Abstract
Recent advances in polymer‐supported synthesis of oligosaccharides, i. e., solid-phase synthesis, polymer‐supported synthesis, and tag-assisted solution synthesis, are overviewed. A variety of new methods on polymer‐supports, combined with accumulation of information on oligosaccharides synthesis in solution, has led to the assembly of complex oligosaccharide structures in the solid-phase, and even to a programmed automation system. A continuous flow synthesis of oligosaccharides using a microreactor, a newly appearing protocol for glycosylation analysis, high-throughput- and combinatorial synthesis, and even for production-scale synthesis, will also be described.
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Abbreviations
- Bn:
-
benzyl
- Bz:
-
benzoyl
- CAN:
-
ammonium cerium(IV) nitrate
- ClAc:
-
chloroacetyl
- DIPEA:
-
diisopropylethylamine
- DMF:
-
dimethylformamide
- DMM:
-
dimethylmaleoyl
- DMTSB:
-
dimethyl(methylthio)sulfonium tetrafluoroborate
- DMTST:
-
dimethyl(methylthio)sulfonium triflate
- DTBMP:
-
2,6-di-tert-butyl-4‑methylpyridine
- DTBP:
-
di-tert-butylpyridine
- EDTA:
-
ethylenediaminetetraacetic acid
- Fmoc:
-
9‑fluorenylmethoxycarbonyl
- HBTU:
-
2-(1H-benzotriazole-1-yl)-1,1,3,3‑tetramethyluronium hexafluorophosphate
- HEPES:
-
N-(2‑hydroxyethyl)-piperazine-N′-(2‑ethanesulfonic acid)
- HOBt:
-
1‑hydroxybenzotriazole
- Lev:
-
levulinoyl
- MALDI-TOF-MS:
-
matrix-assisted laser desorption ionization mass spectrometry
- MES:
-
2‑morpholinoethanesulfonic acid
- MPEG:
-
polyethylene glycol monomethyl ether
- MS:
-
molecular sieves
- NIPAm:
-
N-i-propylacrylamide
- NIS:
-
N‑iodosuccinimide
- PEG:
-
polyethylene glycol
- Pht:
-
phthalyl
- Piv:
-
pivaloyl
- PS-PEG:
-
polystyrene-polyethylene glycol
- PyBOP:
-
(1H-benzotriazole-1-yloxy) tripyrrolidinophosphonium hexafluorophosphate
- TBDMS:
-
tert-butyldimethylsilyl
- TCA:
-
trichloroacetyl
- TFA:
-
trifluoroacetic acid
- TMSOTf:
-
trimethylsilyl triflate
- Troc:
-
2,2,2‑trichloroethoxycarbonyl
- UDP:
-
uridine diphosphate
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Tanaka, K., Fukase, K. (2008). Polymer-Supported and Tag-Assisted Methods in Oligosaccharide Synthesis. In: Fraser-Reid, B.O., Tatsuta, K., Thiem, J. (eds) Glycoscience. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-540-30429-6_29
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DOI: https://doi.org/10.1007/978-3-540-30429-6_29
Publisher Name: Springer, Berlin, Heidelberg
Print ISBN: 978-3-540-36154-1
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