4.6 Article

Synthesis of a Sialic Acid Containing Complex-Type N-Glycan on a Solid Support

Journal

CHEMISTRY-AN ASIAN JOURNAL
Volume 4, Issue 4, Pages 574-580

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/asia.200800411

Keywords

carbohydrates; glycoproteins; glycosylation; microfluidics; solid-phase synthesis

Funding

  1. Japan Society for the Promotion of Science [19681024, 19651095]
  2. Japan Science and Technology Agency (JST)
  3. New Energy and Industrial Technology Development Organization (NEDO) [07A01014a]
  4. Yamada Science Foundation
  5. Ministry of Education, Culture, Sports, Science and Technology (MEXT) of Japan

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A new solid-phase synthesis of N-linked glycans featuring 1.) highly stereoselective beta-mannosylation and microfluidic alpha-sialylation and 2) efficient glycosylation of the N-phenyltrifluoroacetimidate units on JandaJel resin is reported. Reagent concentration effects by a fluorous solvent are effectively applied,. and the use of these methods results in the first synthesis of a sialic acid containing complex-type N-glycan on a solid support.

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