Parallel synthesis of glycomimetic libraries: targeting a C-type lectin.
We have developed methods for the parallel synthesis of two libraries of non-carbohydrate-based analogues of mannose on a solid support. The natural product shikimic acid was used as a key building block. The ability of the compounds to block the binding of the C-type lectin MBP-A to a mannosylated surface was assessed in a high-throughput assay. Ten library members with inhibitory activities equivalent to that of alpha-methyl mannopyranoside were identified. [reaction: see text]
Schuster
Michael C
MC
Departments of Chemistry and Biochemistry, University of Wisconsin-Madison, Madison, WI 53706, USA.
Mann
David A
DA
Buchholz
Tonia J
TJ
Johnson
Kathryn M
KM
Thomas
William D
WD
Kiessling
Laura L
LL
D040761:Biomimetic Materials / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism; D020650:Combinatorial Chemistry Techniques; D037181:Lectins, C-Type / Q000737:chemistry* / Q000378:metabolism; D008358:Mannose / Q000031:analogs & derivatives* / Q000737:chemistry / Q000378:metabolism; D037601:Mannose-Binding Lectin / Q000737:chemistry / Q000378:metabolism; D018716:Molecular Mimicry; D012765:Shikimic Acid / Q000737:chemistry
D037181:Lectins, C-Type; D037601:Mannose-Binding Lectin; C069858:mannose binding protein A; D012765:Shikimic Acid; D008358:Mannose