synthesis of disaccharides containing 6-deoxy-a-l-talose as potential heparan sulfate mimetics合成含6-deoxy-a-l-talose作为潜在的二糖硫酸乙酰肝素模仿.pdfVIP

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synthesis of disaccharides containing 6-deoxy-a-l-talose as potential heparan sulfate mimetics合成含6-deoxy-a-l-talose作为潜在的二糖硫酸乙酰肝素模仿.pdf

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synthesis of disaccharides containing 6-deoxy-a-l-talose as potential heparan sulfate mimetics合成含6-deoxy-a-l-talose作为潜在的二糖硫酸乙酰肝素模仿

Molecules 2012, 17, 9790-9802; doi:10.3390/molecule OPEN ACCESS molecules ISSN 1420-3049 /journal/molecules Article Synthesis of Disaccharides Containing 6-Deoxy--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; E-Mail: v.ferro@.au; Tel.: +61-7-3346-9598; Fax: +61-7-3365-4299. Received: 28 June 2012; in revised form: 5 August 2012 / Accepted: 9 August 2012 / Published: 15 August 2012 Abstract: A 6-deoxy--L-talopyranoside acceptor was readily prepared from methyl -L-rhamnopyranoside and glycosylated with thiogalactoside donors using NIS/TfOH as the promoter to give good yields of the desired -linked disaccharide (69–90%). Glycosylation with a 2-azido-2-deoxy-D-glucosyl trichloroacetimidate donor was not completely stereoselective (: = 6:1), but the desired -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