title: Bending rigid molecular rods: formation of oligoproline macrocycles.
abstract: Bent but not broken: cyclic oligoprolines are accessed in a reaction that effectively bends rigid oligoproline peptides (see scheme; TBDMS=tert-butyldimethylsilyl). The stitching is accomplished during macrocyclization enabled by aziridine aldehydes and isocyanides. Molecular modeling studies suggest that electrostatic attraction between the termini of the linear peptide is pivotal for macrocyclization. The macrocycles were studied by circular dichroism with a polyproline II structure being observed in larger macrocycles.
authors.affiliation: Davenport Research Laboratories, Department of Chemistry, University of Toronto, Ontario, Canada.
authors.forename: Conor C G
authors.initials: CC
authors.lastname: Scully
authors.forename: Vishal
authors.initials: V
authors.lastname: Rai
authors.forename: Gennadiy
authors.initials: G
authors.lastname: Poda
authors.forename: Serge
authors.initials: S
authors.lastname: Zaretsky
authors.forename: Darcy C
authors.initials: DC
authors.lastname: Burns
authors.forename: R Scott
authors.initials: RS
authors.lastname: Houliston
authors.forename: Tiantong
authors.initials: T
authors.lastname: Lou
authors.forename: Andrei K
authors.initials: AK
authors.lastname: Yudin
mesh_terms: D002942:Circular Dichroism; D003500:Cyclization; D047028:Macrocyclic Compounds / Q000737:chemistry*; D009842:Oligopeptides / Q000737:chemistry*; D017646:Organosilicon Compounds / Q000737:chemistry*; D010455:Peptides / Q000737:chemistry*
chemical_list: D047028:Macrocyclic Compounds; D009842:Oligopeptides; D017646:Organosilicon Compounds; D010455:Peptides; C009660:t-butyldimethylsilyl compounds; C011083:polyproline