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Solid-phase synthesis of an A-B loop mimetic of the Cepsilon3 domain of human IgE: macrocyclization by Sonogashira
Alan C Spivey1, John McKendrick, Ratnasothy Srikaran
1Department of Chemistry, University of Sheffield, Brook Hill, Sheffield S3 7HF, UK. a.c.spivey@imperial.ac.uk
Abstract:
The solid-phase synthesis of a cyclic peptide containing the 21-residue epitope found in the A-B loop of the Cepsilon3 domain of human immunoglobulin E has been carried out. The key macrocyclization step to form the 65-membered ring is achieved in approximately 15% yield via an "on-resin" Sonogashira coupling reaction which concomitantly installs a diphenylacetylene amino acid conformational constraint within the loop.
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