Access to α,α-Disubstituted Disilylated Amino Acids and Their Use in Solid-Phase Peptide Synthesis.
A concise synthetic pathway yielding to hydrophobic α,α-disubstituted disilylated amino acids based on a hydrosilylation reaction is described. As a first example of utilization in solid-phase peptide synthesis, TESDpg was introduced in replacement of Aib in an alamethicin sequence, leading to analogues with modified physicochemical properties and conserved helical structures. This study highlights the potential of these new amino acids as tools for peptide modulation.
Institut des Biomolécules Max Mousseron, IBMM, UMR-5247, CNRS, Université Montpellier, ENSCM , Place Eugène Bataillon, Montpellier34095 Cedex 5, France.
Roberto
R
Fanelli
Université de Perpignan Via Domitia , CRIOBE USR 3278, 58 avenue P. Alduy Bât T, 66860 Perpignan, France.
Khoubaib
K
Ben Haj Salah
Université de Perpignan Via Domitia , CRIOBE USR 3278, 58 avenue P. Alduy Bât T, 66860 Perpignan, France.
Nicolas
N
Inguimbert
CRM2 (UMR UL-CNRS 7036) Faculté des Sciences et Technologies, Université de Lorraine , 70239 Boulevard des Aiguillettes, 54506 Vandoeuvre-lès-Nancy, France.
Claude
C
Didierjean
Institut des Biomolécules Max Mousseron, IBMM, UMR-5247, CNRS, Université Montpellier, ENSCM , Place Eugène Bataillon, Montpellier34095 Cedex 5, France.
Jean
J
Martinez
Institut des Biomolécules Max Mousseron, IBMM, UMR-5247, CNRS, Université Montpellier, ENSCM , Place Eugène Bataillon, Montpellier34095 Cedex 5, France.
Florine
F
Cavelier
D000408:Alamethicin / Q000737:chemistry; D000596:Amino Acids / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D010455:Peptides / Q000138:chemical synthesis* / Q000737:chemistry; D012821:Silanes / Q000138:chemical synthesis* / Q000737:chemistry; D060327:Solid-Phase Synthesis Techniques; D013237:Stereoisomerism
D000596:Amino Acids; D010455:Peptides; D012821:Silanes; D000408:Alamethicin