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Exploring the native chemical ligation concept for highly stereospecific glycosylation reactions.

Kim Le Mai Hoang, Yaguang Bai, Xin Ge, Xue-Wei Liu

Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, 21 Nanyang Link, Singapore 637371.

The Journal of organic chemistry 2013 Jun 7


filter terms:
  • chemical concept (2)
  • glycoconjugates (1)
  • glycosides (1)
  • glycosylation (1)
  • ligation (2)
  • native (2)
    • Sizes of these terms reflect their relevance to your search.

    Various O-alkyl glycosides were obtained in a highly stereospecific manner with retention of configuration at the anomeric center. Our method has customized native chemical ligation concept for glycoconjugates synthesis, utilizing a meticulously controlled activating system. To explain the origin of stereoselective preference, an S(N)i mechanism was proposed and corroborated by computational calculations.

    Citation

    Kim Le Mai Hoang, Yaguang Bai, Xin Ge, Xue-Wei Liu. Exploring the native chemical ligation concept for highly stereospecific glycosylation reactions. The Journal of organic chemistry. 2013 Jun 7;78(11):5196-204


    PMID: 23638656

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