Solid-phase synthesis of an A-B loop mimetic of the Cepsilon3 domain of human IgE: macrocyclization by Sonogashira coupling.
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.
Spivey
Alan C
AC
Department of Chemistry, University of Sheffield, Brook Hill, Sheffield S3 7HF, UK. a.c.spivey@imperial.ac.uk
McKendrick
John
J
Srikaran
Ratnasothy
R
Helm
Birgit A
BA
D000595:Amino Acid Sequence; D002384:Catalysis; D003500:Cyclization; D006801:Humans; D007073:Immunoglobulin E / Q000737:chemistry*; D007139:Immunoglobulin epsilon-Chains / Q000737:chemistry*; D007202:Indicators and Reagents; D008958:Models, Molecular; D018716:Molecular Mimicry; D019906:Nuclear Magnetic Resonance, Biomolecular; D010456:Peptides, Cyclic / Q000138:chemical synthesis* / Q000737:chemistry; D019032:Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
D007139:Immunoglobulin epsilon-Chains; D007202:Indicators and Reagents; D010456:Peptides, Cyclic; D007073:Immunoglobulin E