[60]Fullerene l -Amino Acids and Peptides: Synthesis under Phase-Transfer Catalysis Using a Phosphine–Borane Linker. Electrochemical Behavior

Abstract : A new method to link amino acid and peptide derivatives to [60]fullerene is described. It uses hydrophosphination with a secondary phosphine borane. First, the stereoselective synthesis of secondary phosphine borane amino acid derivatives was achieved by alkylation of phenylphosphine borane with gamma-iodo-alpha-amino ester reagents under phase transfer catalysis (PTC). Second, a sec-phosphine borane amino ester was saponified and coupled with alpha,gamma-diamino esters to afford the corresponding dipeptide derivatives in good yields. Finally, the hydrophosphination reaction of [60]fullerene by the sec-phosphine borane compounds was performed under PTC to obtain C-60-amino acid or dipeptide derivatives in yields up to 80% by PC bond formation. This addition reaction which proceeds in mild and moderate dilute conditions (0.03 M) leads to [60]fullerene derivatives as epimeric mixtures (similar to 1:1) due to the P-chirogenic center but without racemization of the amino acid or peptide moiety. In addition, the electrochemical behavior of a C-60-phosphine borane amino ester was investigated by cyclic voltammetry and spectroelectrochemistry after controlled-potential electrolysis. It showed evidence for the retro-hydrophosphination reaction into free [60]fullerene and sec-phosphine borane amino ester compound. Consequently, the synthesis of sec-phosphine borane amino acids followed by their use in hydrophosphination reactions of [60]fullerene under phase-transfer catalysis has demonstrated a great utility for the preparation of C-60-derivatives. Indeed, the hydrophosphination and the retro-hydrophosphination reactions of [60]fullerene/phosphine borane compounds offer a promising new strategy for the reversible immobilization of amino acid or peptide derivatives on carbon nanomaterials such as [60]fullerene.
Type de document :
Article dans une revue
Journal of Organic Chemistry, American Chemical Society, 2017, 82 (21), pp.11358 - 11369. 〈http://pubs.acs.org/doi/abs/10.1021/acs.joc.7b01737〉. 〈10.1021/acs.joc.7b01737〉
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Soumis le : lundi 11 décembre 2017 - 12:45:20
Dernière modification le : vendredi 8 juin 2018 - 14:50:12

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Pauline Minois, Jérome Bayardon, Rita Meunier-Prest, Sylvain Jugé. [60]Fullerene l -Amino Acids and Peptides: Synthesis under Phase-Transfer Catalysis Using a Phosphine–Borane Linker. Electrochemical Behavior. Journal of Organic Chemistry, American Chemical Society, 2017, 82 (21), pp.11358 - 11369. 〈http://pubs.acs.org/doi/abs/10.1021/acs.joc.7b01737〉. 〈10.1021/acs.joc.7b01737〉. 〈hal-01660740〉

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