Synthesis of Disaccharides Containing 6-Deoxy-a-L-talose as Potential Heparan Sulfate Mimetics

doi:10.3390/molecules17089790

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Molecules 2012, 17(8), 9790-9802; doi:10.3390/molecules17089790

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Synthesis of Disaccharides Containing 6-Deoxy-a-L-talose as Potential Heparan Sulfate Mimetics

Jon K. Fairweather, Ligong Liu^†, Tomislav Karoli^† and Vito Ferro^‡,*

Drug Design Group, Progen Pharmaceuticals Ltd, Brisbane QLD 4076, Australia ^† Current address: Institute for Molecular Bioscience, The University of Queensland, Brisbane, QLD 4072, Australia. ^‡ Current address: School of Chemistry and Molecular Biosciences, The University of Queensland, Brisbane, QLD 4072, Australia.

* Author to whom correspondence should be addressed.

Received: 28 June 2012; in revised form: 5 August 2012 / Accepted: 9 August 2012 / Published: 15 August 2012

(This article belongs to the Special Issue Advances in Carbohydrate Chemistry)

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Abstract: A 6-deoxy-a-L-talopyranoside acceptor was readily prepared from methyl a-L-rhamnopyranoside and glycosylated with thiogalactoside donors using NIS/TfOH as the promoter to give good yields of the desired a-linked disaccharide (69–90%). Glycosylation with a 2-azido-2-deoxy-D-glucosyl trichloroacetimidate donor was not completely stereoselective (a:b = 6:1), but the desired a-linked disaccharide could be isolated in good overall yield (60%) following conversion into its corresponding tribenzoate derivative. The disaccharides were designed to mimic the heparan sulfate (HS) disaccharide GlcN(2S,6S)-IdoA(2S). However, the intermediates readily derived from these disaccharides were not stable to the sulfonation/deacylation conditions required for their conversion into the target HS mimetics.

Keywords: disaccharides; heparan sulfate mimetics; fibroblast growth factors

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Cite This Article

MDPI and ACS Style

Fairweather, J.K.; Liu, L.; Karoli, T.; Ferro, V. Synthesis of Disaccharides Containing 6-Deoxy-a-L-talose as Potential Heparan Sulfate Mimetics. Molecules 2012, 17, 9790-9802.

AMA Style

Fairweather JK, Liu L, Karoli T, Ferro V. Synthesis of Disaccharides Containing 6-Deoxy-a-L-talose as Potential Heparan Sulfate Mimetics. Molecules. 2012; 17(8):9790-9802.

Chicago/Turabian Style

Fairweather, Jon K.; Liu, Ligong; Karoli, Tomislav; Ferro, Vito. 2012. "Synthesis of Disaccharides Containing 6-Deoxy-a-L-talose as Potential Heparan Sulfate Mimetics." Molecules 17, no. 8: 9790-9802.

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