Found 7 structures.
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1. Compound ID: 828
Structure type: oligomer
Compound class: glycolipid
Contained glycoepitopes: IEDB_128162,IEDB_128164,IEDB_134625,IEDB_136105,IEDB_137477,IEDB_142488,IEDB_146664,IEDB_225177,IEDB_885823,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 227
Wu XM, Mariño-Albernas JR, Auzanneau FI, Verez-Bencomo V, Pinto BM "Synthesis and NMR analysis of 13C-labeled oligosaccharides corresponding to the major glycolipid from Mycobacterium leprae" -
Carbohydrate Research 306(4) (1998) 493-503
An improved synthesis of propyl 4-O-(3,6-di-O-methyl-b-D-glycopyranosyl)-2,3-di-O-methyl-a-L-rhamnopyranoside, a disaccharide corresponding to the phenolic glycolipid of Mycobacterium leprae using a trichloroacetimidate as a glycosyl donor is described. The synthetic strategy is also applied to the preparation of three corresponding disaccharide analogues containing 13C-labeled methyl groups. The preparation of the trisaccharide, propyl 2-O-[4-O-93.6-di_O-methyl-b-D-glucopyranosyl)-2,3-di-O-methyl-a-L-rhamnopyranosyl]-3-O-methyl-a-L-rhamnopyranoside is also reported. The di-and tri-saccharides were characterized by 1H and 13C NMR spectroscopy.
NMR, synthesis, oligosaccharide, analysis, Oligosaccharides, Mycobacterium, Mycobacteria, glycolipid, C-13-labeled, Mycobacterium leprae, NMR analysis, oligosaccharide haptens
NCBI PubMed ID: 9679274Journal NLM ID: 0043535Publisher: Elsevier
Institutions: Department of Chemistry, Simon Fraser University, Burnaby, B.C., Canada, V5A 1S6, Laboratory for Carbohydrate Chemistry, Fucltad de Quimica, Universidad de la Habana, Centro Nacional de Biopreparados, Ciudad Habana, Cuba
Methods: chemical methods
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2. Compound ID: 829
Structure type: oligomer
Contained glycoepitopes: IEDB_128162,IEDB_128163,IEDB_128164,IEDB_131183,IEDB_133754,IEDB_134625,IEDB_136105,IEDB_137477,IEDB_142488,IEDB_146664,IEDB_225177,IEDB_885823,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 227
Wu XM, Mariño-Albernas JR, Auzanneau FI, Verez-Bencomo V, Pinto BM "Synthesis and NMR analysis of 13C-labeled oligosaccharides corresponding to the major glycolipid from Mycobacterium leprae" -
Carbohydrate Research 306(4) (1998) 493-503
An improved synthesis of propyl 4-O-(3,6-di-O-methyl-b-D-glycopyranosyl)-2,3-di-O-methyl-a-L-rhamnopyranoside, a disaccharide corresponding to the phenolic glycolipid of Mycobacterium leprae using a trichloroacetimidate as a glycosyl donor is described. The synthetic strategy is also applied to the preparation of three corresponding disaccharide analogues containing 13C-labeled methyl groups. The preparation of the trisaccharide, propyl 2-O-[4-O-93.6-di_O-methyl-b-D-glucopyranosyl)-2,3-di-O-methyl-a-L-rhamnopyranosyl]-3-O-methyl-a-L-rhamnopyranoside is also reported. The di-and tri-saccharides were characterized by 1H and 13C NMR spectroscopy.
NMR, synthesis, oligosaccharide, analysis, Oligosaccharides, Mycobacterium, Mycobacteria, glycolipid, C-13-labeled, Mycobacterium leprae, NMR analysis, oligosaccharide haptens
NCBI PubMed ID: 9679274Journal NLM ID: 0043535Publisher: Elsevier
Institutions: Department of Chemistry, Simon Fraser University, Burnaby, B.C., Canada, V5A 1S6, Laboratory for Carbohydrate Chemistry, Fucltad de Quimica, Universidad de la Habana, Centro Nacional de Biopreparados, Ciudad Habana, Cuba
Methods: chemical methods
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3. Compound ID: 4466
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b-D-Glcp3Me6Me-(1-4)-a-L-Rhap2Me3Me-(1-2)-a-L-Rhap3Me-(1--/phenolphthiocerol dimycocerosate/ |
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Structure type: oligomer
Aglycon: phenolphthiocerol dimycocerosate
Compound class: glycolipid
Contained glycoepitopes: IEDB_128162,IEDB_128163,IEDB_128164,IEDB_131183,IEDB_133754,IEDB_134625,IEDB_136105,IEDB_137477,IEDB_142488,IEDB_146664,IEDB_225177,IEDB_885823,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 1685
Jardine I, Scanlan G, McNeil M, Brennan PJ "Plasma desorption mass spectrometric analysis of mycobacterial glycolipids" -
Analytical Chemistry 61 (1989) 416-422
Mycobacteria are characterized by species- or type-specific glycolipid antigens. These are generally of the following three types: the trehalose-containing, acylated lipooligosaccharides (LOS), the C-mycoside glycopeptidolipids (GPL), and the phenolic glycolipids (PGL). To date, convenient mass spectrometric analysis of the intact form of these complex glycolipids has proved to be difficult. The successful plasma desorption mass spectrometric analysis of intact mycobacterial glycolipids of the LOS, GPL, and PGL types is now reported, allowing location of the acyl residues and providing oligosaccharide sequence and molecular weight information.
NCBI PubMed ID: 2719255Publication DOI: 10.1021/ac00180a008Journal NLM ID: 0370536
- Article ID: 1791
Daffé M, Lanéelle MA "Diglycosyl phenol phthiocerol diester of Mycobacterium leprae" -
Biochimica et Biophysica Acta 1002 (1989) 333-337
Journal NLM ID: 0217513Publisher: Elsevier
Methods: 1H NMR
- 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: 4477
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b-D-Glcp3Me6Me-(1-4)-a-L-Rhap2Me3Me-(1-2)-a-L-Rhap3Me-(1--/(->4) Phenolphthiocerol dimycocerosate/ |
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Structure type: oligomer
Aglycon: (->4) Phenolphthiocerol dimycocerosate
Contained glycoepitopes: IEDB_128162,IEDB_128163,IEDB_128164,IEDB_131183,IEDB_133754,IEDB_134625,IEDB_136105,IEDB_137477,IEDB_142488,IEDB_146664,IEDB_225177,IEDB_885823,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 1691
Gaylord H, Brennan PJ "Leprosy and the leprosy bacillus: Recent developments in characterization of antigens and immunology of the disease" -
Annual Review of Microbiology 41 (1987) 645-675
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5. Compound ID: 5255
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b-D-Glcp3Me6Me-(1-4)-a-L-Rhap2Me3Me-(1-2)-a-L-Rhap3Me-(1-1)-Allyl |
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Structure type: oligomer
Contained glycoepitopes: IEDB_128162,IEDB_128163,IEDB_128164,IEDB_131183,IEDB_133754,IEDB_134625,IEDB_136105,IEDB_137477,IEDB_142488,IEDB_146664,IEDB_225177,IEDB_885823,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 2163
Bock K, Hvidt T, Marino-Albernas J, Verez-Bencomo V "An NMR and conformational analysis of the terminal trisaccharide from the serologically active glycolipid of Mycobacterium leprae in different solvents" -
Carbohydrate Research 200 (1990) 33-45
The 1H- and 13C-n.m.r. spectra of allyl 2-O-[4-O-(3,6-di-O-methyl-β-d-glucopyranosyl)-2,3-di-O-methyl-a-l-rhamnopyranosyl]-3-O-methyl-a-l- rhamnopyranoside (3), a glycoside of the terminal trisaccharide found in the phenolic glycolipid I from Mycobacterium leprae, and those of the two component disaccharides, allyl 4-O-(3,6-di-O-methyl-β-d-glucopyranosyl)-2,3-di-O-methyl-a-l-rhamnopyranoside (1) and allyl 2-O-(2,3-di-O-methyl-a-l-rhamnopyranosyl)-3-O-methyl-a-l-rhamnopyranoside (2) have been assigned completely by 1D and 2D techniques. The preferred conformations, determined by chemical shift and n.O.e. studies, were different in D2O, CD3OD, and CDCl3. The preferred conformation of 3 accorded with the results of hard-sphere exo-anomeric (HSEA) calculations.
Publication DOI: 10.1016/0008-6215(90)84180-3Journal NLM ID: 0043535Publisher: Elsevier
Institutions: Department of Chemistry, Carlsberg Laboratory, Gl. Carlsberg Vej 10, DK-2500 Valby Denmark, Department of Organic Chemistry, The Technical University of Denmark, DK-2800 Lyngby Denmark, Laboratory for Carbohydrate Chemistry, Facultad de Quimica, Universidad de la Habana, and Centro National de Biopreparados, Ciudad Habana Cuba
Methods: NMR, conformation analysis
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6. Compound ID: 5910
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b-D-Glcp3Me6Me-(1-4)-a-L-Rhap2Me3Me-(1-2)-a-L-Rhap3Me-(1--/Phenol/ |
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Structure type: oligomer
Aglycon: Phenol
Trivial name: phenolic glycolipid-I
Contained glycoepitopes: IEDB_128162,IEDB_128163,IEDB_128164,IEDB_131183,IEDB_133754,IEDB_134625,IEDB_136105,IEDB_137477,IEDB_142488,IEDB_146664,IEDB_225177,IEDB_885823,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 2630
Hunter SW, Fujiwara T, Brennan PJ "Structure and antigenicity of the major specific glycolipid antigen of Mycobacterium leprae" -
Journal of Biological Chemistry 257 (1982) 15072-15078
Earlier we reported on the presence of a specific phenolic glycolipid (Phenolic Glycolipid-I) in Mycobacterium leprae, and in infected armadillo tissues (Hunter, S. W., and Brennan, P. J. (1981) J. Bacteriol. 147, 728-735). It had an inherent oligosaccharide, composed of 3-O-Me-rhamnose, 2,3-di-O-Me-rhamnose, and 3,6-di-O-Me-glucose, glycosidically linked to the phenol substituent. The structure of the oligosaccharide has now been determined, by partial acid hydrolysis, permethylation, 1H NMR, and 13C NMR as: 3,6-di-O-Me-Glcp(1β→4)2,3-di-O-Me-Rhap(1α→2)3-O-Me-Rhap(1α→phenol (assuming that the glucose substituent is in the D-enantiomeric configuration, and the two methylated rhamnoses are L). Acid hydrolysis of deacylated Phenolic glycolipid-I yielded a phenolic phthiocerol "core," and mass spectrometry and proton NMR of the permethylated core suggested the following structure: (structure: see text) Combined gas-liquid chromatography-mass spectrometry showed three tetramethyl branched "mycocerosic" acids, C30, C32 and C34, with molecular weights (as methyl esters) of 466, 494, and 522, respectively. These are esterified to the hydroxyl functions of the branched glycolic chain. Evidence is also presented that the glycolipid is immunologically active, reacting with rabbit antisera to M. leprae and with sera from lepromatous leprosy patients.
NCBI PubMed ID: 6184369Journal NLM ID: 2985121RPublisher: Baltimore, MD: American Society for Biochemistry and Molecular Biology
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7. Compound ID: 12203
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b-D-Glcp3Me6Me-(1-4)-a-L-Rhap2Me3Me-(1-2)-a-L-Rhap3Me-(1--/phenolic lipid/ |
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Structure type: oligomer
Aglycon: phenolic lipid
Trivial name: PGL-I
Compound class: glycolipid
Contained glycoepitopes: IEDB_128162,IEDB_128163,IEDB_128164,IEDB_131183,IEDB_133754,IEDB_134625,IEDB_136105,IEDB_137477,IEDB_142488,IEDB_146664,IEDB_225177,IEDB_885823,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 4852
Kondakov NN, Melnikova TM, Chekryzhova TV, Melnikova MV, Zinin AI, Torgov VI, Chizhov AO, Kononov LO "Synthesis of a disaccharide of phenolic glycolipid from Mycobacterium leprae (PGL-I) and its conjugates with bovine serum albumin" -
Russian Chemical Bulletin = Izvestiia Akademii nauk. Seriia khimicheskaia 64(5) (2015) 1142-1148
Terminal disaccharide fragment of phenolic glycolipid from Mycobacterium leprae (PGL-I) was synthesized as a glycoside with 4-(2-aminoethoxy)phenyl aglycon. The obtained 4-(2-aminoethoxy)phenyl 4-O-(3,6-di-O-methyl-β-d-glucopyranosyl)-2,3-di-O-methyl-α-l-rhamnopyranoside was used for the synthesis of a series of neoglycoconjugates with bovine serum albumin with different degrees of substitution.
glycoconjugates, phenolic glycolipid, Mycobacterium leprae, leprosy, PGL-I
Publication DOI: 10.1007/s11172-015-0991-6Journal NLM ID: 100912060Publisher: New York: Consultants Bureau
Correspondence: kononov@ioc.ac.ru
Institutions: N.D. Zelinsky Institute of Organic Chemistry Russian Academy of Sciences, 47 Leninsky prosp., Moscow, Russian Federation
Methods: 13C NMR, 1H NMR, TLC, chemical synthesis, chemical methods, MALDI-TOF MS, conjugation
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