title: Stereoselective synthesis and structural elucidation of dicarba peptides.
abstract: A facile stereoselective synthesis of cis and trans unsaturated dicarba peptides has been established using preformed diaminosuberic acid derivatives as bridging units. In addition, characteristic spectral differences in the (13)C-NMR spectra of the cis- and trans-isomers show that the chemical shift of carbons in the Δ4,5-diaminosuberic acid residue can be used to assign stereochemistry in unsaturated dicarba peptides formed from ring closing metathesis of linear peptide sequences.
authors.affiliation: School of Chemistry, Monash University, Clayton 3800, Victoria, Australia. andrea.robinson@monash.edu.
authors.forename: Ellen C
authors.initials: EC
authors.lastname: Gleeson
authors.affiliation: School of Chemistry, Monash University, Clayton 3800, Victoria, Australia. andrea.robinson@monash.edu.
authors.forename: Zhen J
authors.initials: ZJ
authors.lastname: Wang
authors.affiliation: Medicinal Chemistry, Monash Institute of Pharmaceutical Sciences, Monash University, 381 Royal Parade, Parkville 3052, Victoria, Australia.
authors.forename: Samuel D
authors.initials: SD
authors.lastname: Robinson
authors.affiliation: Medicinal Chemistry, Monash Institute of Pharmaceutical Sciences, Monash University, 381 Royal Parade, Parkville 3052, Victoria, Australia.
authors.forename: Sandeep
authors.initials: S
authors.lastname: Chhabra
authors.affiliation: Medicinal Chemistry, Monash Institute of Pharmaceutical Sciences, Monash University, 381 Royal Parade, Parkville 3052, Victoria, Australia.
authors.forename: Christopher A
authors.initials: CA
authors.lastname: MacRaild
authors.affiliation: School of Chemistry, Monash University, Clayton 3800, Victoria, Australia. andrea.robinson@monash.edu.
authors.forename: W Roy
authors.initials: WR
authors.lastname: Jackson
authors.affiliation: Medicinal Chemistry, Monash Institute of Pharmaceutical Sciences, Monash University, 381 Royal Parade, Parkville 3052, Victoria, Australia.
authors.forename: Raymond S
authors.initials: RS
authors.lastname: Norton
authors.affiliation: School of Chemistry, Monash University, Clayton 3800, Victoria, Australia. andrea.robinson@monash.edu.
authors.forename: Andrea J
authors.initials: AJ
authors.lastname: Robinson
mesh_terms: D066241:Carbon-13 Magnetic Resonance Spectroscopy; D010455:Peptides / Q000737:chemistry*; D011487:Protein Conformation; D013237:Stereoisomerism
chemical_list: D010455:Peptides