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Regioselective one-pot protection of carbohydrates

Author

Listed:
  • Cheng-Chung Wang

    (National Tsing Hua University, Hsinchu 300, Taiwan
    Chemical Biology and Molecular Biophysics Program, Taiwan International Graduate Program, Academia Sinica, Taipei 115, Taiwan)

  • Jinq-Chyi Lee

    (National Tsing Hua University, Hsinchu 300, Taiwan)

  • Shun-Yuan Luo

    (National Tsing Hua University, Hsinchu 300, Taiwan)

  • Suvarn S. Kulkarni

    (Genomics Research Center,
    Institute of Chemistry,)

  • Yu-Wen Huang

    (National Tsing Hua University, Hsinchu 300, Taiwan)

  • Chia-Chen Lee

    (National Tsing Hua University, Hsinchu 300, Taiwan)

  • Ken-Lien Chang

    (National Tsing Hua University, Hsinchu 300, Taiwan)

  • Shang-Cheng Hung

    (National Tsing Hua University, Hsinchu 300, Taiwan
    Genomics Research Center,
    Institute of Chemistry,
    Chemical Biology and Molecular Biophysics Program, Taiwan International Graduate Program, Academia Sinica, Taipei 115, Taiwan)

Abstract

Carbohydrate synthesis The structural complexity that makes carbohydrates important in so many biological processes renders their chemical synthesis difficult. Though it is possible to synthesize pure oligosaccharides in the laboratory, the regioselective protection of hydroxyl groups and the stereoselective assembly of glycosidic bonds present a number of challenges for synthetic chemists. A new protocol that makes oligosaccharide synthesis both faster and less labour intensive is therefore most welcome. The first step involves the synthesis of hundreds of building blocks, starting from d-glucose, in a 'one-pot' reaction that selectively protects all but one of the monosaccharide's hydroxyl groups. Iterative coupling then incorporates these building blocks into complex oligosaccharides. The utility of this approach was demonstrated by rapidly synthesizing a small library of oligosaccharides based on the influenza virus-binding trisaccharide.

Suggested Citation

  • Cheng-Chung Wang & Jinq-Chyi Lee & Shun-Yuan Luo & Suvarn S. Kulkarni & Yu-Wen Huang & Chia-Chen Lee & Ken-Lien Chang & Shang-Cheng Hung, 2007. "Regioselective one-pot protection of carbohydrates," Nature, Nature, vol. 446(7138), pages 896-899, April.
    • Handle: RePEc:nat:nature:v:446:y:2007:i:7138:d:10.1038_nature05730
    DOI: 10.1038/nature05730
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