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Solid-phase synthesis of an A-B loop mimetic of the C epsilon 3 domain of human IgE: macrocyclization by Sonogashira coupling

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Spivey, A.C., McKendrick, J.E. ORCID: https://orcid.org/0000-0003-2275-0569, Srikaran, R. and Helm, B.A. (2003) Solid-phase synthesis of an A-B loop mimetic of the C epsilon 3 domain of human IgE: macrocyclization by Sonogashira coupling. Journal of Organic Chemistry, 68 (5). pp. 1843-1851. ISSN 0022-3263

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To link to this item DOI: 10.1021/jo026693e

Abstract/Summary

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 similar to15% yield via an "on-resin" Sonogashira coupling reaction which concomitantly installs a diphenylacetylene amino acid conformational constraint within the loop.

Item Type:Article
Refereed:Yes
Divisions:Interdisciplinary centres and themes > Chemical Analysis Facility (CAF) > Mass Spectrometry (CAF)
Life Sciences > School of Chemistry, Food and Pharmacy > Department of Chemistry
ID Code:11632
Uncontrolled Keywords:EPSILON-RI-ALPHA, HECK REACTION, AMINO-ACIDS, OLIGO(1,4-PHENYLENE ETHYNYLENE)S, SECONDARY STRUCTURE, PROTEIN INTERFACES, PEPTIDE-SYNTHESIS, IMMUNOGLOBULIN-E, AROMATIC-AMINES, FC
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