title: Synthesis and evaluation of eight-membered cyclic pseudo-dipeptides.
abstract: In the course of the development of calpain inhibitors, we report the synthesis of eight-membered cyclic pseudo dipeptides closely related to the known inhibitor SJA6017. The ring closure was effected by metathesis of the diallyl-substituted dipeptides 6 and 7. The formation of the dipeptides under kinetic control leads to the preferential formation of the unlike diastereomer 7 over the like diastereomer 6. The relative configuration of the diastereomers was determined by NMR and modeling studies of the related cyclic compounds 8 and 9 and their derivatives. The compounds proved not to inhibit calpain.
authors.affiliation: Department of Chemistry, University of Canterbury, Private Bag 4800, Christchurch, New Zealand. andrew.abell@canterbury.ac.nz
authors.forename: Andrew D
authors.initials: AD
authors.lastname: Abell
authors.forename: Karina M
authors.initials: KM
authors.lastname: Brown
authors.forename: James M
authors.initials: JM
authors.lastname: Coxon
authors.forename: Matthew A
authors.initials: MA
authors.lastname: Jones
authors.forename: Sigeru
authors.initials: S
authors.lastname: Miyamoto
authors.forename: Axel T
authors.initials: AT
authors.lastname: Neffe
authors.forename: Janna M
authors.initials: JM
authors.lastname: Nikkel
authors.forename: Blair G
authors.initials: BG
authors.lastname: Stuart
mesh_terms: D002154:Calpain / Q000037:antagonists & inhibitors; D019295:Computational Biology; D004151:Dipeptides / Q000138:chemical synthesis* / Q000737:chemistry; D008958:Models, Molecular; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D010456:Peptides, Cyclic / Q000138:chemical synthesis* / Q000737:chemistry; D011487:Protein Conformation
chemical_list: D004151:Dipeptides; C109145:N-(4-fluorophenylsulfonyl)-L-valyl-L-leucinal; D010456:Peptides, Cyclic; D002154:Calpain