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

Abstract : 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.
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https://hal.archives-ouvertes.fr/hal-02146742
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Submitted on : Tuesday, June 4, 2019 - 11:20:00 AM
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Dominique Lelièvre, Hadjila Chabane, Agnès F. Delmas. Simple and efficient solid-phase synthesis of unprotected peptide aldehyde for peptide segment ligation. Tetrahedron Letters, Elsevier, 1998, 39 (52), pp.9675-9678. ⟨10.1016/S0040-4039(98)02267-9⟩. ⟨hal-02146742⟩

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