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Taxonomic group: bacteria / Actinobacteria (Phylum: Actinobacteria)
Associated disease: infection due to Mycobacterium tuberculosis [ICD11: XN1N2

]

The structure was elucidated in this paper
NCBI PubMed ID: 29716995
Publication DOI: 10.1074/jbc.RA118.002582
Journal NLM ID: 2985121R
Publisher: Baltimore, MD: American Society for Biochemistry and Molecular Biology
Correspondence: Delphi.chatterjee

colostate.edu
Institutions: Mycobacteria Research Laboratories, Department of Microbiology, Immunology and Pathology, Department of Internal Medicine, Saint Louis University, St. Louis, Missouri 63104, Central Instrument Facility, Department of Chemistry, Colorado State University, Fort Collins, Colorado 80523

Mycobacteria synthesize intracellular, 6-O-methylglucose-containing lipopolysaccharides (mGLPs) proposed to modulate bacterial fatty acid metabolism. Recently, it has been shown that Mycobacterium tuberculosis mGLP specifically induces a specific subset of protective γ9δ2 T cells. Mild base treatment, which removes all the base-labile groups, reduces the specific activity of mGLP required for induction of these T cells, suggesting that acylation of the saccharide moieties is required for γ9δ2 T-cell activation. On the basis of this premise, we used analytical LC/MS and NMR methods to identify and locate the acyl functions on the mGLP saccharides. We found that mGLP is heterogeneous with respect to acyl functions and contains acetyl, isobutyryl, succinyl, and octanoyl groups and that all acylations in mGLP, except for succinyl and octanoyl residues, reside on the glucosyl residues immediately following the terminal 3-O-methylglucose. Our analyses also indicated that the octanoyl residue resides at position 2 of an internal glucose toward the reducing end. LC/MS analysis of the residual product obtained by digesting the mGLP with pancreatic ?-amylase revealed that the product is an oligosaccharide terminated by α-(1→4)-linked 6-O-methyl-d-glucosyl residues. This oligosaccharide retained none of the acyl groups, except for the octanoyl group, and was unable to induce protective γ9δ2 T cells. This observation confirmed that mGLP induces γ9δ2 T cells and indicated that the acylated glucosyl residues at the nonreducing terminus of mGLP are required for this activity.

Lipopolysaccharide, structural analysis, vaccine, Mycobacterium tuberculosis, lipoglycan, tuberculosis, carbohydrate chemistry, carbohydrate function, analytical chemistry, γδ T cells

Structure type: oligomer
Location inside paper: p.9713, fig.6, E1 product
Compound class: LPS
Contained glycoepitopes: IEDB_140629,IEDB_142488,IEDB_144998,IEDB_146664,IEDB_420417,IEDB_420418,IEDB_420421,IEDB_857742,IEDB_983931,SB_192

Methods: gel filtration, 1H NMR, NMR-2D, TLC, deacylation, composition analysis, enzymatic digestion, LC-MS, SEC, LC-ESI-MS, γ9δ2 T cell-stimulatory activity
Biological activity: E1 product was showed inability for T-cell expansion at concentration 0.01 or 0.1 µg/ml
Enzymes that release or process the structure: porcine α(1-4) amylase
Comments, role: E1 major product after digestion of native mGLP with α-amylase

Related record ID(s): 12545, 12892
NCBI Taxonomy refs (TaxIDs): 83332
Show glycosyltransferases

There is only one chemically distinct structure:

CCCCCCCC(=O)O[C@H]1[C@@H](OC[C@H]2O[C@H](OC(CO)C(=O)O)[C@H](O)[C@@H](O)[C@@H]2O)O[C@H](CO)[C@@H](O[C@H]2O[C@H](COC)[C@@H](O[C@H]3O[C@H](COC)[C@@H](O[C@H]4O[C@H](COC)[C@@H](O[C@H]5O[C@H](COC)[C@@H](O[C@H]6O[C@H](COC)[C@@H](O[C@H]7O[C@H](COC)[C@@H](O[C@H]8O[C@H](COC)[C@@H](O[C@H]9O[C@H](COC)[C@@H](O[C@H]%10O[C@H](COC)[C@@H](O[C@H]%11O[C@H](COC)[C@@H](O[C@H]%12O[C@H](COC)[C@@H](O[C@H]%13O[C@H](COC)[C@@H](O)[C@H](O)[C@H]%13O)[C@H](O)[C@H]%12O)[C@H](O)[C@H]%11O)[C@H](O)[C@H]%10O)[C@H](O)[C@H]9O)[C@H](O)[C@H]8O)[C@H](O)[C@H]7O)[C@H](O)[C@H]6O)[C@H](O)[C@H]5O)[C@H](O)[C@H]4O)[C@H](O[C@@H]4O[C@H](CO)[C@@H](O)[C@H](O)[C@H]4O)[C@H]3O)[C@H](O)[C@H]2O)[C@@H]1O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O

SVG MW SMILES 3D mol Ionize

Taxonomic group: bacteria / Actinobacteria (Phylum: Actinobacteria)
Associated disease: infection due to Mycobacterium tuberculosis [ICD11: XN1N2

Lipopolysaccharide, structural analysis, vaccine, Mycobacterium tuberculosis, lipoglycan, tuberculosis, carbohydrate chemistry, carbohydrate function, analytical chemistry, γδ T cells

Structure type: oligomer
Location inside paper: p.9712, fig.5, octaglucoside
Trivial name: mGLP
Contained glycoepitopes: IEDB_140629,IEDB_142488,IEDB_144998,IEDB_146664,IEDB_420417,IEDB_420418,IEDB_420421,IEDB_857742,IEDB_983931,SB_192

Methods: gel filtration, 1H NMR, NMR-2D, TLC, deacylation, composition analysis, enzymatic digestion, LC-MS, SEC, LC-ESI-MS, γ9δ2 T cell-stimulatory activity
Comments, role: octaglucoside of the nonreducing end of native mGLP (tandem Ms analysis of mGLP)

Related record ID(s): 12544, 12892
NCBI Taxonomy refs (TaxIDs): 83332
Show glycosyltransferases

There is only one chemically distinct structure:

COC[C@H]1O[C@H](O)[C@H](O)[C@@H](O)[C@@H]1O[C@H]1O[C@H](COC)[C@@H](O[C@H]2O[C@H](COC)[C@@H](O[C@H]3O[C@H](COC)[C@@H](O[C@H]4O[C@H](COC(C)=O)[C@@H](O[C@H]5O[C@H](CO)[C@@H](O[C@H]6O[C@H](COC(C)=O)[C@@H](O[C@H]7O[C@H](COC(=O)C(C)C)[C@@H](O)[C@H](OC)[C@H]7O)[C@H](O)[C@H]6O)[C@H](O)[C@H]5O)[C@H](O)[C@H]4O)[C@H](O)[C@H]3O)[C@H](O)[C@H]2O)[C@H](O)[C@H]1O

SVG MW SMILES 3D mol Ionize

Taxonomic group: bacteria / Actinobacteria (Phylum: Actinobacteria)
Associated disease: infection due to Mycobacterium tuberculosis [ICD11: XN1N2

]

NCBI PubMed ID: 29716995
Publication DOI: 10.1074/jbc.RA118.002582
Journal NLM ID: 2985121R
Publisher: Baltimore, MD: American Society for Biochemistry and Molecular Biology
Correspondence: Delphi.chatterjee

Lipopolysaccharide, structural analysis, vaccine, Mycobacterium tuberculosis, lipoglycan, tuberculosis, carbohydrate chemistry, carbohydrate function, analytical chemistry, γδ T cells

Structure type: oligomer
Location inside paper: p.9713, fig.6, native mGLP
Trivial name: mGLP
Compound class: LPS
Contained glycoepitopes: IEDB_140629,IEDB_142488,IEDB_144998,IEDB_146664,IEDB_420417,IEDB_420418,IEDB_420421,IEDB_857742,IEDB_983931,SB_192

Methods: gel filtration, 1H NMR, NMR-2D, TLC, deacylation, composition analysis, enzymatic digestion, LC-MS, SEC, LC-ESI-MS, γ9δ2 T cell-stimulatory activity

Related record ID(s): 12544, 12545
NCBI Taxonomy refs (TaxIDs): 83332
Show glycosyltransferases

There is only one chemically distinct structure:

CCCCCCCC(=O)O[C@H]1[C@@H](OC[C@H]2O[C@H](OC(CO)C(=O)O)[C@H](O)[C@@H](O)[C@@H]2O)O[C@H](COC(=O)CCC(=O)O)[C@@H](O[C@H]2O[C@H](COC)[C@@H](O[C@H]3O[C@H](COC)[C@@H](O[C@H]4O[C@H](COC)[C@@H](O[C@H]5O[C@H](COC)[C@@H](O[C@H]6O[C@H](COC)[C@@H](O[C@H]7O[C@H](COC)[C@@H](O[C@H]8O[C@H](COC)[C@@H](O[C@H]9O[C@H](COC)[C@@H](O[C@H]%10O[C@H](COC)[C@@H](O[C@H]%11O[C@H](COC)[C@@H](O[C@H]%12O[C@H](COC)[C@@H](O[C@H]%13O[C@H](COC)[C@@H](O[C@H]%14O[C@H](COC(C)=O)[C@@H](O[C@H]%15O[C@H](COC(C)=O)[C@@H](O[C@H]%16O[C@H](COC(C)=O)[C@@H](O[C@H]%17O[C@H](COC(=O)C(C)C)[C@@H](O)[C@H](OC)[C@H]%17O)[C@H](O)[C@H]%16O)[C@H](O)[C@H]%15O)[C@H](O)[C@H]%14O)[C@H](O)[C@H]%13O)[C@H](O)[C@H]%12O)[C@H](O)[C@H]%11O)[C@H](O)[C@H]%10O)[C@H](O)[C@H]9O)[C@H](O)[C@H]8O)[C@H](O)[C@H]7O)[C@H](O)[C@H]6O)[C@H](O)[C@H]5O)[C@H](O)[C@H]4O)[C@H](O[C@@H]4O[C@H](CO)[C@@H](O)[C@H](O)[C@H]4O)[C@H]3O)[C@H](O)[C@H]2O)[C@@H]1O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O

SVG MW SMILES 3D mol Ionize