TY - CHAP
T1 - S
AU - Fukase, Koichi
AU - Tanaka, Katsunori
AU - Fujimoto, Yukari
AU - Shimoyama, Atsushi
AU - Manabe, Yoshiyuki
N1 - Publisher Copyright:
© 2016 John Wiley & Sons, Inc.
PY - 2015/1/1
Y1 - 2015/1/1
N2 - 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.
AB - 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.
KW - Asparagine
KW - Microflow synthesis
KW - Microfluidic systems
KW - N-glycosylation
KW - Oligosaccharide synthesis
KW - Stereoselective glycosylation
KW - Synthetic intermediates
KW - α-sialylation
KW - β-mannosylation
UR - http://www.scopus.com/inward/record.url?scp=85017447680&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=85017447680&partnerID=8YFLogxK
U2 - 10.1002/9781119006435.ch8
DO - 10.1002/9781119006435.ch8
M3 - Chapter
AN - SCOPUS:85017447680
SN - 9781118299845
SP - 205
EP - 219
BT - Glycochemical Synthesis
PB - Wiley Blackwell
ER -