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Solid-Phase Azopeptide Diels-Alder Chemistry for Aza-pipecolyl Residue Synthesis To Study Peptide Conformation.
- Source :
-
The Journal of organic chemistry [J Org Chem] 2019 May 17; Vol. 84 (10), pp. 6006-6016. Date of Electronic Publication: 2019 Apr 26. - Publication Year :
- 2019
-
Abstract
- Solid-phase chemistry for the synthesis and Diels-Alder reaction of Fmoc-protected azopeptides has been developed and used to construct aza-pipecolyl (azaPip) peptides. Considering their ability to induce electronic and structural constraints that favor cis-amide isomer geometry and type VI β-turn conformation in model peptides, azaPip residues have now been introduced into biologically relevant targets by this enabling synthetic method. Turn conformers were shown to be important for receptor affinity, selectivity, and activity by employing azaPip residues to study the conformational requirements of opioid and cluster of differentiation 36 receptor peptide ligands.
Details
- Language :
- English
- ISSN :
- 1520-6904
- Volume :
- 84
- Issue :
- 10
- Database :
- MEDLINE
- Journal :
- The Journal of organic chemistry
- Publication Type :
- Academic Journal
- Accession number :
- 30957495
- Full Text :
- https://doi.org/10.1021/acs.joc.8b03283