Synthesis and molecular recognition of carbohydrate-centered multivalent glycoclusters by a plant lectin RCA120

Yongjun Gao, Atsuko Eguchi, Kazuaki Kakehi, Yuan C. Lee

Research output: Contribution to journalArticle

Abstract

Water soluble and lectin-recognizable carbohydrate-centered glycoclusters were prepared efficiently by the Huisgen 1,3-cycloaddition reaction of methyl-2,3,4,6-tetra-O-propargyl β-d-galactopyranoside with 2-azidoethyl glycosides of lactose and N-acetyllactosamine. Their binding by a plant lectin RCA120 was examined by capillary affinity electrophoresis using fluorescence-labeled asialoglycans from human α1-acid glycoprotein. The glycoclusters showed 400-fold stronger inhibitory effect than free lactose, manifesting strong multivalency effect.

Original languageEnglish (US)
Pages (from-to)6151-6157
Number of pages7
JournalBioorganic and Medicinal Chemistry
Volume13
Issue number22
DOIs
StatePublished - Nov 15 2005

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Keywords

  • 1,3-Cycloaddition reaction
  • Glycocluster
  • Lectin RCA
  • Molecular recognition

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Medicine
  • Molecular Biology
  • Pharmaceutical Science
  • Drug Discovery
  • Clinical Biochemistry
  • Organic Chemistry

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