Show legend Show as text

Structure type: oligomer
Aglycon: lipid A
Compound class: core oligosaccharide
Contained glycoepitopes: IEDB_130650,IEDB_135813,IEDB_136044,IEDB_137340,IEDB_137472,IEDB_140628,IEDB_140629,IEDB_141794,IEDB_141806,IEDB_141807,IEDB_142487,IEDB_142488,IEDB_144998,IEDB_146664,IEDB_151531,IEDB_190606,IEDB_232584,IEDB_232585,IEDB_742521,IEDB_983931,SB_165,SB_166,SB_187,SB_192,SB_195,SB_6,SB_7,SB_88

• Article ID: 380
  Skurnik M, Zhang L "Molecular genetics and biochemistry of Yersinia lipopolysaccharide" - APMIS: Acta Pathologica, Microbiologica, et Immunologica Scandinavica 104(12) (1996) 849-872
  

  Studies on the molecular genetics of bacterial LPS serve at least two main purposes: (i) to help develop an understanding of the biology, biochemistry and genetics of this bacterial surface macromolecule, and (ii) to provide a basis for both vaccine development and virulence experiments. Both of these goals have been the driving force in studies of Yersinia LPS carried out during the last decade. Here we will review the progress made in the molecular genetics and biochemistry of Yersinia LPS. A deep understanding has been achieved with respect to Y. enterocolitica serotype O:3, reaching as far as a detailed analysis of the gene clusters directing the biosynthesis of the outer core oligosaccharide and of the O-ag. The O-ag gene clusters of Y. enterocolitica serotype O:8 and Y. pseudotuberculosis serotypes O:2a and O:5a have also been cloned and partially characterized LPS biosynthesis of these Yersinia species includes examples of the two major variations recognized in the biosynthesis of this macromolecule: (i) homopolymeric or O-antigen polymerase-independent biosynthesis, and (ii) heteropolymeric or O-antigen polymerase-dependent biosynthesis.

  Lipopolysaccharide, genetic, gene, genetics, O-antigen, biochemistry, Yersinia, molecular genetics

  NCBI PubMed ID: 9048864
  Publication DOI: 10.1111/j.1699-0463.1996.tb04951.x
  Journal NLM ID: 8803400
  Publisher: Copenhagen: Munksgaard
  Institutions: Turku Centre for Biotechnology, University of Turku, Finland, department of Medical Microbiology, University of Turku, Turku, Finland
  
   
  
  Yersinia pseudotuberculosis
  CSDB ID 31515 (all data & tools)

Show legend Show as text

Structure type: oligomer
Compound class: glycolipid, trehalolipid
Contained glycoepitopes: IEDB_142488,IEDB_144998,IEDB_146664,IEDB_742521,IEDB_983931,SB_192

• Article ID: 501
  Pasciak M, Holst O, Lindner B, Mierzchala M, Grzegorzewicz A, Mordarska H, Gamian A "Structural and serological characterization of the major glycolipid from Rothia mucilaginosa" - Biochimica et Biophysica Acta: General Subjects 1675(1-3) (2004) 54-61
  

  Structural studies on the major glycolipid isolated from Rothia mucilaginosa were carried out utilising specific chemical degradation, NMR spectroscopy and matrix-assisted laser-desorption/ionization time of flight mass spectrometry (MALDI TOF-MS). The glycolipid was found to be a dimannosylacylmonoglyceride in which the carbohydrate part was the glycerol-linked dimannoside α-D-Manp-(1→3)-α-D-Manp-(1→3)-sn-Gro (Man A-Man B-Gro), of which Man B was esterified at O-6 by a fatty acid residue. A second fatty acid substituted the secondary methylene position of the glycerol residue, in contrast to the glycolipid previously found in R. dentocariosa and Saccharopolyspora strains, in which the second fatty acid esterified the primary methylene position of glycerol. Results of the ELISA experiment with rabbit specific antibacterial sera indicate that these two major glycolipids are antigenic, and the patterns of serological reactivity are similar but not identical.

  NMR, structure, glycolipid, Rothia mucilaginosa, Stomatococcus, Opportunistic agent, Dimannosylacylmonoglyceride

  NCBI PubMed ID: 15535967
  Publication DOI: 10.1016/j.bbagen.2004.08.004
  Journal NLM ID: 0217513
  Publisher: Elsevier
  Correspondence: gamian@immuno.iitd.pan.wroc.pl
  Institutions: Institute of Immunology and Experimental Therapy, Polish Academy of Sciences, Wroclaw, Poland, Division of Structural Biochemistry, Research Center Borstel, Leibniz Center for Medicine and Biosciences, Germany, Division of Biophysics, Research Center Borstel, Leibniz Center for Medicine and Biosciences, Borstel, Germany
  Methods: NMR-2D, NMR, MALDI-TOF MS
  
   
  
  Nocardiopsis dassonvillei N2
  CSDB ID 9343 (all data & tools)
• Article ID: 5328
  Philp JC, Kuyukina MS, Ivshina IB, Dunbar SA, Christofi N, Lang S, Wray V "Alkanotrophic Rhodococcus ruber as a biosurfactant producer" - Applied Microbiology and Biotechnology 59(2-3) (2002) 318-324
  

  In this report we examined the structure and properties of surface-active lipids of Rhodococcus ruber. Most historical interest has been in the glycolipids of Rhodococcus erythropolis, which have been extensively characterised. R. erythropolis has been of interest due to its great metabolic diversity. Only recently has the metabolic potential of R. ruber begun to be explored. One major difference in the two species is that most R. ruber strains are able to oxidise the gaseous alkanes propane and butane. In preparation for investigation of the effects of gas metabolism on biosurfactant production, we set out to characterise the biosurfactants produced during growth on liquid n-alkanes and to compare these with R. erythropolis glycolipids.

  lipid, biosurfactant, propane, alkane, butane, Rhodococcus ruber

  NCBI PubMed ID: 12111164
  Publication DOI: 10.1007/s00253-002-1018-4
  Journal NLM ID: 8406612
  Publisher: Springer
  Correspondence: j.philp@napier.ac.uk
  Institutions: School of Life Sciences, Napier University, Edinburgh, Scotland, Institute of Ecology and Genetics of Microorganisms (IEGM), Perm, Russia, Technical University of Braunschweig, Institute of Biochemistry and Biotechnology, Braunschweig, Germany, German Research Centre for Biotechnology, Department of Structure Research, Braunschweig, Germany
  Methods: 13C NMR, 1H NMR, NMR-2D, ESI-MS, GC, extraction, HPTLC, hydrazinolysis, column chromatography, cell growth, determination of surface tension
  
   
  
  Rhodococcus ruber IEGM 231
  CSDB ID 45655 (all data & tools)
• Article ID: 5655
  Varvaresou A, Iakovou K "Biosurfactants in cosmetics and biopharmaceuticals" - Letters in Applied Microbiology 61(3) (2015) 214-223
  

  Biosurfactants are surface-active biomolecules that are produced by various micro-organisms. They show unique properties i.e. lower toxicity, higher biodegradability and environmental compatibility compared to their chemical counterparts. Glycolipids and lipopeptides have prompted application in biotechnology and cosmetics due to their multi-functional profile i.e. detergency, emulsifying, foaming and skin hydrating properties. Additionally, some of them can be served as antimicrobials. In this study the current status of research and development on rhamnolipids, sophorolipids, mannosylerythritol lipids, trehalipids, xylolipids and lipopeptides particularly their commercial application in cosmetics and biopharmaceuticals, is described

  biotechnology, biopharmaceuticals, biosurfactants, antimicrobials, cosmetics

  NCBI PubMed ID: 25970073
  Publication DOI: 10.1111/lam.12440
  Journal NLM ID: 8510094
  Correspondence: varvaresou@pharm.uoa.gr
  Institutions: Laboratory of Cosmetology, Department of Aesthetics and Cosmetology, Technological Educational Institution of Athens, Athens, Greece, Department of Drugs, Ministry of Health, Athens, Greece
  
   
  
  Micrococcus luteus, Rhodococcus erythropolis
  CSDB ID 48230 (all data & tools)
• Article ID: 5664
  Lang S, Philp JC "Surface-active lipids in rhodococci" - Antonie van Leeuwenhoek 74(1-3) (1998) 59-70
  

  Like other hydrocarbon-oxidising bacteria, rhodococci respond to the presence of alkanes by producing biosurfactant molecules to improve their ability to utilise these hydrophobic compounds as growth substrates. In the rhodococci these surfactants are predominantly glycolipids, the majority of which remain cell-bound during unrestricted growth. Most work has been done on the trehalose mycolates formed by Rhodococcus erythropolis, but nitrogen-limited conditions lead to the production of anionic trehalose tetraesters also. As surfactants, these compounds, whether purified or in crude form, are able to reduce the surface tension of water from 72 mN m-1 to a low of 26, thus making them among the most potent biosurfactants known. They are also able to reduce the interfacial tension between water and a hydrophobic phase (e.g. n-hexadecane) from 43 mN m-1 to values less than one (Table 1). Biosurfactants have about a ten- to 40-fold lower critical micelle concentration than synthetic surfactants. Such properties suggest a range of industrial applications, where a variety of surface-active characteristics are appropriate. Interest in biosurfactants as industrial chemicals results from the toxicity of many petrochemical-derived surfactants. Currently world-wide surfactant production is on a very large scale, and the demand for them is increasing. However, the drive towards less environmentally damaging chemicals makes biosurfactants attractive as they have lower toxicity. The reason they have not achieved a significant market share is the cost of production, which is considerably higher than for synthetic surfactants. This problem is being addressed using several strategies. An approach where there is great scope for improvement with the rhodococci is an understanding of the genetic basis of glycolipid production, which is largely unknown. They may find applications in the near future in the environmental remediation industries, where the requirement for purified molecules is of less importance. This review summarises knowledge of the chemistry, biochemistry and production of Rhodococcus surface-active lipids. Where they have been used, or there is potential for use, in industrial applications is discussed

  glycolipids, biosurfactants, remediation, rhodococci

  NCBI PubMed ID: 10068789
  Publication DOI: 10.1023/a:1001799711799
  Journal NLM ID: 0372625
  Publisher: Dordrecht: Kluwer Academic
  Correspondence: j.philp@napier.ac.uk
  Institutions: Technical University Braunschweig, Department of Biochemistry and Biotechnology, Biotechnology Group, Braunschweig, Germany, Napier University, Department of Biological Sciences, Edinburgh, UK
  
   
  
  Rhodococcus erythropolis DSM 43215
  CSDB ID 3248 (all data & tools)
• Article ID: 5669
  Rapp P, Bock H, Wray V, Wagner F "Formation, isolation and characterization of trehalose dimycolates from Rhodococcus erythropolis grown on n-alkanes" - Journal of General Microbiology 115(2) (1979) 491-503
  

  Rhodococcus erythropolis DSM 43215 produced a surface-active trehalose lipid whose formation was induced by n-alkanes to a maximum of 2.1 g/l in a 50 l batch culture on 2% (w/v) n-alkanes of chain length C12 to C18. The glycolipid was extracted from the biomass with n-hexane and was purified by repeated chromatography on silica gel. It contained α,α-trehalose as the sole non-reducing sugar. The lipid moiety was characterized by 13C nuclear magnetic resonance spectroscopy and mass spectrometry and consisted predominantly of saturated long-chain α-branched β-hydroxy fatty acids (mycolic acids) ranging from C32H64O3 to C38H76O3, of which C34H68O3 and C35H70O3 predominated. The molar ratio of trehalose to mycolic acids was 1:2. 13C nuclear magnetic resonance analysis of the O-hexamethyltrehalose obtained by saponification of the permethylated trehalose dimycolates revealed, with the aid of deuterium exchange, that the ester linkages of mycolic acids are to both primary alcohol groups at the C-6 and C-6’ positions of the trehalose

  glycolipids, Rhodococcus erythropolis, trehalose dimycolates

  Publication DOI: 10.1099/00221287-115-2-491
  Journal NLM ID: 0375371
  Institutions: Gesellschaft für Biotechnologische Forschung mbH, Lehrstuhl für Biochemie und Biotechnologie der Universität Braunschweig, Braunschweig, Germany
  Methods: 13C NMR, methylation, IR, TLC, acid hydrolysis, GLC, MS, extraction, acetylation, column chromatography, cell growth, precipitation, derivatization, evaporation, determination of oxygen
  
   
  
  Rhodococcus erythropolis DSM 43215
  CSDB ID 47824 (all data & tools)
• Article ID: 9240
  da Silva AF, Banat IM, Giachini AJ, Robl D "Fungal biosurfactants, from nature to biotechnological product: bioprospection, production and potential applications" - Bioprocess and Biosystems Engineering 44(10) (2021) 2003-2034
  

  Biosurfactants are in demand by the global market as natural commodities that can be added to commercial products or use in environmental applications. These biomolecules reduce the surface/interfacial tension between fluid phases and exhibit superior stability to chemical surfactants under different physico-chemical conditions. Biotechnological production of biosurfactants is still emerging. Fungi are promising producers of these molecules with unique chemical structures, such as sophorolipids, mannosylerythritol lipids, cellobiose lipids, xylolipids, polyol lipids and hydrophobins. In this review, we aimed to contextualize concepts related to fungal biosurfactant production and its application in industry and the environment. Concepts related to the thermodynamic and physico-chemical properties of biosurfactants are presented, which allows detailed analysis of their structural and application. Promising niches for isolating biosurfactant-producing fungi are presented, as well as screening methodologies are discussed. Finally, strategies related to process parameters and variables, simultaneous production, process optimization through statistical and genetic tools, downstream processing and some aspects of commercial products formulations are presented.

  biosurfactants, filamentous fungi, yeasts, screening, bioprocess, downstream

  NCBI PubMed ID: 34131819
  Publication DOI: 10.1007/s00449-021-02597-5
  Journal NLM ID: 101088505
  Publisher: Berlin, Germany: Springer-Verlag
  Correspondence: diogo.robl@ufsc.br
  Institutions: Department of Microbiology, Immunology and Parasitology, Federal University of Santa Catarina (UFSC), Florianópolis, Brazil, Bioprocess and Biotechnology Engineering Undergraduate Program, Federal University of Tocantins (UFT), Gurupi, Brazil, School of Biomedical Sciences, Faculty of Life and Health Sciences, Ulster University, Coleraine, UK
  
   
  
  (fungi)
  CSDB ID 40914 (all data & tools)

Show legend Show as text

Structure type: oligomer
Compound class: LOS
Contained glycoepitopes: IEDB_136044,IEDB_136105,IEDB_137472,IEDB_137477,IEDB_141794,IEDB_142488,IEDB_144998,IEDB_146664,IEDB_190606,IEDB_225177,IEDB_742521,IEDB_885823,IEDB_983931,SB_165,SB_166,SB_187,SB_192,SB_195,SB_7,SB_88

• Article ID: 648
  Gilleron M, Puzo G "Lipooligosaccharidic antigens from Mycobacterium kansasii and Mycobacterium gastri" - Glycoconjugate Journal 12 (1995) 298-308
  

  A set of Lipooligosaccharides (LOSs) has previously been characterized in M. gastri W471. The structure of the highly antigenic LOS (LOS-III) was elucidated and this molecule can unambiguously distinguish M. gastri from the opportunistic pathogen M. kansasii. In the present study, the structures of three other M. gastri W471 LOSs were determined by one-dimensional 1H NMR spectroscopy and gas liquid chromatography. They differ by the number of Xylp units and by the structure of the distal monosaccharide. The two dimensional (2D) NMR approach was successfully applied to the LOS antigen of M. kansasii to locate the acetyl and acyl substituents and to determine the anomeric configuration of the α-D-Fucp unit. The molecular specificity of anti-LOS-III antibodies was investigated and the LOS-III epitope was defined as the distal disaccharide: 3,6-dideoxy-4-C-(1,3-dimethoxy-4,5,6,7-tetrahydroxy-heptyl)-α-xylohexp-(1→3)-β-L-Xylp.

  structure, 2D NMR spectroscopy, lipooligosaccharide (LOS), Mycobacterium gastri LOS epitope, ELISA

  NCBI PubMed ID: 7496145
  Journal NLM ID: 8603310
  Publisher: Kluwer Academic Publishers
  Institutions: Laboratoire de Pharmacologie et de Toxicologie Fondamentales du Centre National de la Recherche Scientifique, Toulouse, France
  Methods: NMR-2D, FAB-MS, GC-MS, NMR, HPLC, EI-MS
  
   
  
  Mycobacterium gastri W471
  CSDB ID 423 (all data & tools)

Show legend Show as text

Structure type: oligomer
Compound class: LOS
Contained glycoepitopes: IEDB_136044,IEDB_136105,IEDB_137472,IEDB_137477,IEDB_141794,IEDB_142488,IEDB_144998,IEDB_146664,IEDB_190606,IEDB_225177,IEDB_742521,IEDB_885823,IEDB_983931,SB_165,SB_166,SB_187,SB_192,SB_195,SB_7,SB_88

• Article ID: 648
  Gilleron M, Puzo G "Lipooligosaccharidic antigens from Mycobacterium kansasii and Mycobacterium gastri" - Glycoconjugate Journal 12 (1995) 298-308
  

  A set of Lipooligosaccharides (LOSs) has previously been characterized in M. gastri W471. The structure of the highly antigenic LOS (LOS-III) was elucidated and this molecule can unambiguously distinguish M. gastri from the opportunistic pathogen M. kansasii. In the present study, the structures of three other M. gastri W471 LOSs were determined by one-dimensional 1H NMR spectroscopy and gas liquid chromatography. They differ by the number of Xylp units and by the structure of the distal monosaccharide. The two dimensional (2D) NMR approach was successfully applied to the LOS antigen of M. kansasii to locate the acetyl and acyl substituents and to determine the anomeric configuration of the α-D-Fucp unit. The molecular specificity of anti-LOS-III antibodies was investigated and the LOS-III epitope was defined as the distal disaccharide: 3,6-dideoxy-4-C-(1,3-dimethoxy-4,5,6,7-tetrahydroxy-heptyl)-α-xylohexp-(1→3)-β-L-Xylp.

  structure, 2D NMR spectroscopy, lipooligosaccharide (LOS), Mycobacterium gastri LOS epitope, ELISA

  NCBI PubMed ID: 7496145
  Journal NLM ID: 8603310
  Publisher: Kluwer Academic Publishers
  Institutions: Laboratoire de Pharmacologie et de Toxicologie Fondamentales du Centre National de la Recherche Scientifique, Toulouse, France
  Methods: NMR-2D, FAB-MS, GC-MS, NMR, HPLC, EI-MS
  
   
  
  Mycobacterium gastri W471
  CSDB ID 556 (all data & tools)

Show legend Show as text

Structure type: oligomer
Compound class: LOS
Contained glycoepitopes: IEDB_136044,IEDB_136105,IEDB_137472,IEDB_137477,IEDB_141794,IEDB_142488,IEDB_144998,IEDB_146664,IEDB_190606,IEDB_225177,IEDB_742521,IEDB_885823,IEDB_983931,SB_165,SB_166,SB_187,SB_192,SB_195,SB_7,SB_88

• Article ID: 648
  Gilleron M, Puzo G "Lipooligosaccharidic antigens from Mycobacterium kansasii and Mycobacterium gastri" - Glycoconjugate Journal 12 (1995) 298-308
  

  A set of Lipooligosaccharides (LOSs) has previously been characterized in M. gastri W471. The structure of the highly antigenic LOS (LOS-III) was elucidated and this molecule can unambiguously distinguish M. gastri from the opportunistic pathogen M. kansasii. In the present study, the structures of three other M. gastri W471 LOSs were determined by one-dimensional 1H NMR spectroscopy and gas liquid chromatography. They differ by the number of Xylp units and by the structure of the distal monosaccharide. The two dimensional (2D) NMR approach was successfully applied to the LOS antigen of M. kansasii to locate the acetyl and acyl substituents and to determine the anomeric configuration of the α-D-Fucp unit. The molecular specificity of anti-LOS-III antibodies was investigated and the LOS-III epitope was defined as the distal disaccharide: 3,6-dideoxy-4-C-(1,3-dimethoxy-4,5,6,7-tetrahydroxy-heptyl)-α-xylohexp-(1→3)-β-L-Xylp.

  structure, 2D NMR spectroscopy, lipooligosaccharide (LOS), Mycobacterium gastri LOS epitope, ELISA

  NCBI PubMed ID: 7496145
  Journal NLM ID: 8603310
  Publisher: Kluwer Academic Publishers
  Institutions: Laboratoire de Pharmacologie et de Toxicologie Fondamentales du Centre National de la Recherche Scientifique, Toulouse, France
  Methods: NMR-2D, FAB-MS, GC-MS, NMR, HPLC, EI-MS
  
   
  
  Mycobacterium gastri W471
  CSDB ID 557 (all data & tools)

Show legend Show as text

Structure type: oligomer
Compound class: glycolipid
Contained glycoepitopes: IEDB_130698,IEDB_141181,IEDB_141806,IEDB_142488,IEDB_144998,IEDB_146664,IEDB_153543,IEDB_176772,IEDB_742521,IEDB_983931,SB_192

• Article ID: 741
  Khoo K, Suzuki R, Morris HR, Dell A, Brennan PJ, Besra GS "Structural definition of the glycopeptidolipids and the pyruvylated, glycosylated acyltrehalose from Mycobacterium butyricum" - Carbohydrate Research 276(2) (1995) 449-455
  

  no abstract

  structural analysis, glycopeptidolipids, pyruvylated, glycosylated acyltrehalose, Mycobacterium butyricum

  NCBI PubMed ID: 8542612
  Journal NLM ID: 0043535
  Publisher: Elsevier
  Institutions: Department of Biochemistry, Imperial College of Science, Technology and Medicine, London SW7 2A K UK, Department of Microbiology, Colorado State University, Fort Colins, CO, USA
  Methods: 1H NMR, GLC-MS, FAB-MS, GC-MS, TLC, GLC, composition analysis
  
   
  
  Mycobacterium butyricum ATCC 19979, Mycobacterium butyricum 559
  CSDB ID 879 (all data & tools)

Show legend Show as text

Structure type: oligomer
Contained glycoepitopes: IEDB_142488,IEDB_144998,IEDB_146664,IEDB_232584,IEDB_742521,IEDB_983931,SB_192

• Article ID: 1676
  Hisamatsu M, Yamada T, Akaki M, Nashinoki H, Takai Y, Amemura A "Structural studies on new, non-reducing oligosaccharides produced by Rhizobium meliloti J7017" - Agricultural and Biological Chemistry 49(5) (1985) 1447-1451
  

  Three non-reducing oligosaccharides were isolated from the fraction of cyclic (1-2)-β-Dglucan of Rhizobium meliloti J7017 by reversed-phase chromatography and paper chromatography. Methylation and 1H-NMR analyses indicated that they were α-D-glucopyranosyl α-kojitrioside, α-D-glucopyranosyl α-kojitetraoside, and α-D-glucopyranosyl α-kojipentaoside.

  Publication DOI: 10.1080/00021369.1985.10866904
  Journal NLM ID: 0370452
  Publisher: Tokyo: Agricultural Chemical Society Of Japan
  Institutions: Department of Agricultural Chemistry, Faculty of Agriculture, Mie University, Tsu, Japan
  
   
  
  Rhizobium meliloti J7017
  CSDB ID 101193 (all data & tools)

Show legend Show as text

Structure type: oligomer
Contained glycoepitopes: IEDB_142488,IEDB_144998,IEDB_146664,IEDB_232584,IEDB_742521,IEDB_983931,SB_192

• Article ID: 1676
  Hisamatsu M, Yamada T, Akaki M, Nashinoki H, Takai Y, Amemura A "Structural studies on new, non-reducing oligosaccharides produced by Rhizobium meliloti J7017" - Agricultural and Biological Chemistry 49(5) (1985) 1447-1451
  

  Three non-reducing oligosaccharides were isolated from the fraction of cyclic (1-2)-β-Dglucan of Rhizobium meliloti J7017 by reversed-phase chromatography and paper chromatography. Methylation and 1H-NMR analyses indicated that they were α-D-glucopyranosyl α-kojitrioside, α-D-glucopyranosyl α-kojitetraoside, and α-D-glucopyranosyl α-kojipentaoside.

  Publication DOI: 10.1080/00021369.1985.10866904
  Journal NLM ID: 0370452
  Publisher: Tokyo: Agricultural Chemical Society Of Japan
  Institutions: Department of Agricultural Chemistry, Faculty of Agriculture, Mie University, Tsu, Japan
  
   
  
  Rhizobium meliloti J7017
  CSDB ID 101194 (all data & tools)

Show legend Show as text

Structure type: oligomer
Contained glycoepitopes: IEDB_142488,IEDB_144998,IEDB_146664,IEDB_232584,IEDB_742521,IEDB_983931,SB_192

• Article ID: 1676
  Hisamatsu M, Yamada T, Akaki M, Nashinoki H, Takai Y, Amemura A "Structural studies on new, non-reducing oligosaccharides produced by Rhizobium meliloti J7017" - Agricultural and Biological Chemistry 49(5) (1985) 1447-1451
  

  Three non-reducing oligosaccharides were isolated from the fraction of cyclic (1-2)-β-Dglucan of Rhizobium meliloti J7017 by reversed-phase chromatography and paper chromatography. Methylation and 1H-NMR analyses indicated that they were α-D-glucopyranosyl α-kojitrioside, α-D-glucopyranosyl α-kojitetraoside, and α-D-glucopyranosyl α-kojipentaoside.

  Publication DOI: 10.1080/00021369.1985.10866904
  Journal NLM ID: 0370452
  Publisher: Tokyo: Agricultural Chemical Society Of Japan
  Institutions: Department of Agricultural Chemistry, Faculty of Agriculture, Mie University, Tsu, Japan
  
   
  
  Rhizobium meliloti J7017
  CSDB ID 101195 (all data & tools)

Show legend Show as text

Structure type: oligomer
Compound class: LOS
Contained glycoepitopes: IEDB_142488,IEDB_144998,IEDB_146664,IEDB_742521,IEDB_983931,SB_192

• Article ID: 1690
  Brennan PJ, Nikaido H "The envelope of mycobacteria" - Annual Review of Biochemistry 64 (1995) 29-63
  

  Mycobacteria, members of which cause tuberculosis and leprosy, produce cell walls of unusually low permeability, which contribute to their resistance to therapeutic agents. Their cell walls contain large amounts of C60-C90 fatty acids, mycolic acids, that are covalently linked to arabinogalactan. Recent studies clarified the unusual structures of arabinogalactan as well as of extractable cell wall lipids, such as trehalose-based lipooligosaccharides, phenolic glycolipids, and glycopeptidolipids. Most of the hydrocarbon chains of these lipids assemble to produce an asymmetric bilayer of exceptional thickness. Structural considerations suggest that the fluidity is exceptionally low in the innermost part of bilayer, gradually increasing toward the outer surface. Differences in mycolic acid structure may affect the fluidity and permeability of the bilayer, and may explain the different sensitivity levels of various mycobacterial species to lipophilic inhibitors. Hydrophilic nutrients and inhibitors, in contrast, traverse the cell wall presumably through channels of recently discovered porins.

  NCBI PubMed ID: 7574484
  Journal NLM ID: 2985150R
  Institutions: Department of Microbiology, Colorado State University, Fort Collins 80523, USA
  
   
  
  Mycobacterium smegmatis
  CSDB ID 103791 (all data & tools)

Show legend Show as text

Structure type: oligomer
Compound class: LOS
Contained glycoepitopes: IEDB_142488,IEDB_144998,IEDB_146664,IEDB_742521,IEDB_983931,SB_192

• Article ID: 1690
  Brennan PJ, Nikaido H "The envelope of mycobacteria" - Annual Review of Biochemistry 64 (1995) 29-63
  

  Mycobacteria, members of which cause tuberculosis and leprosy, produce cell walls of unusually low permeability, which contribute to their resistance to therapeutic agents. Their cell walls contain large amounts of C60-C90 fatty acids, mycolic acids, that are covalently linked to arabinogalactan. Recent studies clarified the unusual structures of arabinogalactan as well as of extractable cell wall lipids, such as trehalose-based lipooligosaccharides, phenolic glycolipids, and glycopeptidolipids. Most of the hydrocarbon chains of these lipids assemble to produce an asymmetric bilayer of exceptional thickness. Structural considerations suggest that the fluidity is exceptionally low in the innermost part of bilayer, gradually increasing toward the outer surface. Differences in mycolic acid structure may affect the fluidity and permeability of the bilayer, and may explain the different sensitivity levels of various mycobacterial species to lipophilic inhibitors. Hydrophilic nutrients and inhibitors, in contrast, traverse the cell wall presumably through channels of recently discovered porins.

  NCBI PubMed ID: 7574484
  Journal NLM ID: 2985150R
  Institutions: Department of Microbiology, Colorado State University, Fort Collins 80523, USA
  
   
  
  Mycobacterium fortuitum bv. fortuitum
  CSDB ID 103793 (all data & tools)

Show legend Show as text

Structure type: oligomer
Compound class: LOS
Contained glycoepitopes: IEDB_136045,IEDB_136098,IEDB_136105,IEDB_142488,IEDB_142489,IEDB_144562,IEDB_144998,IEDB_146664,IEDB_152214,IEDB_174333,IEDB_189517,IEDB_225177,IEDB_742521,IEDB_885823,IEDB_983931,SB_192,SB_86

• Article ID: 1759
  Daffé M, McNeil M, Brennan PJ "Novel type-specific lipooligosaccharides from Mycobacterium tuberculosis" - Biochemistry 30(2) (1991) 378-388
  

  Mycobacterium tuberculosis (strain Canetti) is characterized by the presence of two novel glycolipids of the alkali-labile, trehalose-containing lipooligosaccharide class. Their structures were established by permethylation, partial acid hydrolysis, infrared and high-field NMR spectroscopy, and electron-impact and fast atom bombardment mass spectrometry of the native glycolipids and hydrolysis products. The trehalose substituent is unique in that it is methylated at the 6'-position. The structure of the simpler of the two glycolipids is 2-O-Me-α-L-Fucp(1→3)-β-D-Glcp(1→3)-2-O-Me-α-L-Rhap(1→3)-2-O-Me-α-L-Rhap(1→3)-β-D-Glcp(1→3)-4-O-Me-α-L-Rhap(1→3)-6-O-Me-α-D-Glc. Further glycosylation of the octaglycosyl unit of this nonantigenic glycolipid by an incompletely defined N-acyl derivative of a 4-amino-4,6-dideoxy-Galp residue results in the second, highly antigenic nonasaccharide-containing glycolipid. Application of two-dimensional proton correlation spectroscopy demonstrated that the fatty acyl substituents are located on the 2,3,6 and 3,4,6 hydroxyl groups of the terminal glucosyl unit in the proportions of 2:3. Gas chromatography/mass spectrometry and optical rotation measurement allowed identification of the fatty acyl esters as primarily 2L-, 4L-dimethylhexadecanoate, 2L-,4L-,6L-,8L-tetramethyloctadecanoate, and 2-methyl-3-hydroxyeicosanoate. The relationship of these glycolipids to different morphological forms of M. tuberculosis and to virulence is discussed.

  NCBI PubMed ID: 1899023
  Journal NLM ID: 0370623
  Publisher: American Chemical Society
  Institutions: Department of Microbiology, Colorado State University, Fort Collins 80523
  
   
  
  Mycobacterium tuberculosis
  CSDB ID 107651 (all data & tools)

Show legend Show as text

Structure type: oligomer
Compound class: LOS
Contained glycoepitopes: IEDB_114701,IEDB_136105,IEDB_142488,IEDB_144998,IEDB_146664,IEDB_167188,IEDB_174332,IEDB_189517,IEDB_225177,IEDB_742521,IEDB_885823,IEDB_983931,SB_192

• Article ID: 1772
  Besra GS, McNeil MR, Khoo KH, Dell A, Morris HR, Brennan PJ "Trehalose-containing lipooligosaccharides of Mycobacterium gordonae: Presence of a mono-O-methyltetra-O-acyltrehalose "core" and branching in the oligosaccharide backbone" - Biochemistry 32(47) (1993) 12705-12714
  

  Past evidence has indicated that Mycobacterium gordonae, as isolated from soil and as an occasional opportunistic pathogen, exists as a serocomplex. We now demonstrate that the basis of seroreactivity and diversity is a novel series of alkali-labile, trehalose-containing lipooligosaccharides (LOS). The structures from two strains were established by per-O-methylation, partial acid hydrolysis, infrared and high-field NMR spectroscopy, electron-impact MS, and fast atom bombardment/mass spectrometry of the native lipooligosaccharides and hydrolysis products. The structure of the major lipooligosaccharide, LOS-I, of M. gordonae strain 989 was defined as 2-O-CH3-4-O-CH3CO-α-L-Fucp-(1→3)-β-D-Glcp-(1→3)-2-O-CH3-α-L-Rhap-(1→3)-[β-D-Xylp-(1→2)-]-α-L-Rhap-(1→3)-β-D-Glcp-(1→3)-α-L-Rhap-(1→3)-6-O-CH3-α-D-Glcp-(1<→1)-2,3,4,6-tetra-O-acyl-α-D-Glcp, which was further glycosylated at C-3 of the terminal 2-O-CH3-4-O-CH3CO-α-L-Fucp by an incompletely defined N-acyl derivative of 4-amino-4,6-dideoxy-2,3-di-O-CH3-Galp. The structure of the major lipooligosaccharide, LOS-I, of a second strain of M. gordonae (strain 990) was defined as α-L-Rhap-(1→2)-3-O-CH3-α-L-Rhap-(1→3)-[β-D-Xylp-(1→2)-]-α-L-Rhap-(1→3)-β-D-Glcp-(1→3)[β-D-Xylp-(1→2)-]-α-L-Rhap-(1→3)-β-D-Glcp-(1→3)-β-D-Glcp-(1→3)-α-L-Rhap-(1→3)-6-O-CH3-α-D-Glcp-(1<→1)-2,3,4,6-tetra-O-acyl-α-D-Glcp. The other minor LOSs from both strains were also defined. Both families of LOSs from the two strains contain a novel mono-6'-O-CH3-2,3,4,6-tetra-O-acyltrehalose unit, representing the first example of such a unit among the LOSs isolated to date from mycobacteria. Also, the more polar antigenic products, LOS-I, -II', -II", and -III from M. gordonae 989 and LOS-I, -II, and -II' from M. gordonae 990, are characterized by branching of the oligosaccharide backbone, the first instance of sugar branching in these products. In the case of LOS-I and -III from M. gordonae 989, the branch consists of a terminal (t)-β-D-Xylp unit, whereas in LOS-II' and -II", they are (t)-3-O-CH3-β-D-Xylp and (t)-α-D-Araf, respectively.(ABSTRACT TRUNCATED AT 400 WORDS)

  NCBI PubMed ID: 8251490
  Publication DOI: 10.1021/bi00210a020
  Journal NLM ID: 0370623
  Publisher: American Chemical Society
  Institutions: Department of Microbiology, Colorado State University, Fort Collins 80523
  Methods: 1H NMR, FAB-MS, TLC, FTIR, EI-MS
  
   
  
  Mycobacterium gordonae 989
  CSDB ID 107990 (all data & tools)

Show legend Show as text

Structure type: oligomer
Compound class: LOS
Contained glycoepitopes: IEDB_114701,IEDB_133754,IEDB_136105,IEDB_137477,IEDB_142488,IEDB_144998,IEDB_146664,IEDB_153543,IEDB_167188,IEDB_174332,IEDB_189517,IEDB_225177,IEDB_742521,IEDB_885823,IEDB_983931,SB_192

• Article ID: 1772
  Besra GS, McNeil MR, Khoo KH, Dell A, Morris HR, Brennan PJ "Trehalose-containing lipooligosaccharides of Mycobacterium gordonae: Presence of a mono-O-methyltetra-O-acyltrehalose "core" and branching in the oligosaccharide backbone" - Biochemistry 32(47) (1993) 12705-12714
  

  Past evidence has indicated that Mycobacterium gordonae, as isolated from soil and as an occasional opportunistic pathogen, exists as a serocomplex. We now demonstrate that the basis of seroreactivity and diversity is a novel series of alkali-labile, trehalose-containing lipooligosaccharides (LOS). The structures from two strains were established by per-O-methylation, partial acid hydrolysis, infrared and high-field NMR spectroscopy, electron-impact MS, and fast atom bombardment/mass spectrometry of the native lipooligosaccharides and hydrolysis products. The structure of the major lipooligosaccharide, LOS-I, of M. gordonae strain 989 was defined as 2-O-CH3-4-O-CH3CO-α-L-Fucp-(1→3)-β-D-Glcp-(1→3)-2-O-CH3-α-L-Rhap-(1→3)-[β-D-Xylp-(1→2)-]-α-L-Rhap-(1→3)-β-D-Glcp-(1→3)-α-L-Rhap-(1→3)-6-O-CH3-α-D-Glcp-(1<→1)-2,3,4,6-tetra-O-acyl-α-D-Glcp, which was further glycosylated at C-3 of the terminal 2-O-CH3-4-O-CH3CO-α-L-Fucp by an incompletely defined N-acyl derivative of 4-amino-4,6-dideoxy-2,3-di-O-CH3-Galp. The structure of the major lipooligosaccharide, LOS-I, of a second strain of M. gordonae (strain 990) was defined as α-L-Rhap-(1→2)-3-O-CH3-α-L-Rhap-(1→3)-[β-D-Xylp-(1→2)-]-α-L-Rhap-(1→3)-β-D-Glcp-(1→3)[β-D-Xylp-(1→2)-]-α-L-Rhap-(1→3)-β-D-Glcp-(1→3)-β-D-Glcp-(1→3)-α-L-Rhap-(1→3)-6-O-CH3-α-D-Glcp-(1<→1)-2,3,4,6-tetra-O-acyl-α-D-Glcp. The other minor LOSs from both strains were also defined. Both families of LOSs from the two strains contain a novel mono-6'-O-CH3-2,3,4,6-tetra-O-acyltrehalose unit, representing the first example of such a unit among the LOSs isolated to date from mycobacteria. Also, the more polar antigenic products, LOS-I, -II', -II", and -III from M. gordonae 989 and LOS-I, -II, and -II' from M. gordonae 990, are characterized by branching of the oligosaccharide backbone, the first instance of sugar branching in these products. In the case of LOS-I and -III from M. gordonae 989, the branch consists of a terminal (t)-β-D-Xylp unit, whereas in LOS-II' and -II", they are (t)-3-O-CH3-β-D-Xylp and (t)-α-D-Araf, respectively.(ABSTRACT TRUNCATED AT 400 WORDS)

  NCBI PubMed ID: 8251490
  Publication DOI: 10.1021/bi00210a020
  Journal NLM ID: 0370623
  Publisher: American Chemical Society
  Institutions: Department of Microbiology, Colorado State University, Fort Collins 80523
  Methods: 1H NMR, FAB-MS, TLC, FTIR, EI-MS
  
   
  
  Mycobacterium gordonae 990
  CSDB ID 107991 (all data & tools)

Show legend Show as text

Structure type: oligomer
Compound class: LOS
Contained glycoepitopes: IEDB_114701,IEDB_136045,IEDB_136105,IEDB_142488,IEDB_142489,IEDB_144562,IEDB_144998,IEDB_146664,IEDB_152214,IEDB_167188,IEDB_174332,IEDB_174333,IEDB_189517,IEDB_225177,IEDB_742521,IEDB_885823,IEDB_983931,SB_192,SB_86

• Article ID: 1772
  Besra GS, McNeil MR, Khoo KH, Dell A, Morris HR, Brennan PJ "Trehalose-containing lipooligosaccharides of Mycobacterium gordonae: Presence of a mono-O-methyltetra-O-acyltrehalose "core" and branching in the oligosaccharide backbone" - Biochemistry 32(47) (1993) 12705-12714
  

  Past evidence has indicated that Mycobacterium gordonae, as isolated from soil and as an occasional opportunistic pathogen, exists as a serocomplex. We now demonstrate that the basis of seroreactivity and diversity is a novel series of alkali-labile, trehalose-containing lipooligosaccharides (LOS). The structures from two strains were established by per-O-methylation, partial acid hydrolysis, infrared and high-field NMR spectroscopy, electron-impact MS, and fast atom bombardment/mass spectrometry of the native lipooligosaccharides and hydrolysis products. The structure of the major lipooligosaccharide, LOS-I, of M. gordonae strain 989 was defined as 2-O-CH3-4-O-CH3CO-α-L-Fucp-(1→3)-β-D-Glcp-(1→3)-2-O-CH3-α-L-Rhap-(1→3)-[β-D-Xylp-(1→2)-]-α-L-Rhap-(1→3)-β-D-Glcp-(1→3)-α-L-Rhap-(1→3)-6-O-CH3-α-D-Glcp-(1<→1)-2,3,4,6-tetra-O-acyl-α-D-Glcp, which was further glycosylated at C-3 of the terminal 2-O-CH3-4-O-CH3CO-α-L-Fucp by an incompletely defined N-acyl derivative of 4-amino-4,6-dideoxy-2,3-di-O-CH3-Galp. The structure of the major lipooligosaccharide, LOS-I, of a second strain of M. gordonae (strain 990) was defined as α-L-Rhap-(1→2)-3-O-CH3-α-L-Rhap-(1→3)-[β-D-Xylp-(1→2)-]-α-L-Rhap-(1→3)-β-D-Glcp-(1→3)[β-D-Xylp-(1→2)-]-α-L-Rhap-(1→3)-β-D-Glcp-(1→3)-β-D-Glcp-(1→3)-α-L-Rhap-(1→3)-6-O-CH3-α-D-Glcp-(1<→1)-2,3,4,6-tetra-O-acyl-α-D-Glcp. The other minor LOSs from both strains were also defined. Both families of LOSs from the two strains contain a novel mono-6'-O-CH3-2,3,4,6-tetra-O-acyltrehalose unit, representing the first example of such a unit among the LOSs isolated to date from mycobacteria. Also, the more polar antigenic products, LOS-I, -II', -II", and -III from M. gordonae 989 and LOS-I, -II, and -II' from M. gordonae 990, are characterized by branching of the oligosaccharide backbone, the first instance of sugar branching in these products. In the case of LOS-I and -III from M. gordonae 989, the branch consists of a terminal (t)-β-D-Xylp unit, whereas in LOS-II' and -II", they are (t)-3-O-CH3-β-D-Xylp and (t)-α-D-Araf, respectively.(ABSTRACT TRUNCATED AT 400 WORDS)

  NCBI PubMed ID: 8251490
  Publication DOI: 10.1021/bi00210a020
  Journal NLM ID: 0370623
  Publisher: American Chemical Society
  Institutions: Department of Microbiology, Colorado State University, Fort Collins 80523
  Methods: 1H NMR, FAB-MS, TLC, FTIR, EI-MS
  
   
  
  Mycobacterium gordonae 989
  CSDB ID 107992 (all data & tools)