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Molecules 2016, 21(5), 614; doi:10.3390/molecules21050614

Efficient Synthesis of the Lewis A Tandem Repeat

1
Department of Applied Bioorganic Chemistry, Gifu University, 1-1 Yanagido, Gifu-shi, Gifu 501-1193, Japan
2
Institute for Integrated Cell-Material Sciences (WPI Program), Kyoto University, Yoshida-ushinomiya-cho, Sakyo-ku, Kyoto-shi, Kyoto 606-8302, Japan
3
Faculty of Pharmaceutical Sciences, Aomori University, 2-3-1 Kobata, Aomori-shi, Aomori 030-0943, Japan
*
Authors to whom correspondence should be addressed.
Academic Editors: Vito Ferro and Trinidad Velasco-Torrijos
Received: 11 April 2016 / Revised: 4 May 2016 / Accepted: 6 May 2016 / Published: 11 May 2016
(This article belongs to the Collection Advances in Carbohydrate Chemistry)
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Abstract

The convergent synthesis of the Lewis A (Lea) tandem repeat is described. The Lea tandem repeat is a carbohydrate ligand for a mannose binding protein that shows potent inhibitory activity against carcinoma growth. The Lea unit, {β-d-Gal-(1→3)-[α-l-Fuc-(1→4)]-β-d-GlcNAc}, was synthesized by stereoselective nitrile-assisted β-galactosylation with the phenyl 3-O-allyl-2,4,6-tri-O-benzyl-1-thio-β-galactoside, and ether-assisted α-fucosylation with fucosyl (N-phenyl)trifluoroacetimidate. This common Lea unit was easily converted to an acceptor and donor in high yields, and the stereoselective assembly of the hexasaccharide and dodecasaccharide as the Lea tandem repeat framework was achieved by 2-trichloroacetamido-assisted β-glycosylation and the (N-phenyl)trifluoroacetimidate method. View Full-Text
Keywords: Lewis A tandem repeat; convergent synthesis; sugar-binding protein Lewis A tandem repeat; convergent synthesis; sugar-binding protein
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Kobayashi, D.; Ueki, A.; Yamaji, T.; Nagao, K.; Imamura, A.; Ando, H.; Kiso, M.; Ishida, H. Efficient Synthesis of the Lewis A Tandem Repeat. Molecules 2016, 21, 614.

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