First Application of the Dakin-West Reaction to Fmoc Chemistry: Synthesis of the ketomethylene tripeptide Fmoc-Nα-Asp(tBu)-(R,S)Tyr(tBu)Ψ(CO-CH2)Gly-OH

Joseph Richard Casimir (1) , Céline Turetta (1) , Laurent Ettouati (1) , Joëlle Paris (1)

1 UCBL ISPB - Université Claude Bernard Lyon 1 - Institut des Sciences Pharmaceutiques et Biologiques

A practical synthesis of a tripeptide containing a ketomethylene isostere, suitably protected for introduction in Fmoc SPPS, has been carried out for the first time in Fmoc chemistry by using a modified Dakin-West reaction.

Domaines: Chimie thérapeutique

Joseph Richard Casimir, Céline Turetta, Laurent Ettouati, Joëlle Paris. First Application of the Dakin-West Reaction to Fmoc Chemistry: Synthesis of the ketomethylene tripeptide Fmoc-Nα-Asp(tBu)-(R,S)Tyr(tBu)Ψ(CO-CH2)Gly-OH. Tetrahedron Letters, 1995, 36 (27), pp.4797-4800. ⟨10.1016/0040-4039(95)00869-E⟩. ⟨hal-01333228⟩