title: alpha,alpha'-disubstituted amino acids with silylated side chains as lipophilic building blocks for the synthesis of peptaibol analogues.
abstract: New alpha,alpha'-disubstituted amino acids with silylated side chains have been synthesized in racemic form. Starting from a Schiff base of glycine tert-butyl ester, a large variety of alpha,alpha'-dialkylated amino acids has been obtained, depending on the alkylating reagents. The application of a hydrosilylation methodology enabled the synthesis of the same unnatural amino acids in an enantiomerically pure form. The ability of these bulky amino acids to be incorporated into peptides by solution-phase methodology has also been demonstrated, since constrained silylated dipeptides have been synthesized. These new lipophilic building blocks could be useful and innovative in the design of peptaibol analogues.
authors.affiliation: Institut des Biomolécules Max Mousseron, UMR-CNRS 5247, Universités de Montpellier I et II, Place Eugène Bataillon, F-34095 Montpellier Cedex 05, France. florine@univ-montp2.fr
authors.forename: Florine
authors.initials: F
authors.lastname: Cavelier
authors.forename: Damien
authors.initials: D
authors.lastname: Marchand
authors.forename: Jean
authors.initials: J
authors.lastname: Martinez
mesh_terms: D017646:Organosilicon Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D054848:Peptaibols / Q000138:chemical synthesis*; D011392:Proline / Q000031:analogs & derivatives / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D017646:Organosilicon Compounds; D054848:Peptaibols; C455420:silaproline; D011392:Proline