Taxonomic group: fungi / Ascomycota
(Phylum: Ascomycota)
NCBI PubMed ID: 28531457Publication DOI: 10.1016/j.carres.2017.05.008Journal NLM ID: 0043535Publisher: Elsevier
Correspondence: Handley PN <paul.handley
zucero.com.au>; Carroll A <a.carroll
griffith.edu.au>; Ferro V <v.ferro
uq.edu.au>
Institutions: Progen Pharmaceuticals Ltd, Darra, Australia, Griffith Institute for Drug Discovery, Griffith University, Nathan, Australia
The oligosaccharide phosphate fraction (OPF) obtained from mild acid hydrolysis of P. holstii NRRL Y-2448 phosphomannan is the starting material for the preparation of the Phase III anticancer drug candidate PI-88. The OPF was for the first time successfully separated by preparative ion exchange chromatography and the major oligosaccharides isolated and characterized by NMR spectroscopy. The components were also acetylated and subjected to LC-MS analysis. These studies revealed that the OPF also contained all-α(1→3)-linked oligosaccharides in addition to the known α(1→3)/(1→2)-linked species, most likely formed by hydrolysis of the latter. Contrary to previous assumptions, the only phosphorylated disaccharide present is α(1→3)-linked. In addition, it was determined that a glycosylamine derivative previously isolated is, in fact, a manufacturing byproduct formed from exposure to aqueous ammonium bicarbonate during chromatographic purification. Based on these findings a new generic structure for PI-88 is proposed which more accurately reflects its composition.
Oligosaccharides, NMR spectroscopy, structure elucidation, PI-88
Structure type: oligomer
Location inside paper: oligosaccharide 10, fig. 1
Trivial name: mannobiose
Compound class: EPS, mannan
Contained glycoepitopes: IEDB_130701,IEDB_136104,IEDB_137485,IEDB_143632,IEDB_144983,IEDB_152206,IEDB_983930,SB_136,SB_196,SB_44,SB_67,SB_72
Methods: 13C NMR, 1H NMR, FAB-MS, ESI-MS, HPLC, acetylation, HPLC-MS, HMBC, COSY, HSQC
Comments, role: Imprint volume is 446-447
Related record ID(s): 43233, 43234, 43235, 43236, 43237, 43238, 43239, 43240, 43241, 43242, 43243, 43244, 43245, 43246, 43247, 43248, 43249
NCBI Taxonomy refs (TaxIDs): 36025Reference(s) to other database(s): GTC:G29313LW
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There is only one chemically distinct structure:
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(previously named: Pichia holstii NRRL Y-2448; later renamed to: Nakazawaea holstii NRRL Y-2448)