MULTIVALENT LIGANDS FOR THE MANNOSE-SPECIFIC LECTIN ON TYPE-1 FIMBRIAE OF ESCHERICHIA-COLI - SYNTHESES AND TESTING OF TRIVALENT ALPHA-D-MANNOSIDE CLUSTERS

The syntheses of the triantennary cluster alpha-D-mannosides 16, 19, 2 3 and 24 and their capacities to inhibit mannose-dependent binding of E, call HE 101 (pPK14) are described. The cluster glycosides are forme d by glycosylation of tris-(3-hydroxypropyl)nitromethane 13, and by li nking of suitable mannoside derivatives via amide and thiourea bonds t o tris-(2-carboxyethyl)nitromethane 17 and tris-(2-aminoethyl)amine 20 . Functionalized mannosides are attached to the core molecules at the 6-position of the sugar ring to allow variation of the introduced agly cone moieties in order to compare their effects on the inhibitory pote ncies of the derived mannoside clusters. The B-peptide-bridged cluster mannoside 19 displays the highest binding potency towards the type 1 fimbrial lectin of E. coli as tested by inhibition agglutination tests and ELISA.