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

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

doi:10.1016/j.bmc.2005.06.036

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

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

School of Medicine

Research output: Contribution to journal › Article › peer-review

46 Scopus citations

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 language	English (US)
Pages (from-to)	6151-6157
Number of pages	7
Journal	Bioorganic and Medicinal Chemistry
Volume	13
Issue number	22
DOIs	https://doi.org/10.1016/j.bmc.2005.06.036
State	Published - Nov 15 2005

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

Access to Document

10.1016/j.bmc.2005.06.036

Cite this

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title = "Synthesis and molecular recognition of carbohydrate-centered multivalent glycoclusters by a plant lectin RCA120",

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.",

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AU - Gao, Yongjun

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AU - Kakehi, Kazuaki

AU - Lee, Yuan C.

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