Regioselective one-pot protection of carbohydrates

Cheng-Chung Wang, Jinq-Chyi Lee, Shun-Yuan Luo, Suvarn S. Kulkarni, Yu-Wen Huang, Chia-Chen Lee, Ken-Lien Chang and Shang-Cheng Hung ()
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Cheng-Chung Wang: National Tsing Hua University, Hsinchu 300, 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,
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

Nature, 2007, vol. 446, issue 7138, 896-899

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.

Date: 2007
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DOI: 10.1038/nature05730

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