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Solid-phase Synthesis of [4.4] Spirocyclic Oximes
Published on: February 6, 2019
Parallel Synthesis of Sialyl Lewis X Mimetics on a Solid Phase: Access to a Library of Fucopeptides
Thomas F J Lampe1, Gabriele Weitz-Schmidt2, Chi-Huey Wong1
1The Scripps Research Institute, Department of Chemistry, 10550 North Torrey Pines Road, La Jolla, CA 92037 (USA), Fax: (+1) 619-784-2409.
Abstract:
A novel anchoring group p-(acyloxymethyl)benzylidene acetal (p-AMBA) enables the bidirectional functionalization of glycosylated amino acid derivatives and thus the rapid parallel synthesis of fucopeptides as sialyl Lewis X mimetics on a solid phase [Eq. (a), PEG-PS=poly(ethylene glycol) graft copolymer]. This led to the discovery of new mimetics against P-selectin with IC50 values in the low μM range.
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