2. Academic Validation
  3. Bicyclic tripeptide mimetics with reverse turn inducing properties

Bicyclic tripeptide mimetics with reverse turn inducing properties

  • J Med Chem. 1999 Feb 25;42(4):601-8. doi: 10.1021/jm981077p.
P Johannesson 1,  G Lindeberg,  W Tong,  A Gogoll,  A Karlén,  A Hallberg
Affiliations

Affiliation

  • 1 Department of Organic Pharmaceutical Chemistry, Uppsala University, Box 574, SE-751 23 Uppsala, Sweden.
PMID: 10052967 DOI: 10.1021/jm981077p
Abstract

Analogues of the hypertensive octapeptide angiotensin II, comprising novel constrained 5,8-bicyclic and 5,9-bicyclic tripeptide units adopting nonclassical beta-turn geometries, as deduced from theoretical conformational analysis, have been synthesized. Spontanous bicyclization upon acid-catalyzed deprotection of a model peptide, encompassing a protected omega-formyl alpha-amino acid in position 5 and cysteine residues in positions 3 and 7, revealed a strong preference for bicyclization toward the C-terminus. The bicyclic thiazolidine related angiotensin II analogues synthesized exhibited no affinity for the angiotensin II AT1 Receptor.

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