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Taxonomic group: protista / Euglenozoa (Phylum: Euglenozoa)
Host organism: Homo sapiens
Organ / tissue: cell surface, Life stage: promastigote
Associated disease: infection due to Leishmania donovani [ICD11: 1F54.0

, ICD11: XN1M5

]

NCBI PubMed ID: 22660966
Publication DOI: 10.1007/s10719-012-9400-7
Journal NLM ID: 8603310
Publisher: Kluwer Academic Publishers
Correspondence: s.hotha

iiserpune.ac.in
Institutions: Department of Chemistry, Indian Insititute of Science Education & Research, Pune, 411 008, India

Tetrasaccharide cap present in lipophosphoglycan of the Leishmania donovani responsible for visceral Leishmaniaisis is synthesized as a fully protected propargyl glycoside. AuBr(3) mediated selective glycosylation of propargyl 1,2-orthoester in the presence of propargyl glycoside is employed as a key step to obtain propargyl containing oligomers. Further, propargyl tetrasaccharide is connected with a long chain hydrocarbon containing azidothiol functionality situated at two terminal ends via 'click' reaction.

tetrasaccharide, leishmania, lipophosphoglycan, glycosidation, orthoester, gold catalysis

Structure type: oligomer
Location inside paper: p. 222, Fig. 1, LPG
Aglycon: lipid
Compound class: LPG
Contained glycoepitopes: IEDB_130701,IEDB_134623,IEDB_134624,IEDB_136044,IEDB_136095,IEDB_136100,IEDB_136104,IEDB_136906,IEDB_137472,IEDB_140116,IEDB_141794,IEDB_141807,IEDB_141830,IEDB_142349,IEDB_142350,IEDB_142488,IEDB_143632,IEDB_144983,IEDB_144993,IEDB_144996,IEDB_144998,IEDB_145002,IEDB_146664,IEDB_151528,IEDB_151531,IEDB_152206,IEDB_164174,IEDB_189518,IEDB_190606,IEDB_433717,IEDB_474450,IEDB_983930,IEDB_983931,SB_136,SB_163,SB_165,SB_166,SB_187,SB_192,SB_195,SB_196,SB_197,SB_44,SB_67,SB_7,SB_72,SB_88

Methods: 13C NMR, 1H NMR, IR, chemical synthesis, MALDI-TOF MS, optical rotation measurement, gold catalysis

NCBI Taxonomy refs (TaxIDs): 5661
Show glycosyltransferases

There is only one chemically distinct structure:

N[C@H]1[C@@H](O[C@@H]2[C@@H](OP(=O)(O)O)[C@@H](O)[C@@H](O)[C@H](O)[C@H]2O)O[C@H](CO)[C@@H](O[C@H]2O[C@H](CO)[C@@H](O)[C@H](O[C@H]3O[C@H](COP(=O)(O)O[C@H]4O[C@H](CO)[C@@H](O)[C@H](O)[C@H]4O)[C@@H](O)[C@H](O[C@@H]4O[C@@H]([C@H](O)CO)[C@H](O[C@H]5O[C@H](CO[C@H]6O[C@H](COP(=O)(O)O[C@H]7O[C@H](CO)[C@@H](O[C@@H]8O[C@H](COP(=O)(O)O[C@H]9O[C@H](CO)[C@@H](O[C@@H]%10O[C@H](COP(=O)(O)O[C@H]%11O[C@H](CO)[C@@H](O[C@@H]%12O[C@H](COP(=O)(O)O[C@H]%13O[C@H](CO)[C@@H](O[C@@H]%14O[C@H](CO)[C@H](O)[C@H](O)[C@H]%14O)[C@H](O)[C@@H]%13O[C@H]%13O[C@H](CO)[C@@H](O)[C@H](O)[C@@H]%13O[C@H]%13O[C@H](CO)[C@@H](O)[C@H](O)[C@@H]%13O)[C@H](O)[C@H](O)[C@H]%12O)[C@H](O)[C@@H]%11O)[C@H](O)[C@H](O)[C@H]%10O)[C@H](O)[C@@H]9O)[C@H](O)[C@H](O)[C@H]8O)[C@H](O)[C@@H]7O)[C@H](O)[C@H](O)[C@H]6O)[C@H](O)[C@H](O)[C@H]5O)[C@H]4O)[C@@H]3O)[C@@H]2O)[C@@H]1O

SVG MW SMILES 3D mol Ionize

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