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Combinatorial Methods in Oligosaccharide Synthesis

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Glycoscience

Abstract

This chapter will focus on recent achievements in the combinatorial approach to glycobiology. Significant advances in polymer‐supported synthesis as well as chemoenzymic methods have led to the assembly of complex oligosaccharides in a combinatorial fashion even on desired positions of target peptides or proteins. The successful application of oligosaccharide libraries and carbohydrate mimetics to glycobiology such as elucidation of the immunobiological function of glycoconjugates or the discovery of carbohydrate/protein interactions on the basis of microarrays will also be discussed.

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Abbreviations

Bn:

benzyl

Bz:

benzoyl

DIPEA:

diisopropylethylamine

DMF:

dimethylformamide

EDTA:

ethylenediaminetetraacetic acid

Fmoc:

9‑fluorenylmethoxycarbonyl

HBTU:

2‑(1H‑benzotriazole‐1‑yl)‐1,1,3,3‑tetramethyluronium hexafluorophosphate

HOBt:

1‑hydroxybenzotriazole

MALDI-TOF-MS:

matrix‐assisted laser desorption ionization mass spectrometry

MPEG:

polyethylene glycol monomethyl ether

MS:

molecular sieves

NIS:

N‑iodosuccinimide

PEG:

polyethylene glycol

TBAHS:

tetra‑n‑butylammonium hydrogen sulfate

TBDMS:

tert-butyldimethylsilyl

TBDPS:

tert-butyldiphenylsilyl

TFA:

trifluoroacetic acid

TMSOTf:

trimethylsilyl triflate

Troc:

2,2,2‑trichloroethoxycarbonyl

UDP:

uridine diphosphate

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Authors and Affiliations

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

    Katsunori Tanaka, Yukari Fujimoto, Shin-ichi Tanaka, Yasutaka Mori & Koichi Fukase

Authors
  1. Katsunori Tanaka
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  2. Yukari Fujimoto
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  3. Shin-ichi Tanaka
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  4. Yasutaka Mori
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  5. Koichi Fukase
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Corresponding author

Correspondence to Koichi Fukase .

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., Fujimoto, Y., Tanaka, Si., Mori, Y., Fukase, K. (2008). Combinatorial 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_28

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