ID: 2836
  Toon P, Brown PE, Baddiley J "The lipid-teichoic acid complex in the cytoplasmic membrane of Streptococcus faecalis N.C.I.B. 8191" - Biochemical Journal 127 (1972) 399-409
  

  1. A lipid-teichoic acid complex was isolated from Streptococcus faecalis N.C.I.B. 8191. The covalent nature of the linkage between teichoic acid and lipid was established. 2. The complex exhibits macromolecular properties in solution, and ultracentrifugation studies show that these are due to micelle formation. 3. From chemical studies it is concluded that the teichoic acid is a poly(glycerol phosphate) in which some of the glycerol hydroxyl groups possess kojibiosyl [2-O-α-d-glucopyranosyl-(1→2)-α-d-glucopyranosyl] substituents, together with d-alanine ester residues. 4. The lipid is 1-kojibiosyl diglyceride, already known as a membrane component of this organism, with probably a phosphatidyl substituent. The phosphatidyl kojibiosyl diglyceride is attached to the teichoic acid through a phosphodiester linkage, and the chain of the teichoic acid contains 28-35 units. 5. Although the complex represents the whole of the membrane teichoic acid in this organism, only about 12% of the membrane glycolipid is associated with teichoic acid. 6. Two phosphatidyl glycolipids, closely resembling that bearing the teichoic acid, were isolated from the lipids of the organism and were partly characterized.

  NCBI PubMed ID: 4627730
  Publication DOI: 10.1042/bj1270399
  Journal NLM ID: 2984726R
  Publisher: London, UK : Published by Portland Press on behalf of the Biochemical Society
  Institutions: Microbiological Chemistry Research Laboratory, School of Chemistry, University of Newcastle upon Tyne, Newcastle upon Tyne NE1 7RU, U.K.
  
   
  
  Enterococcus faecalis NCIB 8191
  CSDB ID 105912 (all data & tools)

Show legend Show as text

Structure type: oligomer
Trivial name: glycerophospho-phosphatidyl-a-kojibiosyldiacylglycerol
Compound class: glycolipid
Contained glycoepitopes: IEDB_130695,IEDB_135396,IEDB_142488,IEDB_144998,IEDB_144999,IEDB_146664,IEDB_161523,IEDB_232584,IEDB_241118,IEDB_983931,SB_192

• Article ID: 1785
  Fischer W, Nakano M, Laine RA, Bohrer W "On the relationship between glycerophosphoglycolipids and lipoteichoic acids in gram-positive bacteria. I. The occurrence of phosphoglycolipids" - Biochimica et Biophysica Acta 528 (1978) 288-297
  

  1. Gram-positive bacteria out of the families of Streptococcaceae, Lactobacillaceae, Micrococcaceae and Bacillaceae were investigated with respect to the occurrence and the concentration of phosphoglycolipids. 2. Phosphatidylglycolipids occur exclusively in group D Streptococci and in Streptococcus hemolyticus D-58. Phosphatidyl-α-kojibiosyldiacylglycerol, the prevalent species, accounts for up to 28% of the polar lipids. The related glycerophospho-phosphatidyl-α-kojibiosyldiacylglycerol is restricted to Streptococcus faecalis. 3. Glycerophosphoglycolipids, usually minor components, comprise thirteen compounds most of which have so far not been described. Except Micrococcus lysodeikticus all examined bacteria contained one or more glycerophosphoglycolipids. Their occurrence parallels, therefore, that of lipoteichoic acids, which supports the hypothesis of a metabolic relationship between these two membrane components.

  NCBI PubMed ID: 638158
  Publication DOI: 10.1016/0005-2760(78)90018-8
  Journal NLM ID: 0217513
  Publisher: Elsevier
  Institutions: Institute of Physiological Chemistry, University of Erlangen-Nürnberg, Wasserturmstrasse 5, D-8520 Erlangen G.F.R., nstitute of Physiological Chemistry, University of Erlangen-Nürnberg, Wasserturmstrasse 5, D-8520 ErlangenG.F.R.
  
   
  
  Streptococcus faecalis
  CSDB ID 108816 (all data & tools)

Show legend Show as text

Structure type: oligomer
Trivial name: lipoteichoate derivative
Compound class: glycolipid
Contained glycoepitopes: IEDB_130695,IEDB_142488,IEDB_144998,IEDB_144999,IEDB_146664,IEDB_161523,IEDB_232584,IEDB_241118,IEDB_983931,SB_192

• Article ID: 1786
  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.
  
   
  
  Streptococcus lactis
  CSDB ID 108819 (all data & tools)

Show legend Show as text

Structure type: oligomer
Trivial name: lipoteichoate derivative
Compound class: glycolipid
Contained glycoepitopes: IEDB_130695,IEDB_142488,IEDB_144998,IEDB_144999,IEDB_146664,IEDB_161523,IEDB_232584,IEDB_241118,IEDB_983931,SB_192

• Article ID: 1786
  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.
  
   
  
  Streptococcus lactis
  CSDB ID 208819 (all data & tools)

Show legend Show as text

Structure type: oligomer
Compound class: glycolipid, lipoteichoic acid, glycerophosphoglycolipid
Contained glycoepitopes: IEDB_130695,IEDB_142488,IEDB_144998,IEDB_144999,IEDB_146664,IEDB_161523,IEDB_167835,IEDB_232584,IEDB_241118,IEDB_983931,SB_192

• Article ID: 2840
  Kessler RE, Shockman GD "Precursor-product relationship of intracellular and extracellularlipoteichoic acids of Streptococcus faecalis" - Journal of Bacteriology 137 (1979) 869-877
  
  Journal NLM ID: 2985120R
  Publisher: American Society for Microbiology
  
   
  
  Enterococcus faecalis
  CSDB ID 131713 (all data & tools)

Show legend Show as text

Structure type: oligomer
Trivial name: lipoteichoate derivative
Compound class: glycolipid
Contained glycoepitopes: IEDB_130695,IEDB_136906,IEDB_137472,IEDB_141794,IEDB_142488,IEDB_144998,IEDB_144999,IEDB_146664,IEDB_151528,IEDB_1597446,IEDB_161523,IEDB_190606,IEDB_232584,IEDB_241118,IEDB_983931,SB_192,SB_7

• Article ID: 2582
  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
  
   
  
  Streptococcus lactis NCDO 712
  CSDB ID 131723 (all data & tools)

Show legend Show as text

Structure type: oligomer
Trivial name: lipoteichoate derivative
Compound class: glycolipid
Contained glycoepitopes: IEDB_130695,IEDB_135614,IEDB_140628,IEDB_140629,IEDB_141806,IEDB_142488,IEDB_144998,IEDB_144999,IEDB_146664,IEDB_153543,IEDB_153755,IEDB_158538,IEDB_158555,IEDB_1597446,IEDB_161523,IEDB_167835,IEDB_232584,IEDB_232585,IEDB_2346541,IEDB_241101,IEDB_241118,IEDB_420421,IEDB_423115,IEDB_742521,IEDB_857742,IEDB_983931,SB_192

• Article ID: 2582
  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
  
   
  
  Streptococcus faecalis ATCC 9790
  CSDB ID 131724 (all data & tools)