Further structural definition of a new family of glycopeptidolipids from Mycobacterium xenopi.

The highly antigenic surface glycolipids of serovars of the Mycobacterium avium complex are glycopeptidolipids of the general structure [formula: see text] However, it has recently been shown [Rivière, M., & Puzo, G. (1991) J. Biol. Chem. 266, 9057-9063; Rivière, M., & Puzo, G. (1992) Biochemistry 31, 3575-3580] that the characteristic glycopeptidolipid of a strain of Mycobacterium xenopi is of the structure [formula: see text] [monosaccharide, 3-O-CH3-6-deoxy-alpha-L-talopyranose; tetrasaccharide, 2,3,4-tri-O-CH3-alpha-L-rhamnopyranose(1-->3)2-O-lauryl-alpha-L- rhamnopyranose(1-->3)2,4-di-O-acetyl/lauryl-6-deoxy-alpha-L-glucopyranos e]. The type of analyses previously applied to the glycopeptidolipids of M. avium combined with fast atom bombardment mass spectrometry allowed the recognition of other variants of this structure in other strains of M. xenopi: [formula: see text] in which the monosaccharide is 2-O-acetyl-3-O-CH3-6-deoxy-alpha-L-talopyranose or 3-O-CH3-6-deoxy-alpha-L-talopyranose, and the disaccharide is 4-O-octanoyl(or decanoyl)-alpha-L- rhamnopyranose(1-->3)2-O-lauryl-alpha-L-rhamnopyranose or alpha-L-rhamnopyranose(1-->3)2-O-lauryl-alpha-L-rhamnopyranose. Recognition of serine-containing glycopeptidolipids substituted in one case with a tetrasaccharide and in another case with a disaccharide unit implies that M. xenopi, an important opportunistic pathogen, exists as a serocomplex in nature.

[1]  M. Rivière,et al.  Use of 1H NMR ROESY for structural determination of O-glycosylated amino acids from a serine-containing glycopeptidolipid antigen. , 1992, Biochemistry.

[2]  P. Brennan,et al.  Clinical and epidemiological importance of typing of Mycobacterium avium complex isolates , 1992, Journal of clinical microbiology.

[3]  M. Daffé,et al.  Glycopeptidolipids from Mycobacterium fortuitum: a variant in the structure of C-mycoside. , 1991, Biochemistry.

[4]  D. Minnikin,et al.  Structural elucidation and antigenicity of a novel phenolic glycolipid antigen from Mycobacterium haemophilum. , 1991, Biochemistry.

[5]  M. Rivière,et al.  A new type of serine-containing glycopeptidolipid from Mycobacterium xenopi. , 1991, The Journal of biological chemistry.

[6]  P. Brennan,et al.  Lipoarabinomannan, a possible virulence factor involved in persistence of Mycobacterium tuberculosis within macrophages , 1991, Infection and immunity.

[7]  S. Noordeen A look at world leprosy. , 1991, Leprosy review.

[8]  P. Brennan,et al.  Peptidoglycan-associated polypeptides of Mycobacterium tuberculosis , 1990, Journal of bacteriology.

[9]  A. Kolk,et al.  Generation of monoclonal antibodies to the specific sugar epitopes of Mycobacterium avium complex serovars , 1989, Infection and immunity.

[10]  J. Belisle,et al.  Chemical basis of rough and smooth variation in mycobacteria , 1989, Journal of bacteriology.

[11]  P. Brennan,et al.  Plasma desorption mass spectrometric analysis of mycobacterial glycolipids. , 1989, Analytical chemistry.

[12]  H. Rubin Tort, contract, and the patient-physician relationship. , 1988, Annals of internal medicine.

[13]  M. Luquin,et al.  Mycobacterium xenopi infections in the acquired immunodeficiency syndrome. , 1988, Annals of internal medicine.

[14]  P. Brennan,et al.  Trehalose-containing lipooligosaccharide antigens of Mycobacterium sp.: presence of a mono-O-methyltri-O-acyltrehalose "core". , 1988, Biochemistry.

[15]  P. Brennan,et al.  Location of acyl groups of trehalose-containing lipooligosaccharides of mycobacteria , 1987, Journal of bacteriology.

[16]  P. Brennan,et al.  The presence of novel glucuronic acid-containing, type-specific glycolipid antigens within Mycobacterium spp. Revision of earlier structures. , 1987, The Journal of biological chemistry.

[17]  P. Brennan,et al.  Structure and antigenicity of the specific oligosaccharide hapten from the glycopeptidolipid antigen of Mycobacterium avium serotype 4, the dominant Mycobacterium isolated from patients with acquired immune deficiency syndrome. , 1987, The Journal of biological chemistry.

[18]  P. Brennan,et al.  Trehalose-containing lipooligosaccharides from mycobacteria: structures of the oligosaccharide segments and recognition of a unique N-acylkanosamine-containing epitope. , 1985, Biochemistry.

[19]  G. Puzo,et al.  Structural elucidation by field desorption and electron-impact mass spectrometry of the C-mycosides isolated from Mycobacterium smegmatis. , 1983, Biochimica et biophysica acta.

[20]  P. Prehm Methylation of carbohydrates by methyl trifluoromethanesulfonate in trimethyl phosphate , 1980 .

[21]  P. Brennan,et al.  Structural studies on the type-specific antigens and lipids of the mycobacterium avium. Mycobacterium intracellulare. Mycobacterium scrofulaceum serocomplex. Mycobacterium intracellulare serotype 9. , 1979, The Journal of biological chemistry.

[22]  G. Chambat,et al.  Chemical and 13C N.M.R. studies on two arabinans from the inner bark of young stems of Rosa glauca , 1977 .

[23]  S. Mackenzie,et al.  Rapid formation of amino acid isobutyl esters for gas chromatography. , 1975, Journal of chromatography.

[24]  E. L. Armstrong,et al.  Site of inhibitory action of isoniazid in the synthesis of mycolic acids in Mycobacterium tuberculosis. , 1975, Journal of lipid research.

[25]  P. Jenkins,et al.  Thin-layer chromatography of mycobacterial lipids as an aid to classification: The Scotochromogenic Mycobacteria, including Mycobacterium scrofulaceum The scotochromonegic Mycobacteria, including mycobacterium scrofulaceum, M.xenopi, M. . xenopi, M. aquae, M. gordonae, M. flavescens , 1972 .

[26]  J. Asselineau,et al.  Structure d'un glycoside de peptidolipide isolé d'une mycobactérie , 1968 .

[27]  E. Lederer,et al.  Structure du mycoside Cm, peptido-glycolipide de Mycobacterium marianum , 1962 .

[28]  M. Ikawa,et al.  The occurence of D-allo-isoleucine and D-leucine in mycosides and peptido-lipids of bacterial origin , 1962 .

[29]  J. Folch,et al.  A simple method for the isolation and purification of total lipides from animal tissues. , 1957, The Journal of biological chemistry.

[30]  G. Puzo The carbohydrate- and lipid-containing cell wall of mycobacteria, phenolic glycolipids: structure and immunological properties. , 1990, Critical reviews in microbiology.

[31]  A. Dell Preparation and desorption mass spectrometry of permethyl and peracetyl derivatives of oligosaccharides. , 1990, Methods in enzymology.

[32]  P. Brennan,et al.  Mycobacterial glycolipids: isolation, structures, antigenicity, and synthesis of neoantigens. , 1989, Methods in enzymology.

[33]  Horsburgh Cr,et al.  The epidemiology of disseminated nontuberculous mycobacterial infection in the acquired immunodeficiency syndrome (AIDS). , 1989 .

[34]  P. Brennan,et al.  Leprosy and the leprosy bacillus: recent developments in characterization of antigens and immunology of the disease. , 1987, Annual review of microbiology.

[35]  A. Dell,et al.  F.A.B.-mass spectrometry of carbohydrates. , 1987, Advances in carbohydrate chemistry and biochemistry.

[36]  P. Albersheim,et al.  Isolation and characterization of plant cell walls and cell wall components , 1986 .

[37]  E. Lederer,et al.  N-methylation de peptides par la methode de hakomori. Structure du mycoside Cbl. , 1968 .