alpha,alpha'-disubstituted amino acids with silylated side chains as lipophilic building blocks for the synthesis of peptaibol analogues.
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.
Cavelier
Florine
F
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
Marchand
Damien
D
Martinez
Jean
J
D017646:Organosilicon Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D054848:Peptaibols / Q000138:chemical synthesis*; D011392:Proline / Q000031:analogs & derivatives / Q000737:chemistry; D013237:Stereoisomerism
D017646:Organosilicon Compounds; D054848:Peptaibols; C455420:silaproline; D011392:Proline