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Found 2 structures. Displayed structures from 1 to 2
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1. Compound ID: 12880

a-D-Manp-(1-2)-+ | a-D-Manp-(1-2)-+ | | | a-D-Manp-(1-2)-+ | | | | | a-D-Manp-(1-2)-+ | | | | | | | a-D-Manp-(1-2)-+ | | | | | | | | | a-D-Manp-(1-2)-+ | | | | | | | | | | | a-D-Manp-(1-2)-+ | | | | | | | | | | | | | a-D-Manp-(1-6)-+ | | | | | | | | | | | | | | | a-D-Manp-(1-2)-a-D-Manp-(1-6)-a-D-Manp-(1-6)-a-D-Manp-(1-6)-a-D-Manp-(1-6)-a-D-Manp-(1-6)-a-D-Manp-(1-6)-+ | | | | | b-D-Araf-(1-2)-a-D-Araf-(1-3)-+ | | | | | | | b-D-Araf-(1-2)-{{{-a-D-Araf-(1-5)-}}}/n=5/-a-D-Araf-(1-5)-a-D-Araf-(1-5)-{{{-a-D-Araf-(1-5)-}}}/n=2/-a-D-Araf-(1-3)-+ | | | | | | | a-D-Manp-(1-2)-a-D-Manp-(1-2)-b-D-Araf-(1-2)-a-D-Araf-(1-5)-a-D-Araf-(1-5)-+ | | | | | | | | | b-D-Araf-(1-2)-{{{-a-D-Araf-(1-5)-}}}/n=6/-a-D-Araf-(1-3)-a-D-Araf-(1-5)-a-D-Araf-(1-5)-a-D-Araf-(1-5)-a-D-Araf-(1-5)-a-D-Araf-(1-5)-{{{-a-D-Araf-(1-5)-}}}/n=3/-a-D-Araf-(1-3)-+ | | | | | | | b-D-Araf-(1-2)-a-D-Araf-(1-3)-+ | | | | | | | | | a-D-Manp-(1-2)-a-D-Manp-(1-2)-b-D-Araf-(1-2)-a-D-Araf-(1-5)-a-D-Araf-(1-5)-{{{-a-D-Araf-(1-5)-}}}/n=2/-a-D-Araf-(1-5)-a-D-Araf-(1-3)-+ | | | | | | | | | a-D-Manp-(1-2)-b-D-Araf-(1-2)-a-D-Araf-(1-5)-+ | | | | | LIP-(1-?)-a-D-Manp-(1-?)-+ LIP-(1-1)-+ | | | | | | | | a-D-Xylf5S5Me-(1-4)-a-D-Manp-(1-2)-a-D-Manp-(1-2)-b-D-Araf-(1-2)-a-D-Araf-(1-3)-a-D-Araf-(1-5)-{{{-a-D-Araf-(1-5)-}}}/n=2/-a-D-Araf-(1-5)-a-D-Araf-(1-5)-a-D-Araf-(1-5)-{{{-a-D-Araf-(1-5)-}}}/n=2/-a-D-Araf-(1-5)-a-D-Araf-(1-5)-a-D-Araf-(1-5)-{{{-a-D-Araf-(1-5)-}}}/n=11/-a-D-Araf-(1-5)-D-Araf-(1-?)-a-D-Manp-(1-6)-a-D-Manp-(1-6)-a-D-Manp-(1-6)-a-D-Manp-(1-6)-a-D-Manp-(1-6)-a-D-Manp-(1-?)-myoIno-(1--P--3)--Gro | | Suc-(1-2)-+ LIP-(1-2)-+ Xyl5S = 5-thio-xylose

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Compound 12880

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Structure type: structural motif or average structure
Trivial name: lipoarabinomannan (LAM)
Compound class: cell wall polysaccharide
Contained glycoepitopes: IEDB_130701,IEDB_1309625,IEDB_1309626,IEDB_136104,IEDB_140116,IEDB_141793,IEDB_141828,IEDB_141829,IEDB_141831,IEDB_143632,IEDB_144983,IEDB_144993,IEDB_152206,IEDB_153220,IEDB_153762,IEDB_153763,IEDB_76933,IEDB_857718,IEDB_857732,IEDB_857735,IEDB_857736,IEDB_983930,SB_136,SB_191,SB_196,SB_198,SB_44,SB_67,SB_72

The structure is contained in the following publication(s):

Article ID: 5123
Angala SK, Palčeková Z, Belardinelli JM, Jackson M "Covalent modifications of polysaccharides in mycobacteria" - Nature Chemical Biology 14(3) (2018) 193-198

Mycobacteria produce carbohydrates of exceptional structures that are covalently modified by unique substituents, whose functional characterization could expand our understanding of how mycobacteria adapt to their environment.
polysaccharides, modification, Mycobacteria, covalent, arabinogalactan (AG), lipoarabinomannan (LAM), lipomannan (LM)
NCBI PubMed ID: 29443974
Publication DOI: 10.1038/nchembio.2571
Journal NLM ID: 101231976
Publisher: New York, NY: Nature Publishing Group
Correspondence: Mary.Jackson@ColoState.EDU
Institutions: Mycobacteria Research Laboratories, Department of Microbiology, Immunology and Pathology, Colorado State University, Fort Collins, Colorado, USA

Mycobacterium tuberculosis, Mycobacterium bovis BCG, Mycobacterium bovis, Mycobacterium leprae, Mycobacterium avium, Mycobacterium smegmatis
CSDB ID 13024 (all data & tools)

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2. Compound ID: 16593

{{{-a-D-Manp-(1-2)-}}}/n=6-7/-a-D-Manp-(1-2)-+ | b-D-Araf-(1-2)-a-D-Araf-(1-3)-+ | | | a-D-Manp-(1-2)-a-D-Manp-(1-2)-b-D-Araf-(1-2)-a-D-Araf-(1-5)-a-D-Araf-(1-5)-{{{-a-D-Araf-(1-5)-}}}a-D-Araf-(1-3)-+ | | | D-Manp-(1-?)-b-D-Araf-(1-2)-a-D-Araf-(1-5)-+ | | | | | Suc-(1-3)-+ | | | | | | | a-D-Xylf5S5Me-(1-4)-a-D-Manp-(1-2)-a-D-Manp-(1-5)-b-D-Araf-(1-2)-a-D-Araf-(1-3)-a-D-Araf-(1-5)-{{{-a-D-Araf-(1-5)-}}}a-D-Araf-(1-5)-a-D-Araf-(1-5)-{{{-a-D-Araf-(1-5)-}}}a-D-Araf-(1-5)-+ | | | | Suc-(1-2)-+ | | | | b-D-Araf-(1-2)-a-D-Araf-(1-3)-+ | | | | | b-D-Araf-(1-2)-{{{-a-D-Araf-(1-5)-}}}/n=5/-a-D-Araf-(1-5)-a-D-Araf-(1-5)-{{{-a-D-Araf-(1-5)-}}}a-D-Araf-(1-3)-+ | | | | | Suc-(1-3)-+ | | | | | | | Suc-(1-3)-+ a-D-Manp-(1-2)-a-D-Manp-(1-2)-a-D-Araf-(1-2)-b-D-Araf-(1-5)-a-D-Araf-(1-5)-+ | | a-D-Manp-(1-2)-+ | a-D-Manp-(1-2)-+ a-D-Manp-(1-2)-+ | | | | | | | | b-D-Araf-(1-2)-a-D-Araf-(1-5)-a-D-Araf-(1-5)-a-D-Araf-(1-5)-{{{-D-Araf-(1-?)-}}}a-D-Araf-(1-3)-a-D-Araf-(1-5)-{{{-a-D-Araf-(1-5)-}}}a-D-Araf-(1-5)-a-D-Araf-(1-5)-{{{-a-D-Araf-(1-5)-}}}a-D-Araf-(1-3)-a-D-Araf-(1-5)-{{{-a-D-Araf-(1-5)-}}}/n=13/-a-D-Araf-(1-6)-a-D-Manp-(1-6)-{{{-a-D-Manp-(1-6)-}}}/n=2/-a-D-Manp-(1-6)-{{{-a-D-Manp-(1-6)-}}}a-D-Manp-(1-6)-{{{-a-D-Manp-(1-6)-}}}/n=2/-a-D-Manp-(1-6)-a-D-Manp-(1-6)-a-D-Manp-(1--/phosphatidyl-myo-inositol anchor/ | Suc-(1-2)-+ Xyl5S = 5-thio-xylose

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Compound 16593

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Structure type: structural motif or average structure
Aglycon: phosphatidyl-myo-inositol anchor
Trivial name: lipoarabinomannan (LAM)
Compound class: cell wall polysaccharide
Contained glycoepitopes: IEDB_130701,IEDB_1309625,IEDB_1309626,IEDB_136104,IEDB_137485,IEDB_140116,IEDB_141793,IEDB_141795,IEDB_141828,IEDB_141829,IEDB_141830,IEDB_141831,IEDB_141834,IEDB_143632,IEDB_144983,IEDB_152206,IEDB_153220,IEDB_153762,IEDB_153763,IEDB_164480,IEDB_76933,IEDB_857718,IEDB_857732,IEDB_857735,IEDB_857736,IEDB_983930,SB_136,SB_191,SB_196,SB_198,SB_44,SB_67,SB_72

The structure is contained in the following publication(s):

Article ID: 6437
Palčeková Z, Obregón-Henao A, De K, Walz A, Lam H, Philp J, Angala SR, Patterson J, Pearce C, Zuberogoitia S, Avanzi C, Nigou J, McNeil M, Muñoz Gutiérrez JF, Gilleron M, Wheat WH, Gonzalez-Juarrero M, Jackson M "Role of succinyl substituents in the mannose-capping of lipoarabinomannan and control of inflammation in Mycobacterium tuberculosis infection" - PLoS Pathogens 19(9) (2023) e1011636

The covalent modification of bacterial (lipo)polysaccharides with discrete substituents may impact their biosynthesis, export and/or biological activity. Whether mycobacteria use a similar strategy to control the biogenesis of its cell envelope polysaccharides and modulate their interaction with the host during infection is unknown despite the report of a number of tailoring substituents modifying the structure of these glycans. Here, we show that discrete succinyl substituents strategically positioned on Mycobacterium tuberculosis (Mtb) lipoarabinomannan govern the mannose-capping of this lipoglycan and, thus, much of the biological activity of the entire molecule. We further show that the absence of succinyl substituents on the two main cell envelope glycans of Mtb, arabinogalactan and lipoarabinomannan, leads to a significant increase of pro-inflammatory cytokines and chemokines in infected murine and human macrophages. Collectively, our results validate polysaccharide succinylation as a critical mechanism by which Mtb controls inflammation.
lipoarabinomannan, Mycobacterium tuberculosis, tuberculosis
NCBI PubMed ID: 37669276
Publication DOI: 10.1371/journal.ppat.1011636
Journal NLM ID: 101238921
Publisher: San Francisco, CA: Public Library of Science
Correspondence: M. Jackson
Institutions: Mycobacteria Research Laboratories, Department of Microbiology, Immunology and Pathology, Colorado State University, Fort Collins, Colorado, United States of America, Institut de Pharmacologie et de Biologie Structurale, IPBS, Université de Toulouse, CNRS, UPS, Toulouse, France, Department of Microbiology, Immunology and Pathology, Colorado State University, Fort Collins, Colorado, United States of America
Methods: GC-MS, SDS-PAGE, composition analysis, genetic methods, biochemical methods, enzyme assay, statistical analysis, LC-MS, flow cytometry analysis, determination of NO production, macrophage activity assay, genome sequencing, succinylation, UPLC

Mycobacterium tuberculosis
CSDB ID 22287 (all data & tools)

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