Syntheses of two trimannose analogs each containing C-mannosyl or 5-thio-C-mannosyl residue: their affinities to concanavalin A

O Tsuruta; H Yuasa; S Kurono; H Hashimoto

doi:10.1016/s0960-894x(99)00087-6

Syntheses of two trimannose analogs each containing C-mannosyl or 5-thio-C-mannosyl residue: their affinities to concanavalin A

Bioorg Med Chem Lett. 1999 Mar 22;9(6):807-10. doi: 10.1016/s0960-894x(99)00087-6.

Authors

O Tsuruta¹, H Yuasa, S Kurono, H Hashimoto

Affiliation

¹ Department of Life Science, Faculty of Bioscience and Biotechnology, Tokyo Institute of Technology, Yokohama, Japan.

PMID: 10206540
DOI: 10.1016/s0960-894x(99)00087-6

Abstract

C-Mannosyl residue-containing trimannose ManC alpha(1,6)[Man alpha(1,3)Man] (2) and 5-thio-C mannosyl residue-containing trimannose 5SManC alpha(1,6)[Man alpha(1,3)Man] (3) were synthesized via a glycosyl radical addition to enone derivative of mannose (6). Dissociation constants for the binding of these trisaccharides to concanavalin A (ConA) were determined by a fluorescence anisotropy inhibition assay: Kd = 198 and 31 microM, respectively. The unexpectedly large Kd value for the compound 2 compared with the compound 3 and the natural trimannose 1 demonstrates a characteristic of C-glycoside.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Concanavalin A / chemistry*
Kinetics
Mannose / analogs & derivatives*
Mannose / chemical synthesis
Models, Chemical
Protein Binding

Substances

Concanavalin A
Mannose