359781-97-8Relevant articles and documents
Fullerene l -Amino Acids and Peptides: Synthesis under Phase-Transfer Catalysis Using a Phosphine-Borane Linker. Electrochemical Behavior
Minois, Pauline,Bayardon, Jér?me,Meunier-Prest, Rita,Jugé, Sylvain
, p. 11358 - 11369 (2017)
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 γ-iodo-α-amino ester reagents under phase-transfer catalysis (PTC). Second, a sec-phosphine borane amino ester was saponified and coupled with α, γ-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 C60-amino acid or dipeptide derivatives in yields up to 80% by P-C bond formation. This addition reaction which proceeds in mild and moderate dilute conditions (0.03 M) leads to [60]fullerene derivatives as epimeric mixtures (～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 C60-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 C60-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.
Structural design and synthesis of bimodal PNA that simultaneously binds two complementary DNAs to Form fused double duplexes
Gupta, Manoj Kumar,Madhanagopal, Bharath Raj,Datta, Dhrubajyoti,Ganesh, Krishna N.
, p. 5255 - 5260 (2020/07/16)
Bimodal PNAs are new PNA constructs designed to bind two different cDNA sequences synchronously to form double duplexes. They are synthesized on solid phase using sequential coupling and click reaction to introduce a second base in each monomer at Cα via alkyltriazole linker. The ternary bimodal PNA:DNA complexes show stability higher than that of individual duplexes. Bimodal PNAs are appropriate to create higher-order fused nucleic acid assemblies.
Nα-Fmoc-protected ω-azido- and ω-alkynyl-L- amino acids as building blocks for the synthesis of "clickable" peptides
Isaad, Alexandra Le Chevalier,Barbetti, Francesca,Rovero, Paolo,D'Ursi, Anna Maria,Chelli, Mario,Chorev, Michael,Papini, Anna Maria
experimental part, p. 5308 - 5314 (2009/06/18)
The growing interest in the 1,4-disubstituted-1,2,3-triazolyl moiety as an amide bond surrogate and its formation through very mild, chemoselective, and bioorthogonal CuI-catalyzed Huisgen 1,3-dipolar [3+2] cycloaddition of an alkynyl to an azi
