NDLI: 2-Oxabutane as a substitute for internal monomer units of oligosaccharides to create lectin ligands

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2-Oxabutane as a substitute for internal monomer units of oligosaccharides to create lectin ligands

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Organic & Biomolecular Chemistry Vol - 9 Issue - 9

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2-Oxabutane as a substitute for internal monomer units of oligosaccharides to create lectin ligands

Content Provider	Royal Society of Chemistry (RSC)
Author	Yuasa, Hideya Kawada, Yuki Yang, Li-Ying Kubota, Daijiro Bai, Lina
Copyright Year	2011
Abstract	The synthesis of bioactive oligosaccharides is too tedious to scale up for commercialization. However, structurally simplified glycomimetics are commercializable, if they can be synthesized much more easily than the oligosaccharides while having a comparable bioactivity. In this study, we propose a 2-oxabutane (OB) structure as an imitation of the internal monosaccharide units in oligosaccharides. Two trimannoside and three pentamannoside OB-glycomimics were synthesized in remarkably short steps. Among them, Manα1-OB-2Man 10, a trimannoside mimic, showed eight-fold affinity toward concanavalin A (ConA) relative to methyl mannoside in latex agglutination lectin assay and equilibrium dialysis assay (EDA), while the other mimics showed three- to four-fold affinities. EDA indicated that the bindings between each mimic molecule and a ConA subsite were all in one-to-one stoichiometry and thus these mimics were monovalent ligands, excluding multivalence effect for the high affinities. The strong affinity of 10 could be explained by the occupation of two mannose binding sites of a ConA subsite by its two mannose units. Mimic 10 proved to be even a better ligand for ConA than the natural disaccharide Manα1,2Man, while been much more easy to synthesize, thereby illustrating the potential of the approach here presented.
Starting Page	6579
Ending Page	6586
Page Count	8
File Format	HTM / HTML PDF
ISSN	14770520
Volume Number	9
Issue Number	19
Journal	Organic & Biomolecular Chemistry
DOI	10.1039/c1ob05775h
Language	English
Publisher	Royal Society of Chemistry
Access Restriction	Open
Subject Keyword	Lectin Stoichiometry Ligand Mannose Concanavalin A Latex Disaccharide Mimicry Hemagglutination OB Monosaccharide Electronic design automation Dialysis
Content Type	Text
Resource Type	Article
Subject	Organic Chemistry Biochemistry Physical and Theoretical Chemistry

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Structural basis of carbohydrate recognition by a man(a1-2)man-specific lectin from bowringia milbraedii (2006).

A Latex Agglutination Test for Lectin binding

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2-Oxabutane as a substitute for internal monomer units of oligosaccharides to create lectin ligands

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2-Oxabutane as a substitute for internal monomer units of oligosaccharides to create lectin ligands