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Polymer-Supported and Tag-Assisted Methods in Oligosaccharide Synthesis

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Book cover Glycoscience

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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Author information

Authors and Affiliations

  1. Department of Chemistry, Graduate School of Science, Osaka University, Osaka, 560-0043, Japan

    Katsunori Tanaka & Koichi Fukase

Authors
  1. Katsunori Tanaka
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  2. Koichi Fukase
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Editor information

Editors and Affiliations

  1. Natural Products and Glycotechnology Research Institute Inc., North Caroline State University, 4118 Swarthmore Road, Durham, NC, 27707, USA

    Bertram O. Fraser-Reid Prof. Dr.

  2. University Graduate School of Science and Engineering, 3-4-1 Ohkubo, Shinjuku, Tokyo, Japan

    Kuniaki Tatsuta Prof. Dr.

  3. Faculty of ScienceDepartment of Chemistry, University of Hamburg, Martin-Luther-King-Platz 6, 20146, Hamburg, Germany

    Joachim Thiem Prof. Dr.

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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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