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Design, synthesis and biological evaluation of aryl-substituted sialyl lewis x mimetics prepared via cross-metathesis of c-fucopeptides

Academic Article
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Overview

authors

  • Huwe, C. M.
  • Woltering, T. J.
  • Jiricek, J.
  • Weitz-Schmidt, G.
  • Wong, Chi-Huey

publication date

  • May 1999

journal

  • Bioorganic & Medicinal Chemistry  Journal

abstract

  • Several aryl substituted C-fucopeptides have been developed as sialyl Lewis X mimetics. Although the compounds have a much simpler structure compared to SLe(x), up to 3-times higher binding affinity toward E-selectin and > 1000 times toward P-selectin was observed. Furthermore, a convenient strategy for generating a number of analogues from a SLe(x) mimetic template at a very late stage of the synthesis was introduced, using a ruthenium catalyzed cross olefin metathesis under benchtop conditions.

subject areas

  • Carbohydrate Sequence
  • Drug Design
  • Fucose
  • Inhibitory Concentration 50
  • Models, Chemical
  • Molecular Sequence Data
  • Oligosaccharides
  • Peptides
  • Selectins
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Identity

International Standard Serial Number (ISSN)

  • 0968-0896

Digital Object Identifier (DOI)

  • 10.1016/s0968-0896(98)00245-4

PubMed ID

  • 10400330
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Additional Document Info

start page

  • 773

end page

  • 788

volume

  • 7

issue

  • 5

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