摘要 |
Compounds that are synthetically inexpensive to make relative to the naturally occuring selectin ligands and that retain selectin binding activity are described that have a three-dimensionally stable configuration for sialic acid and fucose, or analogs or derivatives of these groups, such that sialic acid and fucose are separated by a non-carbohydrate linker that permits binding between those groups and the selectins, such compounds being represented by general structural formula I(a) wherein m and n are independently an integer of from 1 to 5, Y and Z are independently a connecting moiety selected from the group consisting of -CH2-, -O-, -S-, -NR' and -NR'R"-(wherein R' and R" are independently H or an alkyl containing 1 to 4 carbon atoms); X is a connecting moiety which is selected from the group consisting of -O-, -S- and -N-; and -R''' may be -R'' or any moiety which does not interfere with the three-dimensional configuration of A or B so as to interfere with selectin binding and is preferably a moiety selected from the group consisting of -OR'', -SR'', -I, -N3, and -NR'R'', and A is selected from the group consisting of alpha and beta forms of sialic acid, Kemp's acid, Quinic acid, Glyceric acid, Lactic acid and acetic acid, and esters thereof and B is selected from the group consisting of alpha and beta forms of L-Fucose and esters and substituted forms thereof wherein one or more of the -OH groups is independently -F, or -NR<IV>, R<V> wherein R<IV> and R<V> are independently an alkyl containing 1 to 5 carbons.
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