De novo synthesis of uronic acid building blocks for assembly of heparin oligosaccharides |
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Authors: | Adibekian Alexander Bindschädler Pascal Timmer Mattie S M Noti Christian Schützenmeister Nina Seeberger Peter H |
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Institution: | Laboratory for Organic Chemistry, Swiss Federal Institute of Technology ETH Zürich, Wolfgang-Pauli-Strasse 10, HCI F312, 8093 Zürich, Switzerland. |
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Abstract: | An efficient de novo synthesis of uronic acid building blocks is described. The synthetic strategy relies on the stereoselective elongation of thioacetal protected dialdehydes 12 a and 17. The dialdehydes are prepared from D-xylose, a cheap and commercially available source. A highly stereoselective MgBr(2)OEt(2)-mediated Mukaiyama aldol addition to C4-aldehyde 12 a is performed to obtain D-glucuronic acid building block 16, whereas L-iduronic acid building block 22 is prepared by MgBr(2)OEt(2)-mediated cyanation of C5-aldehyde 17. Synthesis of a heparin disaccharide demonstrates the utility of the de novo strategy for the assembly of glycosaminoglycan oligosaccharides. |
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Keywords: | carbohydrates de novo synthesis heparin oligosaccharides uronic acids |
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