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Synlett 2003(9): 1331-1333
DOI: 10.1055/s-2003-40330
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

Synthetic Analogs of the Lewisb-Tetrasaccharide and their Binding to Griffonia Simplicifolia Lectin-Part II

Vivekanand Kamath, Ole Hindsgaul*
Department of Chemistry, University of Alberta, Edmonton, Alberta, T6G 2G2, Canada
e-Mail: ole.hindsgaul@ualberta.ca;
Further Information

Publication History

Received 12 March 2003
Publication Date:
30 June 2003 (online)

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Abstract

The lewis b tetrasaccharide is known to bind to lectin IV of Griffonia simplicifolia. In an effort to prepare superior ligands, we have synthesized analogs of this tetrasaccharide and evaluated their binding to the lectin. This paper (part II in a series of two) describes the synthesis of and binding studies with analogs where the GlcNAc unit (a) has been replaced by simpler mimicking residues that are both flexible and rigid. A simple 1,2-trans cyclohexanediol residue provided a reasonable simplified inhibitor whereas a flexible 1,2-ethanediol replacement led to a completely inactive ligand.

Key words

lewis b tetrasaccharide - lectins - galactose unit

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1H NMR (D2O): 1. δ: 4.09 (q, 1 H, H-5b), 4.31 (q, 1 H, H-5c), 4.57 (d, 1 H, H-1a), 4.93 (d, 1 H, H-1b), 5.23 (d, 1 H, H-1c); 2. δ: 4.48 (q, 1 H, H-5d), 4.56 (d, 1 H, H-1b), 4.70 (q, 1 H, H-5c), 4.99 (d, 1 H, H-1c), 5.28 (d, 1 H, H-1d); 3a. δ: 4.35 (d, 1 H, H-5d), 4.52 (d, 1 H, H-1b), 4.60 (q, 1 H, H-5c), 5.00 (d, 1 H, H-1c), 5.28 (d, 1 H, H-1d); 3b. δ: 4.57 (d, 1 H, H-1b), 4.73 (q, 1 H, H-5c), 4.91 (d, 1 H, H-1c), 5.27 (d, 1 H, H-1d).