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SialoGlyco Chemistry and Biology II pp 125–149Cite as

Sialoside Arrays: New Synthetic Strategies and Applications

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Part of the book series: Topics in Current Chemistry ((TOPCURRCHEM,volume 367))

Abstract

Sialic acid-containing carbohydrates, or sialosides, play critical roles in many biological events and in diseases, including viral and bacterial infections, the immune response, the progression of tumor cell metastasis, etc. Despite the importance, the limited access to complex sialosides had prevented extensive studies on the function and significance of sialic acid structural diversity. However, recent advances in synthetic sialoside chemistry, such as the novel chemoenzymatic or stereochemical approach, have produced homogeneous size- and structure-defined sialosides to create diverse sialosides for array application. The advantage of sialoside arrays is the multivalent display of arrayed sialosides which can serve to mimic cell surface display; thus, an array-based technique is well suited for investigations of the real sialoside-mediated interactions in nature. In brief, this chapter discusses the novel strategies for synthesizing sialosides with selected examples of applications to illustrate the potential of sialoside arrays and further forecast to the trend of using nanotechnology in sialoside arrays.

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Abbreviations

Ac:

Acetyl

Ac2O:

Acetic anhydride

AcOH:

Acetic acid

Bn:

Benzyl

Bz:

Benzoyl

Cbz:

Bezyloxycarbonyl

CMP:

Cytidine monophosphate

CSA:

Camphorsulfonic acid

DCM:

Dichloromethane

DMF:

N,N-Dimethylformamide

DMTST:

Dimethyl(methylthio)sulfonium trifluoromethanesulfonate

EA:

Ethyl acetate

ERBB:

Epidermal growth factor receptor

Et:

Ethyl

Gal:

Galactose

GalNAc:

N-Acetylgalactosamine

Glc:

Glucose

GlcNAc:

N-Acetylglucosamine

KDN:

Deaminoneuraminic acid

Man:

Mannose

ManNAc:

N-Acetylmannosamine

MeOH:

Methanol

MeOTf:

Methyl trifluoromethane sulfonate

NBz:

p-Nitrobenzoyl

Neu5Ac:

N-Acetylneuraminic acid

Neu5Gc:

N-Glycolylneuraminic acid

NIS:

N-Iodosuccinimide

Ph:

Phenyl

PhSOTf:

Phenyl sulfenyl triflate

RRVs:

Relative relativity values

RT:

Room temperature

SBox:

S-Benzoxazolyl

Siglec:

Sialic acid-binding immunoglobulin-type lectins

TfOH:

Trifluoromethanesulfonic acid

TMSOTf:

Trimethylsilyl trifluoromethanesulfonate

Tn:

GalNAcα-Ser/Thr; Tn is a precursor for many extended O-glycans in animal glycoproteins

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Authors and Affiliations

  1. Genomics Research Center, Academia Sinica, 128 Academia Road, Section 2, Nankang, Taipei, 115, Taiwan

    Chi-Hui Liang, Che-Hsiung Hsu & Chung-Yi Wu

Authors
  1. Chi-Hui Liang
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  2. Che-Hsiung Hsu
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  3. Chung-Yi Wu
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Correspondence to Chi-Hui Liang .

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Editors and Affiliations

  1. Institute for Cellular Chemistry, Hannover, Germany

    Rita Gerardy-Schahn

  2. Lille University of Science and Technology, Villeneuve d'Ascq Cedex, France

    Philippe Delannoy

  3. Institute for Glycomics, Griffith University, Southport, Queensland, Australia

    Mark von Itzstein

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Liang, CH., Hsu, CH., Wu, CY. (2014). Sialoside Arrays: New Synthetic Strategies and Applications. In: Gerardy-Schahn, R., Delannoy, P., von Itzstein, M. (eds) SialoGlyco Chemistry and Biology II. Topics in Current Chemistry, vol 367. Springer, Cham. https://doi.org/10.1007/128_2014_602

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