The synthesis of phosphorylated disaccharide components of the extracellular phosphomannan of Pichia (Hansenula) holstii NRRL Y-2448

Fairweather, Jon K., Karoli, Tomislav and Ferro, Vito (2004) The synthesis of phosphorylated disaccharide components of the extracellular phosphomannan of Pichia (Hansenula) holstii NRRL Y-2448. Bioorganic & Medicinal Chemistry, 12 23: 6063-6075. doi:10.1016/j.bmc.2004.09.005


Author Fairweather, Jon K.
Karoli, Tomislav
Ferro, Vito
Title The synthesis of phosphorylated disaccharide components of the extracellular phosphomannan of Pichia (Hansenula) holstii NRRL Y-2448
Formatted title
The synthesis of phosphorylated disaccharide components of the extracellular phosphomannan of Pichia (Hansenula) holstii NRRL Y-2448
Journal name Bioorganic & Medicinal Chemistry   Check publisher's open access policy
ISSN 0968-0896
1464-3391
Publication date 2004-12-01
Sub-type Article (original research)
DOI 10.1016/j.bmc.2004.09.005
Volume 12
Issue 23
Start page 6063
End page 6075
Total pages 13
Place of publication Oxford, U.K.
Publisher Pergamon
Language eng
Subject 0304 Medicinal and Biomolecular Chemistry
1115 Pharmacology and Pharmaceutical Sciences
Formatted abstract
Methods for the stereoselective synthesis of α-(1→2)- and α-(1→3)-linked 6II-O-phosphomannobiosides were developed. Two strategies were successfully employed: a D-mannosyl acceptor was coupled with a phosphorylated D-mannosyl trichloroacetimidate donor, or alternatively with a differentially 6-O-protected D-mannosyl trichloroacetimidate donor which, after glycosylation, was selectively deprotected and phosphorylated. Two target phosphomannobiosides intended for use in SAR studies of the antiangiogenic drug candidate PI-88, 2-O-(6-O-phospho-α-D-mannopyranosyl)-D-mannopyranose and methyl 3-O-(6-O-phospho-α-D-mannopyranosyl)-α-D-mannopyranoside, were synthesized. The former is a minor component of the side-chain repeating unit of the extracellular phosphomannan of Pichia (Hansenula) holstii NRRL Y-2448, whilst the latter represents a nonreducing end fragment of the phosphomannan.
© 2004 Elsevier Ltd. All rights reserved.
Keyword Phosphomannobiosides
Synthesis
Pichia
PI-88
Q-Index Code C1

Document type: Journal Article
Sub-type: Article (original research)
Collection: Excellence in Research Australia (ERA) - Collection
 
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Created: Fri, 26 Mar 2010, 19:23:23 EST by Jon Swabey on behalf of Institute for Molecular Bioscience