Solid-phase synthesis of an A-B loop mimetic of the Cepsilon3 domain of human IgE: macrocyclization by Sonogashira coupling

Alan C Spivey; John McKendrick; Ratnasothy Srikaran; Birgit A Helm

doi:10.1021/jo026693e

Solid-phase synthesis of an A-B loop mimetic of the Cepsilon3 domain of human IgE: macrocyclization by Sonogashira coupling

J Org Chem. 2003 Mar 7;68(5):1843-51. doi: 10.1021/jo026693e.

Authors

Alan C Spivey¹, John McKendrick, Ratnasothy Srikaran, Birgit A Helm

Affiliation

¹ Department of Chemistry, University of Sheffield, Brook Hill, Sheffield S3 7HF, UK. a.c.spivey@imperial.ac.uk

PMID: 12608800
DOI: 10.1021/jo026693e

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.

Publication types

Comparative Study
Research Support, Non-U.S. Gov't

MeSH terms

Amino Acid Sequence
Catalysis
Cyclization
Humans
Immunoglobulin E / chemistry*
Immunoglobulin epsilon-Chains / chemistry*
Indicators and Reagents
Models, Molecular
Molecular Mimicry
Nuclear Magnetic Resonance, Biomolecular
Peptides, Cyclic / chemical synthesis*
Peptides, Cyclic / chemistry
Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization
Stereoisomerism
Structure-Activity Relationship

Substances

Immunoglobulin epsilon-Chains
Indicators and Reagents
Peptides, Cyclic
Immunoglobulin E