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Taxonomic group: fungi / Ascomycota (Phylum: Ascomycota)
Associated disease: infection due to Candida albicans [ICD11: XN31P]

NCBI PubMed ID: 35068914
Publication DOI: 10.1007/s11172-021-3334-9
Journal NLM ID: 7505544
Publisher: Moscow: Nauka
Correspondence: Nifantiev NE <nen

ioc.ac.ru>
Institutions: N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prospect, Moscow, Russian Federation, Department of Immunochemistry of Glycoconjugates, Institute of Chemistry, Slovak Academy of Sciences, Bratislava, Slovakia

The polysaccharide mannan is the main surface antigen of the cell wall of Candida fungi, playing an important role in the pathogenesis of diseases caused by these mycopathogens. Mannan has a complex, comb-like structure and includes a variety of structural units, with their combination varying depending on the Candida species and strain. Glucomannan, a polysaccharide from Candida utilis, contains terminal α-d-glucose residues attached to oligomannoside side chains. This paper describes the first synthesis of a pentasaccharide structurally related to C. utilis glucomannan fragment, which is an α-(1→2)-linked tetramannoside terminated at the non-reducing end by an α-d-glucopyranosyl residue. The pentasaccharide was obtained as a 3-aminopropyl glycoside, which made it possible to synthesize also its biotinylated derivative, suitable for various glycobiological studies. The most complicated step in the pentasaccharide synthesis was stereoselective 1,2-cis-glycosylation to attach the α-d-glucopyranosyl residue. This was accomplished using a glucosyl donor specially developed in our laboratory, the protecting groups of which provide the necessary α-stereoselectivity. The target biotinylated pentasaccharide thus obtained will be used in the future as a model antigen for the detection of immunodeterminant epitopes of Candida mannans.

synthesis, antigen, oligosaccharide, 1, 2-cis-Glycosylation, Glucomannan, Candida utilis

Structure type: polymer chemical repeating unit
Location inside paper: p. 2209, Fig. 1a, mannan
Trivial name: mannan
Compound class: cell wall polysaccharide
Contained glycoepitopes: IEDB_128161,IEDB_130701,IEDB_131173,IEDB_133966,IEDB_133967,IEDB_134618,IEDB_134620,IEDB_134621,IEDB_136104,IEDB_137485,IEDB_140116,IEDB_141111,IEDB_141793,IEDB_141795,IEDB_141828,IEDB_141829,IEDB_141830,IEDB_141831,IEDB_141832,IEDB_141833,IEDB_141834,IEDB_142357,IEDB_143632,IEDB_144983,IEDB_144994,IEDB_144995,IEDB_144996,IEDB_152206,IEDB_153220,IEDB_153756,IEDB_153762,IEDB_153763,IEDB_1539315,IEDB_164174,IEDB_164175,IEDB_164176,IEDB_164177,IEDB_164479,IEDB_164480,IEDB_173895,IEDB_174840,IEDB_2278480,IEDB_241100,IEDB_474450,IEDB_76920,IEDB_76933,IEDB_857732,IEDB_857735,IEDB_858578,IEDB_983930,SB_136,SB_191,SB_196,SB_197,SB_198,SB_44,SB_67,SB_72,SB_73

Methods: 13C NMR, 1H NMR, NMR-2D, TLC, ESI-MS, chemical synthesis, optical rotation measurement, biotinylation

Related record ID(s): 41146, 41147
NCBI Taxonomy refs (TaxIDs): 5476
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](OC[C@H]5O[C@H](OC[C@H]6O[C@H](OC[C@H]7O[C@H](OC[C@H]8O[C@H](*)[C@@H](O[C@H]9O[C@H](CO)[C@@H](O)[C@H](O)[C@@H]9O[C@H]9O[C@H](COP(=O)(O)O[C@H]%10O[C@H](CO)[C@@H](O)[C@H](O)[C@@H]%10O[C@@H]%10O[C@H](CO)[C@@H](O)[C@H](O)[C@@H]%10O[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]8O)[C@@H](O[C@H]8O[C@H](CO)[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]8O[C@H](CO)[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]7O)[C@@H](O[C@H]7O[C@H](CO)[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]7O[C@H](CO[C@H]8O[C@H](CO)[C@@H](O)[C@H](O)[C@@H]8O)[C@@H](O)[C@H](O[C@H]8O[C@H](CO)[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]7O)[C@@H](O)[C@@H]6O)[C@@H](O[C@H]6O[C@H](CO)[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]6O[C@H](CO[C@H]7O[C@H](CO)[C@@H](O)[C@H](O)[C@@H]7O)[C@@H](O)[C@H](O[C@H]7O[C@H](CO)[C@@H](O)[C@H](O)[C@@H]7O)[C@@H]6O)[C@@H](O)[C@@H]5O)[C@@H](O[C@H]5O[C@H](CO)[C@@H](O)[C@H](O)[C@@H]5O[C@H]5O[C@H](CO)[C@@H](O)[C@H](O[C@H]6O[C@H](CO)[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]6O[C@H](CO)[C@@H](O)[C@H](O)[C@@H]6O)[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]4O[C@H](CO)[C@@H](O)[C@H](O)[C@@H]4O[C@H]4O[C@H](CO)[C@@H](O)[C@H](O[C@H]5O[C@H](CO)[C@@H](O)[C@H](O)[C@@H]5O)[C@@H]4O)[C@@H](O)[C@@H]3O)[C@@H](O[C@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@@H]3O[C@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@@H]3O)[C@@H](O)[C@@H]2O)[C@@H](O)[C@@H](O)[C@@H]1O

SVG MW SMILES 3D mol Ionize

Warning = sub-repeat ending at bDManp: variable unit count (0-2) was assumed to be 0
Warning = sub-repeat ending at bDManp: variable unit count (0-4) was assumed to be 0
Warning = sub-repeat ending at aDManp: variable unit count (0-3) was assumed to be 0