Synthesis of a heparan sulfate mimetic disaccharide with a conformationally locked residue from a common intermediate

Fairweather, J.K., Karoli, T., Liu, L., Bytheway, I. and Ferro, V. (2009) Synthesis of a heparan sulfate mimetic disaccharide with a conformationally locked residue from a common intermediate. Carbohydrate Research, 344 17: 2394-2398. doi:10.1016/j.carres.2009.09.012


Author Fairweather, J.K.
Karoli, T.
Liu, L.
Bytheway, I.
Ferro, V.
Title Synthesis of a heparan sulfate mimetic disaccharide with a conformationally locked residue from a common intermediate
Journal name Carbohydrate Research   Check publisher's open access policy
ISSN 0008-6215
Publication date 2009-11
Sub-type Article (original research)
DOI 10.1016/j.carres.2009.09.012
Volume 344
Issue 17
Start page 2394
End page 2398
Total pages 5
Place of publication United Kingdom
Publisher Elsevier
Language eng
Subject 0305 Organic Chemistry
0601 Biochemistry and Cell Biology
Abstract A simple mimetic of a heparan sulfate disaccharide sequence that binds to the growth factors FGF-1 and FGF-2 was synthesized by coupling a 2-azido-2-deoxy-d-glucopyranosyl trichloroacetimidate donor with a 1,6-anhydro-2-azido-2-deoxy-β-d-glucopyranose acceptor. Both the donor and acceptor were obtained from a common intermediate readily obtained from d-glucal. Molecular docking calculations showed that the predicted locations of the disaccharide sulfo groups in the binding site of FGF-1 and FGF-2 are similar to the positions observed for co-crystallized heparin-derived oligosaccharides obtained from published crystal structures.
Keyword Heparan sulfate mimetics
Disaccharides
Fibroblast growth factors
Q-Index Code C1
Q-Index Status Provisional Code

Document type: Journal Article
Sub-type: Article (original research)
Collections: ERA 2012 Admin Only
School of Chemistry and Molecular Biosciences
 
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Created: Mon, 27 Sep 2010, 09:36:15 EST by Laura McTaggart on behalf of Faculty of Science