Simple and efficient solid-phase synthesis of unprotected peptide aldehyde for peptide segment ligation

Dominique Lelièvre (1) , Hadjila Chabane (1) , Agnès F. Delmas (1)

1 CBM - Centre de biophysique moléculaire

We describe an efficient solid-phase synthesis of C-terminal peptide aldehyde. Making use of the stability of the PAM linker towards both acid and base conditions, a pentapeptide was synthesized starting from a PAM resin according to Fmoc/tBu chemistry. The side-chains were deprotected by TFA. The peptide was cleaved by aminolysis with aminoacetaldehyde-dimethylacetal leading to a C-terminal masked aldehyde. The unprotected peptide aldehyde was then coupled to amino-oxy derivatives by chemoselective ligation in aqueous solution.

Domaines: Sciences du Vivant [q-bio]

Dominique Lelièvre, Hadjila Chabane, Agnès F. Delmas. Simple and efficient solid-phase synthesis of unprotected peptide aldehyde for peptide segment ligation. Tetrahedron Letters, 1998, 39 (52), pp.9675-9678. ⟨10.1016/S0040-4039(98)02267-9⟩. ⟨hal-02146742⟩