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    National Tsing Hua University Institutional Repository > 生命科學院  > 生命科學系 > 期刊論文 >  Development of specific inhibitors for heparin-binding proteins based on the cobra cardiotoxin structure: an effective synthetic strategy for rationally modified heparin-like disaccharides and a trisaccharide


    Please use this identifier to cite or link to this item: http://nthur.lib.nthu.edu.tw/dspace/handle/987654321/48473


    Title: Development of specific inhibitors for heparin-binding proteins based on the cobra cardiotoxin structure: an effective synthetic strategy for rationally modified heparin-like disaccharides and a trisaccharide
    Authors: Weijun Ke;Dennis M. Whitfield;Jean-Robert Brisson;Gary Enright;Harold C. Jarrell;Wen-guey Wu
    教師: 吳文桂
    Date: 2005
    Publisher: Elsevier
    Relation: Carbohydrate Research,Elsevier,Volume 340,Issue 3,28 February 2005,Pages 355-372
    Keywords: 1,3-diaxial interactions
    heparin-like oligosaccharides
    L-iduronic acid building blocks
    glycosylations
    Abstract: Recently, a new heparin disaccharide-binding site on the convex side of cobra cardiotoxin (CTX) was identified by NMR spectroscopy and molecular modeling. To further characterize this site two heparin-like disaccharides were synthesized for binding studies with CTX, and a trisaccharide was synthesized for testing the sequence of the disaccharide binding to CTX. Thus six differentially protected monosaccharide building blocks (three L-iduronic acids and three D-glucosamines) were prepared. These include a L-iduronic acid elongation building block namely methyl 2-O-acetyl-4-O-levulinoyl-3-O-pivaloyl-alpha-L-idopyranosyluronate trichloroacetimidate for which a single-crystal X-ray structure was determined to have M-r = 576.79, a = 9.3098(11) Angstrom alpha = 90degrees, b = 10.3967(12) Angstrom beta = 90degrees, c = 28.026(3) Angstrom gamma = 90degrees, V = 2712.7(6) Angstrom(3), P2(1)2(1)2(1), Z = 4, mu = 0.71073 Angstrom, and R = 0.0378 for 7586 observed reflections. It shows that the molecular structure of the donor is in the C-1(4) conformation with significant 1,3-diaxial interactions between O-1 and O-3 as well as O-2 and O-4. The disaccharides and trisaccharide vary in the degree and position of O- and N-sulfation. The pivaloyl group was used as permanent protecting group of hydroxyl. The levulinoyl group was used as the temporary protecting group to protect the hydroxyl for elongation.
    URI: http://www.elsevier.com/
    http://nthur.lib.nthu.edu.tw/dspace/handle/987654321/48473
    Appears in Collections:[生命科學系] 期刊論文

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