S

Koichi Fukase, Katsunori Tanaka, Yukari Fujimoto, Atsushi Shimoyama, Yoshiyuki Manabe

Research output: Chapter in Book/Report/Conference proceedingChapter

Abstract

This chapter investigates the applications of the advantageous features of the microfluidic systems to oligosaccharide synthesis. It explains successful examples that employed this technique including α-sialylation, β-mannosylation, N-glycosylation on asparagine, α-selective glycosylation of 3-deoxy-D-manno-2-octulosonic acid (KDO), β-selective glucosaminylation and reductive opening of the benzylidene acetal groups in sugars. The improved procedure under the microfluidic conditions enabled the preparation of key synthetic intermediates for oligosaccharides in multigram scales, eventually leading to the synthesis of the asparagine-linked oligosaccharide (N-glycan) and Helicobacter pylori lipopolysaccharide (LPS) partial structures. The microfluidic reactions can offer a practical route for stereoselective glycosylation. Continuous microflow synthesis is an innovative technology for chemical processes from small-scale synthesis to large-scale production. This technology enables fast and efficient mixing, rapid heating and cooling, strict temperature control, precise residence time control, and effective mass transfer. Microfluidic synthesis enables high mixing efficiency as well as precise temperature control and can achieve the ideal reaction kinetics.

Original languageEnglish
Title of host publicationGlycochemical Synthesis
Subtitle of host publicationStrategies and Applications
PublisherWiley Blackwell
Pages205-219
Number of pages15
ISBN (Electronic)9781119006435
ISBN (Print)9781118299845
DOIs
Publication statusPublished - 2015 Jan 1

Keywords

  • Asparagine
  • Microflow synthesis
  • Microfluidic systems
  • N-glycosylation
  • Oligosaccharide synthesis
  • Stereoselective glycosylation
  • Synthetic intermediates
  • α-sialylation
  • β-mannosylation

ASJC Scopus subject areas

  • Chemistry(all)

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    Fukase, K., Tanaka, K., Fujimoto, Y., Shimoyama, A., & Manabe, Y. (2015). S. In Glycochemical Synthesis: Strategies and Applications (pp. 205-219). Wiley Blackwell. https://doi.org/10.1002/9781119006435.ch8