Found 7 structures.
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1. Compound ID: 3804
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a-L-Rhap4Me-(1-4)-a-L-Fucp2Me-(1-3)-a-L-Rhap-(1-2)-a-L-6dTalp-(1-3)-D-aThr-(?--/N-acylpeptide LIP(1-2)xDPhe(1-2)xDaThr(1-2)xDAla?(1-2)Subst // Subst = alaninol = SMILES N{2}[C@@H](C){1}CO/ |
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Structure type: oligomer
Aglycon: N-acylpeptide LIP(1-2)xDPhe(1-2)xDaThr(1-2)xDAla?(1-2)Subst // Subst = alaninol = SMILES N{2}[C@@H](C){1}CO
Trivial name: oligosaccharide hapten
Compound class: glycopeptidolipid (GPL)
Contained glycoepitopes: IEDB_136045,IEDB_136098,IEDB_136099,IEDB_136105,IEDB_142489,IEDB_144562,IEDB_152214,IEDB_174333,IEDB_225177,IEDB_885823,SB_86
The structure is contained in the following publication(s):
- Article ID: 1450
Chatterjee D, Khoo KH "The surface glycopeptidolipids of mycobacteria: structures and biological properties" -
Cellular and Molecular Life Sciences 58(14) (2001) 2018-2042
One of the most important opportunistic pathogens associated with acquired immunodeficiency syndrome (AIDS) is the M. avium complex. M. avium infections are found in up to 70% of individuals in advanced stages of AIDS. It is apparent that M. avium can replicate in host macrophages and persist for long periods. This group of mycobacteria are distinguished by the presence of unique, highly antigenic, surface- located lipids known as the glycopeptidolipids (GPLs). The GPLs are the chemical basis of the 31 distinct serovars of the M. avium complex, and have also been identified in some other species. The M. avium lipids are immunosuppressive and can induce a variety of cytokines that affect general host responses. Despite extensive chemical characterization of the structures of these GPLs, much work is needed to elucidate the molecular mechanism involved in this complex glycosylation pathway and its genetic basis. The challenges for the future lie in explaining the roles of these copious products in the intracellular life and infectivity of mycobacteria. The intention of our review is to offer a concise account of the structures of the M. avium lipids, their putative roles in the host responses, bacterial physiology and pathogenesis, particularly in immunocompromised patients such as those infected with human immunodeficiency virus (HIV). Advances in chemical synthesis of the various haptenic oligosaccharides are also given to demonstrate how these have helped to define the immunogenic determinants. We believe that future research should involve the creation of conditional mutants defective in these lipids for both functional and biosynthesis studies which will complement biological assays using chemically defined or modified neoglycoconjugates
Mycobacteria, neoglycoproteins, glycopeptidolipid (GPL), Mycobacterium avium complex (MAC), haptenic oligosaccharides
NCBI PubMed ID: 11814054Publication DOI: 10.1007/PL00000834Journal NLM ID: 9705402Publisher: Basel: Springer
Correspondence: delphi@lamar.colostate.edu
Institutions: Department of Microbiology, Colorado State University, Fort Collins 80523, USA, Institute of Biological Chemistry, Academia Sinica, Taipei (Taiwan)
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2. Compound ID: 4467
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Subst1-(1-2)-Phe-(1-2)-+
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a-L-Rhap4Me-(1-4)-a-L-Fucp2Me-(1-3)-a-L-Rhap-(1-2)-b-L-6dTalp-(1-3)-Thr-(1-2)-Ala-(1-2)-Subst2-(1-1)-L-Rhap3Me4Me
Subst1 = 3-hydroxyheneicosanoic acid = SMILES CCCCCCCCCCCCCCCCCCC(O)C{1}C(O)=O;
Subst2 = alaninol = SMILES N{2}C(C){1}CO |
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Structure type: oligomer
Compound class: glycopeptidolipid
Contained glycoepitopes: IEDB_136045,IEDB_136098,IEDB_136099,IEDB_136105,IEDB_137476,IEDB_137477,IEDB_142489,IEDB_144562,IEDB_152214,IEDB_174333,IEDB_225177,IEDB_885823,SB_86
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
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3. Compound ID: 5787
Structure type: oligomer
Contained glycoepitopes: IEDB_136045,IEDB_136098,IEDB_136099,IEDB_136105,IEDB_142489,IEDB_144562,IEDB_152214,IEDB_174333,IEDB_225177,IEDB_885823,SB_86
The structure is contained in the following publication(s):
- Article ID: 2539
Rivoire B, Ranchoff BJ, Chatterjee D, Gaylord H, Tsang AY, Kolk AHJ, Aspinall GO, Brennan PJ "Generation of monoclonal antibodies to the specific sugar epitopes of Mycobacterium avium complex serovars" -
Infection and Immunity 57 (1989) 3147-3158
Monoclonal antibodies have been generated to the unique distal sugar epitopes on the oligosaccharide haptens of the glycopeptidolipid antigens of clinically prominent members of the Mycobacterium avium serocomplex. Thus, antibodies are described that recognize the distal O-acetyl-α-L-rhamnopyranosyl residue of the specific glycopeptidolipid of M. avium serovar 1, the 4-O-acetyl-2,3-di-O-methyl-α-L-fucopyranose of serovar 2, the 4-O-methyl-α-L-rhamnopyranosyl-(1→4)-2-O-methyl-α-L-fucopyranosyl unit of serovar 4, the 4,6-(1'-carboxyethylidene)-3-O-methyl-β-D-glucopyranosyl unit of serovar 8 [and the 4,6-(1'-carboxyethylidene)-β-D-glucopyranosyl residue of serovar 21], and the 4-O-acetyl-2,3-di-O-methyl-α-L-fucopyranosyl-(1→4)-β-D-glucuronopyranosyl unit of serovar 9. Epitope definition was arrived at through use of the pure, chemically defined glycopeptidolipid antigens and neoglycoproteins containing the chemically synthesized distal sugars of some select serovars. These monoclonal antibodies combined with the already published information on the structure of the antigen determinants and the tools used to arrive at these structures provide powerful means for fundamental studies on the role of these antigens in immunopathogenesis and for the precise mapping of the epidemiology of opportunistic infections caused by M. avium.
NCBI PubMed ID: 2476400Journal NLM ID: 0246127Publisher: American Society for Microbiology
Institutions: Department of Microbiology, Colorado State University, Fort Collins 80523
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4. Compound ID: 5794
Structure type: oligomer
Trivial name: GPL
Compound class: glycopeptidolipid
Contained glycoepitopes: IEDB_136045,IEDB_136098,IEDB_136099,IEDB_136105,IEDB_142489,IEDB_144562,IEDB_152214,IEDB_174333,IEDB_225177,IEDB_885823,SB_86
The structure is contained in the following publication(s):
- Article ID: 2543
Tassell SK, Pourshafie M, Wright EL, Richmond MG, Barrow WW "Modified lymphocyte response to mitogens induced by the lipopeptide fragment derived from mycobacterium avium serovar-specific glycopeptidolipids" -
Infection and Immunity 60 (1992) 706-711
The beta-elimination procedure was used to obtain two major fragments of Mycobacterium avium glycopeptidolipid antigens. The lipopeptide fragment, not the oligosaccharide, diminished the mitogen-induced blastogenic response of spleen cells at concentrations lower than those which affected viability. Electron microscopy revealed an internalization of lipopeptide and disruption of intracellular organization.
NCBI PubMed ID: 1730507Journal NLM ID: 0246127Publisher: American Society for Microbiology
Institutions: Department of Microbiology and Immunology, Texas College of Osteopathic Medicine, Fort Worth 76107-2690
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5. Compound ID: 5924
Structure type: oligomer
Trivial name: hapten
Contained glycoepitopes: IEDB_136045,IEDB_136098,IEDB_136099,IEDB_136105,IEDB_142489,IEDB_144562,IEDB_152214,IEDB_174333,IEDB_225177,IEDB_885823,SB_86
The structure is contained in the following publication(s):
- Article ID: 2635
McNeil M, Tsang AY, Brennan PJ "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" -
Journal of Biological Chemistry 262(6) (1987) 2630-2635
A large number of patients with acquired immune deficiency syndrome develop disseminated infections due to member serotypes of the Mycobacterium avium complex. Seroagglutination on 181 such isolates followed by enzyme-linked immunosorbent assay and thin layer chromatography of the type-specific glycopeptidolipid (GPL) antigens demonstrated that the majority of serotypes were M. avium serotype 4. The specific GPL of serotype 4 was isolated in both the native, acetylated, and the deacetylated forms and its oligosaccharide hapten released as the oligosaccharide alditol by reductive β-elimination. A comprehensive structural analytical approach developed for more complex carbohydrates was applied to the oligosaccharide alditol in order to reveal glycosyl and glycosyl-linkage composition, sequence arrangements, ring forms, and enantiomeric and anomeric configurations. The structure of the triglycosyl alditol was established as, 4-O-Me-L-Rhap-(α1→4)-2-O-Me-L-Fucp-(α1→3)-L-Rhap-(α1→2)-6-deoxytalitol, in which the nonreducing-end disaccharide unit is unique to serotype 4. The native GPL antigen is diacetylated, presumably at other than the terminal disaccharide, since the antigenicity of both the acetylated and deacetylated antigens are comparable. The structure of the epitope of the type-specific antigen of serotype 4 will serve as the basis for synthetic antigen probes and the target for the monoclonal antibodies required to trace the origins in the environment of the infectious agent and study the epidemiology of human infections.
NCBI PubMed ID: 2434488Journal NLM ID: 2985121RPublisher: Baltimore, MD: American Society for Biochemistry and Molecular Biology
Institutions: Department of Microbiology, Colorado State University, Fort Collins, Colorado 80523
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6. Compound ID: 6056
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LIP-(1-2)-D-Phe-(1-2)-+
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a-L-Rhap4Me-(1-4)-a-L-Fucp2Me-(1-3)-a-L-Rhap-(1-2)-b-L-6dTalp-(1-3)-D-aThr-(1-2)-D-Ala-(1-2)-Subst2-(1-1)-L-Rhap3Me4Me
Subst2 = alaninol = SMILES N{2}C(C){1}CO |
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Structure type: oligomer
Trivial name: GPL
Compound class: glycopeptidolipid
Contained glycoepitopes: IEDB_136045,IEDB_136098,IEDB_136099,IEDB_136105,IEDB_137476,IEDB_137477,IEDB_142489,IEDB_144562,IEDB_152214,IEDB_174333,IEDB_225177,IEDB_885823,SB_86
The structure is contained in the following publication(s):
- Article ID: 2702
Woodbury JL, Barrow WW "Radiolabelling of Mycobacterium avium oligosaccharide determinant and use in macrophage studies" -
Journal of General Microbiology 135 (1989) 1875-1884
Internal radiolabelling procedures were used to radiolabel the oligosaccharide determinant of the glycopeptidolipids (GPL) from serovars 4 and 20 of the Mycobacterium avium complex. Mycobacteria were cultured in the presence of [6-3H]fucose, [2-3H]mannose or [methyl-3H]methionine, after which radiolabelled native lipid was extracted and distribution of radioactivity in native and deacetylated lipid was determined by thin-layer chromatographic methods. Incorporation of radiolabel was confirmed by examining acid hydrolysates of purified GPL for 3H-labelled sugars on cellulose thin-layer plates. Least incorporation of radiolabel into GPL was observed with [6-3H]fucose, whereas better incorporation was obtained with [2-3H]mannose and [methyl-3H]methionine. Use of [methyl-3H]methionine resulted in the radiolabelling of the methylated sugars in both the oligosaccharide determinant and the 3,4-di-O-methylrhamnose located at the terminus of the peptide core. Use of [2-3H]mannose resulted in the incorporation of radioactivity into the oligosaccharide determinant as 2-O-methylfucose, found in the GPL of both serovars 4 and 20. GPL radiolabelled with [2-3H]mannose were subsequently examined in macrophage cultures and found to be relatively inert to degradation by those phagocytic cells. These results substantiate earlier findings with the GPL of serovar 20 and indicate that these mycobacterial components may play a role in pathogenesis.
NCBI PubMed ID: 2482334Publication DOI: 10.1099/00221287-135-7-1875Journal NLM ID: 0375371Institutions: Department of Microbiology and Immunology, Texas College of Osteopathic Medicine, Fort Worth 76107
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7. Compound ID: 13327
Structure type: oligomer
Contained glycoepitopes: IEDB_136045,IEDB_136098,IEDB_136099,IEDB_136105,IEDB_142489,IEDB_144562,IEDB_152214,IEDB_174333,IEDB_225177,IEDB_885823,SB_86
The structure is contained in the following publication(s):
- Article ID: 5293
Miyamoto Y, Mukai T, Naka T, Fujiwara N, Maeda Y, Kai M, Mizuno S, Yano I, Makino M "Novel rhamnosyltransferase involved in biosynthesis of serovar 4-specific glycopeptidolipid from Mycobacterium avium complex" -
Journal of Bacteriology 192(21) (2010) 5700-5708
Glycopeptidolipids (GPLs) are one of the major glycolipid components present on the surface of Mycobacterium avium complex (MAC) that belong to opportunistic pathogens distributed in the natural environment. The serovars of MAC, up to around 30 types, are defined by the variable oligosaccharide portions of the GPLs. Epidemiological studies show that serovar 4 is the most prevalent type, and the prognosis of pulmonary disease caused by serovar 4 is significantly worse than that caused by other serovars. However, little is known about the biosynthesis of serovar 4-specific GPL, particularly the formation of the oligosaccharide portion that determines the properties of serovar 4. To investigate the biosynthesis of serovar 4-specific GPL, we focused on one segment that included functionally unknown genes in the GPL biosynthetic gene cluster of a serovar 4 strain. In this segment, a putative hemolytic protein gene, hlpA, and its downstream gene were found to be responsible for the formation of the 4-O-methyl-rhamnose residue, which is unique to serovar 4-specific GPL. Moreover, functional characterization of the hlpA gene revealed that it encodes a rhamnosyltransferase that transfers a rhamnose residue via 1→4 linkage to a fucose residue of serovar 2-specific GPL, which is a key pathway leading to the synthesis of oligosaccharide of serovar 4-specific GPL. These findings may provide clues to understanding the biological role of serovar 4-specific GPL in MAC pathogenicity and may also provide new insights into glycosyltransferase, which generates structural and functional diversity of GPLs.
Mycobacterium avium, rhamnosyltransferase, GPL biosynthesis
NCBI PubMed ID: 20817766Publication DOI: 10.1128/JB.00554-10Journal NLM ID: 2985120RPublisher: American Society for Microbiology
Correspondence: Miyamoto Y
Institutions: Department of Mycobacteriology, Leprosy Research Center, National Institute of Infectious Diseases, Tokyo, Japan, Department of Bacteriology, Osaka City University, Graduate School of Medicine, Osaka, Japan, MBR Co., Ltd., Osaka, Japan, Faculty of Human Development, Soai University, Osaka, Japan, Japan BCG Laboratory, Tokyo, Japan
Methods: DNA sequencing, GC-MS, DNA techniques, TLC, MALDI-TOF MS, extraction, cell growth
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