P. S. Hilaire, T. Lowary, and Morten Meldal
Dec 11, 1998
Citations
0
Influential Citations
48
Citations
Journal
Journal of the American Chemical Society
Abstract
Glycopeptides that mimic the action of oligosaccharides have been rapidly identified through the implementation of combinatorial library methodology combined with a novel, easy, screening and analysis method. A glycopeptide library containing three different glycosyl amino building blocks, Fmoc-Asn(β-Ac3GlcNAc)-OPfp (5), Fmoc-Thr(α-Ac4Man)-OPfp (6), and Fmoc-Thr[α-Ac4Man(1→3)α-2-O-Bz-4,6-Ac2Man]-OPfp (7), was synthesized by the portion-mixing method on PEGA solid support. The library was designed to facilitate rapid and unambiguous analysis of the active glycopeptides detected during the high throughput-screening step. Consequently, the library was synthesized using the ladder synthesis approach and linked to the solid support via a photolabile linker. The glycosyl amino acids were labeled with carboxylic acid tags to allow unambiguous identification of the glycan moiety. Photolytic release of active glycopeptide from the resin was induced by irradiation of the bead with the MALDI-TOF-MS laser, and analys...