Found 10 structures.
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1. Compound ID: 4785
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a-L-Fucp2Me3Me4Me-(1-3)-a-L-Rhap-(1-3)-a-L-Rhap-(1--/Phenolphthiocerol dimycocerosate/ |
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Structure type: oligomer
Aglycon: Phenolphthiocerol dimycocerosate
Compound class: glycolipid
Contained glycoepitopes: IEDB_130699,IEDB_136045,IEDB_136105,IEDB_142489,IEDB_144562,IEDB_151530,IEDB_152214,IEDB_174333,IEDB_225177,IEDB_885823,SB_86
The structure is contained in the following publication(s):
- Article ID: 1790
Daffé M "Further specific triglycosyl phenol phthiocerol diester from Mycobacterium tuberculosis" -
Biochimica et Biophysica Acta 1002 (1989) 257-260
Journal NLM ID: 0217513Publisher: Elsevier
Methods: 1H NMR
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2. Compound ID: 4791
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a-L-Fucp2Me3Me4Me-(1-3)-a-L-Rhap-(1-3)-a-L-Rhap2Me-(1--/phenolphthiotriol A dimycocerosate/ |
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Structure type: oligomer
Aglycon: phenolphthiotriol A dimycocerosate
Contained glycoepitopes: IEDB_130699,IEDB_136045,IEDB_136105,IEDB_142489,IEDB_144562,IEDB_151530,IEDB_152214,IEDB_174333,IEDB_225177,IEDB_885823,SB_86
The structure is contained in the following publication(s):
- Article ID: 1795
Watanabe M, Yamada Y, Iguchi K, Minnikin DE "Structural elucidation of new phenolic glycolipids from Mycobacterium tuberculosis" -
Biochimica et Biophysica Acta 1210 (1994) 174-180
From one clinical isolate of Mycobacterium tuberculosis, two new phenolic glycolipids(PGLs) were obtained as its major PGLs. These were dimycocerosyl esters of 2,4-di-O-methyl-fucopyranosyl-(α1→3)-rhamnopyranosyl-(α1→3)-2-O-methyl-rhamnopyranosyl-(α1→)-phenolphthiocerol A and -phenolphthiotriol A, which were produced by this strain at a ratio of about 5:1. Another clinical isolate of this species was found to produce PGL-tb1 and its analogue, 2,3,4-tri-O-methyl-fucopyranosyl-(α1→3)-rhamnopyranosyl-(α1→3)-2-O-methyl-rhamnopyranosyl-(α1→)-phenolphthiotriol A at a ratio of about 1:3. The fact that different strains of M. tuberculosis produce chemically different PGLs as their major PGLs may be related to the diversity of virulence of the clinical isolates of M. tuberculosis.
NCBI PubMed ID: 8280767Journal NLM ID: 0217513Publisher: Elsevier
Institutions: Research Institute of BCG, Tokyo, Japan
Methods: 13C NMR, 1H NMR
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3. Compound ID: 4794
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a-L-Fucp2Me3Me4Me-(1-3)-a-L-Rhap-(1-3)-a-L-Rhap2Me-(1--/phenolphthiocerol dimycocerosate/ |
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Structure type: oligomer
Aglycon: phenolphthiocerol dimycocerosate
Trivial name: phenylethanoid glycoside
Contained glycoepitopes: IEDB_130699,IEDB_136045,IEDB_136105,IEDB_142489,IEDB_144562,IEDB_151530,IEDB_152214,IEDB_174333,IEDB_225177,IEDB_885823,SB_86
The structure is contained in the following publication(s):
- Article ID: 1796
Hartmann S, Minnikin DE, Mallet AI, Ridell M, Rigouts L, Portaels F "Fast atom bombardment mass spectrometry of mycobacterial phenolic glycolipids" -
Biological Mass Spectrometry 23 (1994) 362-368
Fast atom bombardment mass spectra were successfully recorded for intact glycosylphenolphthiocerol dimycocerosates (phenolic glycolipids, PGLs) from Mycobacterium kansasii, M. leprae, M. tuberculosis, M. marinum, M. bovis and M. haemophilum. Characteristic fragment ions from the loss of the oligosaccharide moiety and one of the long-chain multimethyl-branched mycocerosic acids were observed in most cases. A tandem mass spectrometric experiment was carried out on the PGL from M. tuberculosis, revealing the type of mycocerosic acids esterified to individual homologues. Mass spectra of homologues separated by reversed-phase high-performance liquid chromatography gave information on the substitution pattern in certain cases. The potential of matrix-assisted laser desorption ionization spectroscopy was demonstrated by a successful analysis of the PGL from M. tuberculosis.
NCBI PubMed ID: 8038230Journal NLM ID: 9102982Institutions: Department of Chemistry, The University, Newcastle upon Tyne, UK
Methods: FAB-MS
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4. Compound ID: 5590
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a-L-Fucp2Me3Me4Me-(1-3)-a-L-Rhap-(1-3)-a-L-Rhap2Me-(1--/unknown/ |
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Structure type: oligomer
Aglycon: unknown
Contained glycoepitopes: IEDB_130699,IEDB_136045,IEDB_136105,IEDB_142489,IEDB_144562,IEDB_151530,IEDB_152214,IEDB_174333,IEDB_225177,IEDB_885823,SB_86
The structure is contained in the following publication(s):
- Article ID: 2406
Daffé M, Lacave C, Lanéelle MA, Lanéelle G "Structure of the major triglycosyl phenol-pthiocerol of Mycobacterium tuberculosis (strain Canetti)" -
European Journal of Biochemistry 167 (1987) 155-160
Journal NLM ID: 0107600Publisher: Oxford, UK: Blackwell Science Ltd. on behalf of the Federation of European Biochemical Societies
Methods: 13C NMR, 1H NMR, EI-MS
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5. Compound ID: 5599
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a-L-Fucp2Me3Me4Me-(1-3)-a-Rhap-(1-3)-a-Rhap2Me-(1--/phenolphthiocerol dimycocerosate/ |
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Structure type: oligomer
Aglycon: phenolphthiocerol dimycocerosate
Compound class: glycolipid
Contained glycoepitopes: IEDB_130699,IEDB_136045,IEDB_136105,IEDB_1394181,IEDB_142489,IEDB_144562,IEDB_145010,IEDB_151530,IEDB_152214,IEDB_174333,IEDB_225177,IEDB_885823,SB_86
The structure is contained in the following publication(s):
- Article ID: 2419
Daffé M, Servin P "Scalar, dipolar-correlated and J-resolved 2D-NMR spectroscopy of the specific phenolic mycoside of Mycobacterium tuberculosis" -
European Journal of Biochemistry 185 (1989) 157-162
Journal NLM ID: 0107600Publisher: Oxford, UK: Blackwell Science Ltd. on behalf of the Federation of European Biochemical Societies
Methods: 1H NMR, NMR-2D
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6. Compound ID: 13390
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LIP-(1-23)-+
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a-L-Fucp2Me3Me4Me-(1-3)-a-L-Rhap-(1-3)-a-L-Rhap2Me-(1-1)-Subst-(31-1)-Me-(?--/common lipid core/
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LIP-(1-25)-+
Subst = SMILES C{31}C(O)C(C)CCCCC{25}(O)C{23}C(O)CCCCCCCCCCCCCCCCc1cc{1}c(O)cc1 |
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Structure type: oligomer
Aglycon: common lipid core
Compound class: glycolipid
Contained glycoepitopes: IEDB_130699,IEDB_136045,IEDB_136105,IEDB_142489,IEDB_144562,IEDB_151530,IEDB_152214,IEDB_174333,IEDB_225177,IEDB_885823,SB_86
The structure is contained in the following publication(s):
- Article ID: 5317
Constant P, Perez E, Malaga W, Lanéelle MA, Saurel O, Daffé M, Guilhot C "Role of the pks15/1 gene in the biosynthesis of phenolglycolipids in the Mycobacterium tuberculosis complex. Evidence that all strains synthesize glycosylated p-hydroxybenzoic methyl esters and that strains devoid of phenolglycolipids harbor a frameshift mutation in the pks15/1 gene" -
Journal of Biological Chemistry 277(41) (2002) 38148-38158
Diesters of phthiocerol and phenolphthiocerol are important virulence factors of Mycobacterium tuberculosis and Mycobacterium leprae, the two main mycobacterial pathogens in humans. They are both long-chain β-diols, and their biosynthetic pathway is beginning to be elucidated. Although the two classes of molecules share a common lipid core, phthiocerol diesters have been found in all the strains of the M. tuberculosis complex examined although phenolphthiocerol diesters are produced by only a few groups of strains. To address the question of the origin of this diversity 8 reference strains and 10 clinical isolates of M. tuberculosis were analyzed. We report the presence of glycosylated p-hydroxybenzoic acid methyl esters, structurally related to the type-specific phenolphthiocerol glycolipids, in the culture media of all reference strains of M. tuberculosis, suggesting that the strains devoid of phenolphthiocerol derivatives are unable to elongate the putative p-hydroxybenzoic acid precursor. We also show that all the strains of M. tuberculosis examined and deficient in the production of phenolphthiocerol derivatives are natural mutants with a frameshift mutation in pks15/1 whereas a single open reading frame for pks15/1 is found in Mycobacterium bovis BCG, M. leprae, and strains of M. tuberculosis that produce phenolphthiocerol derivatives. Complementation of the H37Rv strain of M. tuberculosis, which is devoid of phenolphthiocerol derivatives, with the fused pks15/1 gene from M. bovis BCG restored phenolphthiocerol glycolipids production. Conversely, disruption of the pks15/1 gene in M. bovis BCG led to the abolition of the synthesis of type-specific phenolphthiocerol glycolipid. These data indicate that Pks15/1 is involved in the elongation of p-hydroxybenzoic acid to give p-hydroxyphenylalkanoates, which in turn are converted, presumably by the PpsA-E synthase, to phenolphthiocerol derivatives.
Mycobacterium leprae, Mycobacterium tuberculosis, phthiocerol dimycocerosates, phenolglycolipid
NCBI PubMed ID: 12138124Publication DOI: 10.1074/jbc.M206538200Journal NLM ID: 2985121RPublisher: Baltimore, MD: American Society for Biochemistry and Molecular Biology
Correspondence: Daffé M
; Guilhot C
Institutions: Département ''Mécanismes Moléculaires des Infections Mycobactériennes'', Institut de Pharmacologie et Biologie Structurale, CNRS and Université Paul Sabatier (Unité Mixte de Recherche 5089), Toulouse Cedex, France
Methods: NMR-2D, IR, DNA sequencing, GC-MS, DNA techniques, GC, MALDI-TOF MS, methanolysis, UV, extraction, column chromatography, cell growth, derivatization, acylation
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7. Compound ID: 13392
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a-L-Fucp2Me3Me4Me-(1-3)-a-L-Rhap-(1-3)-a-L-Rhap2Me-(1-4)-4HOBz-(7-1)-Me |
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Structure type: monomer
Compound class: glycoside
Contained glycoepitopes: IEDB_130699,IEDB_136045,IEDB_136105,IEDB_142489,IEDB_144562,IEDB_151530,IEDB_152214,IEDB_174333,IEDB_225177,IEDB_885823,SB_86
The structure is contained in the following publication(s):
- Article ID: 5317
Constant P, Perez E, Malaga W, Lanéelle MA, Saurel O, Daffé M, Guilhot C "Role of the pks15/1 gene in the biosynthesis of phenolglycolipids in the Mycobacterium tuberculosis complex. Evidence that all strains synthesize glycosylated p-hydroxybenzoic methyl esters and that strains devoid of phenolglycolipids harbor a frameshift mutation in the pks15/1 gene" -
Journal of Biological Chemistry 277(41) (2002) 38148-38158
Diesters of phthiocerol and phenolphthiocerol are important virulence factors of Mycobacterium tuberculosis and Mycobacterium leprae, the two main mycobacterial pathogens in humans. They are both long-chain β-diols, and their biosynthetic pathway is beginning to be elucidated. Although the two classes of molecules share a common lipid core, phthiocerol diesters have been found in all the strains of the M. tuberculosis complex examined although phenolphthiocerol diesters are produced by only a few groups of strains. To address the question of the origin of this diversity 8 reference strains and 10 clinical isolates of M. tuberculosis were analyzed. We report the presence of glycosylated p-hydroxybenzoic acid methyl esters, structurally related to the type-specific phenolphthiocerol glycolipids, in the culture media of all reference strains of M. tuberculosis, suggesting that the strains devoid of phenolphthiocerol derivatives are unable to elongate the putative p-hydroxybenzoic acid precursor. We also show that all the strains of M. tuberculosis examined and deficient in the production of phenolphthiocerol derivatives are natural mutants with a frameshift mutation in pks15/1 whereas a single open reading frame for pks15/1 is found in Mycobacterium bovis BCG, M. leprae, and strains of M. tuberculosis that produce phenolphthiocerol derivatives. Complementation of the H37Rv strain of M. tuberculosis, which is devoid of phenolphthiocerol derivatives, with the fused pks15/1 gene from M. bovis BCG restored phenolphthiocerol glycolipids production. Conversely, disruption of the pks15/1 gene in M. bovis BCG led to the abolition of the synthesis of type-specific phenolphthiocerol glycolipid. These data indicate that Pks15/1 is involved in the elongation of p-hydroxybenzoic acid to give p-hydroxyphenylalkanoates, which in turn are converted, presumably by the PpsA-E synthase, to phenolphthiocerol derivatives.
Mycobacterium leprae, Mycobacterium tuberculosis, phthiocerol dimycocerosates, phenolglycolipid
NCBI PubMed ID: 12138124Publication DOI: 10.1074/jbc.M206538200Journal NLM ID: 2985121RPublisher: Baltimore, MD: American Society for Biochemistry and Molecular Biology
Correspondence: Daffé M
; Guilhot C
Institutions: Département ''Mécanismes Moléculaires des Infections Mycobactériennes'', Institut de Pharmacologie et Biologie Structurale, CNRS and Université Paul Sabatier (Unité Mixte de Recherche 5089), Toulouse Cedex, France
Methods: NMR-2D, IR, DNA sequencing, GC-MS, DNA techniques, GC, MALDI-TOF MS, methanolysis, UV, extraction, column chromatography, cell growth, derivatization, acylation
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8. Compound ID: 13536
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a-L-Fucp2Me3Me4Me-(1-3)-a-L-Rhap-(1-3)-a-L-Rhap2Me-(1-4)-4HOBz-(7-1)-Me |
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Structure type: oligomer
Contained glycoepitopes: IEDB_130699,IEDB_136045,IEDB_136105,IEDB_142489,IEDB_144562,IEDB_151530,IEDB_152214,IEDB_174333,IEDB_225177,IEDB_885823,SB_86
The structure is contained in the following publication(s):
- Article ID: 5384
Simeone R, Huet G, Constant P, Malaga W, Lemassu A, Laval F, Daffé M, Guilhot C, Chalut C "Functional characterisation of three o-methyltransferases involved in the biosynthesis of phenolglycolipids in Mycobacterium tuberculosis" -
PLoS One 8(3) (2013) e58954
Phenolic glycolipids are produced by a very limited number of slow-growing mycobacterial species, most of which are pathogen for humans. In Mycobacterium tuberculosis, the etiologic agent of tuberculosis, these molecules play a role in the pathogenicity by modulating the host immune response during infection. The major variant of phenolic glycolipids produced by M. tuberculosis, named PGL-tb, consists of a large lipid core terminated by a glycosylated aromatic nucleus. The carbohydrate part is composed of three sugar residues, two rhamnosyl units and a terminal fucosyl residue, which is per-O-methylated, and seems to be important for pathogenicity. While most of the genes responsible for the synthesis of the lipid core domain and the saccharide appendage of PGL-tb have been characterized, the enzymes involved in the O-methylation of the fucosyl residue of PGL-tb remain unknown. In this study we report the identification and characterization of the methyltransferases required for the O-methylation of the terminal fucosyl residue of PGL-tb. These enzymes are encoded by genes Rv2954c, Rv2955c and Rv2956. Mutants of M. tuberculosis harboring deletion within these genes were constructed. Purification and analysis of the phenolglycolipids produced by these strains, using a combination of mass spectrometry and NMR spectroscopy, revealed that Rv2954c, Rv2955c and Rv2956 encode the methyltransferases that respectively catalysed the O-methylation of the hydroxyl groups located at positions 3, 4 and 2 of the terminal fucosyl residue of PGL-tb. Our data also suggest that methylation at these positions is a sequential process, starting with position 2, followed by positions 4 and 3
gene, virulence, identification, complex, methylation, transposon mutagenesis, strains, smegmatis, bcg
NCBI PubMed ID: 23536839Publication DOI: 10.1371/journal.pone.0058954Journal NLM ID: 101285081Publisher: San Francisco, CA: Public Library of Science
Correspondence: Chalut C
Institutions: Centre national de la recherche scientifique, Institut de Pharmacologie et de Biologie Structurale, Toulouse, France, Université de Toulouse, Université Paul Sabatier, Institut de Pharmacologie et de Biologie Structurale, Toulouse, France
Methods: 13C NMR, 1H NMR, MALDI-TOF MS, MS
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9. Compound ID: 13537
|
a-L-Fucp2Me3Me4Me-(1-3)-a-L-Rhap-(1-1)-Subst
Subst = phenolphthiocerol dimycocerosate = SMILES CCCCCCCCCCCCCCCCCCCCC(C)CC(C)CC(C)CC(C)CC(C)C(=O)OC(CCCCC(C)C(C)OC)CC(CCCCCCCCCCCCCCCCc1ccc{1}(O)cc1)OC(=O)C(C)CC(C)CC(C)CC(C)CC(C)CCCCCCCCCCCCCCCCCCC |
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Structure type: oligomer
Contained glycoepitopes: IEDB_130699,IEDB_136045,IEDB_136105,IEDB_142489,IEDB_144562,IEDB_151530,IEDB_152214,IEDB_174333,IEDB_225177,IEDB_885823,SB_86
The structure is contained in the following publication(s):
- Article ID: 5384
Simeone R, Huet G, Constant P, Malaga W, Lemassu A, Laval F, Daffé M, Guilhot C, Chalut C "Functional characterisation of three o-methyltransferases involved in the biosynthesis of phenolglycolipids in Mycobacterium tuberculosis" -
PLoS One 8(3) (2013) e58954
Phenolic glycolipids are produced by a very limited number of slow-growing mycobacterial species, most of which are pathogen for humans. In Mycobacterium tuberculosis, the etiologic agent of tuberculosis, these molecules play a role in the pathogenicity by modulating the host immune response during infection. The major variant of phenolic glycolipids produced by M. tuberculosis, named PGL-tb, consists of a large lipid core terminated by a glycosylated aromatic nucleus. The carbohydrate part is composed of three sugar residues, two rhamnosyl units and a terminal fucosyl residue, which is per-O-methylated, and seems to be important for pathogenicity. While most of the genes responsible for the synthesis of the lipid core domain and the saccharide appendage of PGL-tb have been characterized, the enzymes involved in the O-methylation of the fucosyl residue of PGL-tb remain unknown. In this study we report the identification and characterization of the methyltransferases required for the O-methylation of the terminal fucosyl residue of PGL-tb. These enzymes are encoded by genes Rv2954c, Rv2955c and Rv2956. Mutants of M. tuberculosis harboring deletion within these genes were constructed. Purification and analysis of the phenolglycolipids produced by these strains, using a combination of mass spectrometry and NMR spectroscopy, revealed that Rv2954c, Rv2955c and Rv2956 encode the methyltransferases that respectively catalysed the O-methylation of the hydroxyl groups located at positions 3, 4 and 2 of the terminal fucosyl residue of PGL-tb. Our data also suggest that methylation at these positions is a sequential process, starting with position 2, followed by positions 4 and 3
gene, virulence, identification, complex, methylation, transposon mutagenesis, strains, smegmatis, bcg
NCBI PubMed ID: 23536839Publication DOI: 10.1371/journal.pone.0058954Journal NLM ID: 101285081Publisher: San Francisco, CA: Public Library of Science
Correspondence: Chalut C
Institutions: Centre national de la recherche scientifique, Institut de Pharmacologie et de Biologie Structurale, Toulouse, France, Université de Toulouse, Université Paul Sabatier, Institut de Pharmacologie et de Biologie Structurale, Toulouse, France
Methods: 13C NMR, 1H NMR, MALDI-TOF MS, MS
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10. Compound ID: 13541
|
a-L-Fucp2Me3Me4Me-(1-3)-a-L-Rhap-(1-3)-a-L-Rhap2Me-(1-1)-Subst
Subst = phenolphthiocerol dimycocerosate = SMILES CCCCCCCCCCCCCCCCCCCCC(C)CC(C)CC(C)CC(C)CC(C)C(=O)OC(CCCCC(C)C(C)OC)CC(CCCCCCCCCCCCCCCCc1ccc{1}(O)cc1)OC(=O)C(C)CC(C)CC(C)CC(C)CC(C)CCCCCCCCCCCCCCCCCCC |
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Structure type: oligomer
Contained glycoepitopes: IEDB_130699,IEDB_136045,IEDB_136105,IEDB_142489,IEDB_144562,IEDB_151530,IEDB_152214,IEDB_174333,IEDB_225177,IEDB_885823,SB_86
The structure is contained in the following publication(s):
- Article ID: 5384
Simeone R, Huet G, Constant P, Malaga W, Lemassu A, Laval F, Daffé M, Guilhot C, Chalut C "Functional characterisation of three o-methyltransferases involved in the biosynthesis of phenolglycolipids in Mycobacterium tuberculosis" -
PLoS One 8(3) (2013) e58954
Phenolic glycolipids are produced by a very limited number of slow-growing mycobacterial species, most of which are pathogen for humans. In Mycobacterium tuberculosis, the etiologic agent of tuberculosis, these molecules play a role in the pathogenicity by modulating the host immune response during infection. The major variant of phenolic glycolipids produced by M. tuberculosis, named PGL-tb, consists of a large lipid core terminated by a glycosylated aromatic nucleus. The carbohydrate part is composed of three sugar residues, two rhamnosyl units and a terminal fucosyl residue, which is per-O-methylated, and seems to be important for pathogenicity. While most of the genes responsible for the synthesis of the lipid core domain and the saccharide appendage of PGL-tb have been characterized, the enzymes involved in the O-methylation of the fucosyl residue of PGL-tb remain unknown. In this study we report the identification and characterization of the methyltransferases required for the O-methylation of the terminal fucosyl residue of PGL-tb. These enzymes are encoded by genes Rv2954c, Rv2955c and Rv2956. Mutants of M. tuberculosis harboring deletion within these genes were constructed. Purification and analysis of the phenolglycolipids produced by these strains, using a combination of mass spectrometry and NMR spectroscopy, revealed that Rv2954c, Rv2955c and Rv2956 encode the methyltransferases that respectively catalysed the O-methylation of the hydroxyl groups located at positions 3, 4 and 2 of the terminal fucosyl residue of PGL-tb. Our data also suggest that methylation at these positions is a sequential process, starting with position 2, followed by positions 4 and 3
gene, virulence, identification, complex, methylation, transposon mutagenesis, strains, smegmatis, bcg
NCBI PubMed ID: 23536839Publication DOI: 10.1371/journal.pone.0058954Journal NLM ID: 101285081Publisher: San Francisco, CA: Public Library of Science
Correspondence: Chalut C
Institutions: Centre national de la recherche scientifique, Institut de Pharmacologie et de Biologie Structurale, Toulouse, France, Université de Toulouse, Université Paul Sabatier, Institut de Pharmacologie et de Biologie Structurale, Toulouse, France
Methods: 13C NMR, 1H NMR, MALDI-TOF MS, MS
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