Synthesis of a heparan sulfate mimetic disaccharide with a conformationally locked residue from a common intermediate
Fairweather, Jon, Karoli, Tomislav, Liu, Ligong, Bytheway, Ian, & Ferro, Vito (2009) Synthesis of a heparan sulfate mimetic disaccharide with a conformationally locked residue from a common intermediate. Carbohydrate Research. (In Press)
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-glucosyl trichloroacetimidate donor with a 1,6-anhydro-2-azido-2-deoxy--D-glucose 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.
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|Item Type:||Journal Article|
|Keywords:||heparan sulfate mimetics, disaccharides, fibroblast growth factors|
|Subjects:||Australian and New Zealand Standard Research Classification > CHEMICAL SCIENCE (030000) > MEDICINAL AND BIOMOLECULAR CHEMISTRY (030400) > Biomolecular Modelling and Design (030402)|
|Divisions:||Past > QUT Faculties & Divisions > Faculty of Science and Technology|
Past > Schools > School of Physical & Chemical Sciences
|Copyright Owner:||Copyright 2009 Elsevier|
|Deposited On:||12 Oct 2009 12:24|
|Last Modified:||01 Mar 2012 00:08|
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