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Taxonomic group: bacteria / Actinobacteria (Phylum: Actinobacteria)

NCBI PubMed ID: 26261090
Publication DOI: 10.1093/glycob/cwv061
Journal NLM ID: 9104124
Publisher: IRL Press at Oxford University Press
Correspondence: jerome.nigou

ipbs.fr
Institutions: CNRS, Institut de Pharmacologie et de Biologie Structurale (IPBS), UMR 5089 CNRS/Université Paul Sabatier, Toulouse, France, Université de Toulouse, Université Paul Sabatier, IPBS, Toulouse, France, Mycobacteria Research Laboratories, Department of Microbiology, Immunology and Pathology, Colorado State University, Fort Collins, USA

Mycobacterium tuberculosis lipoarabinomannan (LAM) and biosynthetically related lipoglycans and glycans play an important role in host-pathogen interactions. Therefore, the elucidation of the complete biosynthetic pathways of these important molecules is expected to afford novel therapeutic targets. The characterization of biosynthetic enzymes and transporters involved in the formation and localization of these complex macromolecules in the bacterial cell envelope largely relies on genetic manipulation of mycobacteria and subsequent analyses of lipoglycan structural alterations. However, lipoglycans are present in relatively low amounts. Their purification to homogeneity remains tedious and time-consuming. To overcome these issues and to reduce the biomass and time required for lipoglycan purification, we report here the development of a methodology to efficiently purify lipoglycans by sodium deoxycholate-polyacrylamide gel electrophoresis. This faster purification method can be applied on a small amount of mycobacterial cells biomass (10-50 mg), resulting in tens of micrograms of purified lipoglycans. This amount of purified products was found to be sufficient to undertake structural analyses of lipoglycans and glycans carbohydrate domains by a combination of highly sensitive analytical procedures, involving cryoprobe NMR analysis of intact macromolecules and chemical degradations monitored by gas chromatography and capillary electrophoresis. This glycomic approach was successfully applied to the purification and structural characterization of a newly identified polysaccharide, structurally related to LAM, in the model fast-growing species Mycobacterium smegmatis

polysaccharide, Mycobacterium, glycomic

Structure type: oligomer
Location inside paper: p. 33, mannan domain
Compound class: arabinomannan
Contained glycoepitopes: IEDB_130701,IEDB_136104,IEDB_140116,IEDB_141793,IEDB_141828,IEDB_141829,IEDB_141831,IEDB_143632,IEDB_144983,IEDB_152206,IEDB_153220,IEDB_153762,IEDB_153763,IEDB_76933,IEDB_857732,IEDB_857735,IEDB_983930,SB_136,SB_191,SB_196,SB_198,SB_44,SB_67,SB_72

Methods: deacetylation, 13C NMR, 1H NMR, NMR-2D, methylation, GC-MS, SDS-PAGE, acid hydrolysis, DOC-PAGE, GC, MALDI-TOF MS, GPC, enzymatic digestion, extraction, periodate oxidation, acetylation, acetolysis, determination of absolute configuration, reduction, column chromatography, dialysis, CE-LIF, fluorescence labeling, precipitation, derivatization, capillary electrophoresis, labeling

Related record ID(s): 49303, 49304
NCBI Taxonomy refs (TaxIDs): 246196
Show glycosyltransferases

There is only one chemically distinct structure:

OC[C@H]1O[C@H](OC[C@H]2O[C@H](OC[C@H]3O[C@H](OC[C@H]4O[C@H](O[C@@H]5[C@@H](OC[C@H]6O[C@H](OC[C@H]7O[C@H](OC[C@H]8O[C@H](OC[C@H]9O[C@H](O)[C@@H](O)[C@@H](O)[C@@H]9O)[C@@H](O)[C@@H](O)[C@@H]8O)[C@@H](O)[C@@H](O)[C@@H]7O)[C@@H](O)[C@@H](O)[C@@H]6O)O[C@H](CO[C@H]6O[C@H](CO[C@H]7O[C@H](CO[C@H]8O[C@H](CO[C@H]9O[C@H](CO[C@H]%10O[C@H](CO)[C@@H](O)[C@H](O)[C@@H]%10O)[C@@H](O)[C@H](O)[C@@H]9O[C@H]9O[C@H](CO)[C@@H](O)[C@H](O)[C@@H]9O)[C@@H](O)[C@H](O)[C@@H]8O[C@H]8O[C@H](CO)[C@@H](O)[C@H](O)[C@@H]8O)[C@@H](O)[C@H](O)[C@@H]7O[C@H]7O[C@H](CO)[C@@H](O)[C@H](O)[C@@H]7O)[C@@H](O)[C@H](O)[C@@H]6O[C@H]6O[C@H](CO)[C@@H](O)[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

Warning = sub-repeat ending at aDManp: unknown unit count was assumed to be 3
Warning = sub-repeat ending at aDManp: unknown unit count was assumed to be 3

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

]

NCBI PubMed ID: 25742868
Publication DOI: 10.1016/j.carres.2015.01.003
Journal NLM ID: 0043535
Publisher: Elsevier
Correspondence: Mandal PK <pintuchem06

gmail.com>
Institutions: Academy of Scientific and Innovative Research, New Delhi, India, Medicinal and Process Chemistry Division, CSIR-Central Drug Research Institute, Lucknow, India

The attachment of biotin to a molecule provides a powerful tool in biology. Here, we report an efficient synthesis and biotinylation of mannosylated and 5-deoxy-5-methylthio-xylofuranosylated Lipoarabinomannan from Mycobacterium tuberculosis. Preparation of the oligosaccharides involved the sequential addition of thioglycoside donors with arabinofuranosyl-containing acceptors. Methylthio group was introduced near the end of the synthesis

glycosylation, lipoarabinomannan (LAM), 5-deoxy-5-methylthio-xylofuranose (MTX), biotin, tuberculosis (TB)

Structure type: oligomer
Location inside paper: Fig. 1
Compound class: arabinomannan
Contained glycoepitopes: IEDB_130701,IEDB_144983,IEDB_152206,IEDB_983930,SB_44,SB_67,SB_72

Methods: 13C NMR, 1H NMR, IR, TLC, ESI-MS, chemical synthesis, optical rotation measurement, elemental analysis

NCBI Taxonomy refs (TaxIDs): 1773
Show glycosyltransferases

There is only one chemically distinct structure:

CSC[C@H]1O[C@H](O[C@@H]2[C@@H](CO)O[C@H](O[C@@H]3[C@@H](CO)O[C@H](OC[C@H]4O[C@@H](OC[C@H]5O[C@H](O[C@@H]6[C@@H](O[C@H]7[C@H](O)[C@@H](OC[C@H]8O[C@H](O)[C@@H](O)[C@@H]8O)O[C@@H]7CO[C@H]7O[C@H](CO)[C@@H](O)[C@@H]7O[C@H]7O[C@H](CO[C@@H]8O[C@H](CO[C@H]9O[C@H](CO)[C@@H](O[C@H]%10O[C@H](CO)[C@@H](O)[C@H](O)[C@@H]%10O)[C@H](O)[C@@H]9O)[C@@H](O)[C@@H]8O)[C@@H](O)[C@@H]7O)O[C@H](CO)[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