@article{Offermann:2012:10.1021/jo202604q,
author = {Offermann, DA and McKendrick, JE and Sejberg, JJP and Mo, B and Holdom, MD and Helm, BA and Leatherbarrow, RJ and Beavil, AJ and Sutton, BJ and Spivey, AC},
doi = {10.1021/jo202604q},
journal = {J Org Chem},
title = {Synthesis and Incorporation into Cyclic Peptides of Tolan Amino Acids and Their Hydrogenated Congeners: Construction of an Array of A-B-loop Mimetics of the Cε3 Domain of Human IgE.},
url = {http://dx.doi.org/10.1021/jo202604q},
year = {2012}
}

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TY  - JOUR
AB  - The disruption of the human immunolobulin E-high affinity receptor I (IgE-FcεRI) protein-protein interaction (PPI) is a validated strategy for the development of anti asthma therapeutics. Here, we describe the synthesis of an array of conformationally constrained cyclic peptides based on an epitope of the A-B loop within the Cε3 domain of IgE. The peptides contain various tolan (i.e., 1,2-biarylethyne) amino acids and their fully and partially hydrogenated congeners as conformational constraints. Modest antagonist activity (IC(50) ∼660 μM) is displayed by the peptide containing a 2,2'-tolan, which is the one predicted by molecular modeling to best mimic the conformation of the native A-B loop epitope in IgE.
AU  - Offermann,DA
AU  - McKendrick,JE
AU  - Sejberg,JJP
AU  - Mo,B
AU  - Holdom,MD
AU  - Helm,BA
AU  - Leatherbarrow,RJ
AU  - Beavil,AJ
AU  - Sutton,BJ
AU  - Spivey,AC
DO  - 10.1021/jo202604q
PY  - 2012///
TI  - Synthesis and Incorporation into Cyclic Peptides of Tolan Amino Acids and Their Hydrogenated Congeners: Construction of an Array of A-B-loop Mimetics of the Cε3 Domain of Human IgE.
T2  - J Org Chem
UR  - http://dx.doi.org/10.1021/jo202604q
ER  - 

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