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 language | English |
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Title of host publication | Glycochemical Synthesis |
Subtitle of host publication | Strategies and Applications |
Publisher | Wiley Blackwell |
Pages | 205-219 |
Number of pages | 15 |
ISBN (Electronic) | 9781119006435 |
ISBN (Print) | 9781118299845 |
DOIs | |
Publication status | Published - 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)