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Synthesis of 1,1-linked galactosyl mannosides carrying a thiazine ring as mimetics of sialyl lewis x antigen: Investigation of the effect of carboxyl group orientation on p-selectin inhibition

Academic Article
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Overview

authors

  • Shibata, K.
  • Hiruma, K.
  • Kanie, O.
  • Wong, Chi-Huey

publication date

  • 2000

journal

  • Journal of Organic Chemistry  Journal

abstract

  • This paper describes the synthesis of 1,1-linked galactosyl mannosides as sialyl Lewis X mimetics that contain a spiro-ring to position the carboxylate group in a well-defined orientation. It was found that compound 4 is more active as a P-selectin inhibitor (IC50 = 19 microM) than the parent disaccharide 2, which contains a flexible carboxyl group (IC50 = 193 microM). This result is consistent with that observed in the previous NMR study of sialyl Lewis X bound to P-selectin. The chemistry described here should be useful for the development of selective inhibitors of E-, P-, and L-selectins.

subject areas

  • Carbohydrate Sequence
  • Magnetic Resonance Spectroscopy
  • Mannosides
  • Molecular Sequence Data
  • Oligosaccharides
  • P-Selectin
  • Polysaccharides
  • Thiazines
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Identity

International Standard Serial Number (ISSN)

  • 0022-3263

Digital Object Identifier (DOI)

  • 10.1021/jo991556b

PubMed ID

  • 10789451
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Additional Document Info

start page

  • 2393

end page

  • 2398

volume

  • 65

issue

  • 8

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