title: Stereoselective synthesis of original spirolactams displaying promising folded structures.
abstract: Access to diastereoisomeric forms of original spirolactam frameworks and investigation of their folded potentials are depicted here. Taking advantage of a stereoselective ring-contraction reaction, the Transannular Rearrangement of Activated Lactams (TRAL), followed by two unprecedented tandem reactions, we describe here an efficient access to elegant spirocyclic scaffolds. After dimerization, NMR analyses, circular dichroism, SEM and molecular modelling indicated the existence of an attractive edifice able to fold and behave as a PPII helix, a common yet neglected peptidic secondary structure.
authors.affiliation: Institut des Biomolécules Max Mousseron, IBMM UMR 5247 CNRS-Université Montpellier I-Université Montpellier II, Pl. E. Bataillon, 34095 Montpellier Cedex 5, France.
authors.forename: Guilhem
authors.initials: G
authors.lastname: Chaubet
authors.forename: Thibault
authors.initials: T
authors.lastname: Coursindel
authors.forename: Xavier
authors.initials: X
authors.lastname: Morelli
authors.forename: Stéphane
authors.initials: S
authors.lastname: Betzi
authors.forename: Philippe
authors.initials: P
authors.lastname: Roche
authors.forename: Yannick
authors.initials: Y
authors.lastname: Guari
authors.forename: Aurélien
authors.initials: A
authors.lastname: Lebrun
authors.forename: Loïc
authors.initials: L
authors.lastname: Toupet
authors.forename: Yves
authors.initials: Y
authors.lastname: Collette
authors.forename: Isabelle
authors.initials: I
authors.lastname: Parrot
authors.forename: Jean
authors.initials: J
authors.lastname: Martinez
mesh_terms: D040761:Biomimetic Materials / Q000138:chemical synthesis* / Q000737:chemistry*; D060326:Chemistry Techniques, Synthetic; D007769:Lactams / Q000138:chemical synthesis* / Q000737:chemistry*; D008958:Models, Molecular; D008968:Molecular Conformation; D010455:Peptides / Q000737:chemistry; D017433:Protein Structure, Secondary; D013237:Stereoisomerism; D013379:Substrate Specificity
chemical_list: D007769:Lactams; D010455:Peptides; C011083:polyproline