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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, 344(17), pp. 2394-2398.

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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-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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ID Code: 27851
Item Type: Journal Article
Keywords: heparan sulfate mimetics, disaccharides, fibroblast growth factors
DOI: 10.1016/j.carres.2009.09.012
ISSN: 0008-6215
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
Copyright Statement: This is the author’s version of a work that was accepted for publication in Carbohydrate Research. Changes resulting from the publishing process, such as peer review, editing, corrections, structural formatting, and other quality control mechanisms may not be reflected in this document. Changes may have been made to this work since it was submitted for publication. A definitive version was subsequently published in Carbohydrate Research, [VOL 344, ISSUE 17, (2009)] DOI: 10.1016/j.carres.2009.09.012
Deposited On: 12 Oct 2009 12:24
Last Modified: 30 Oct 2013 10:58

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