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Amino Acid Derivatives of Tetrathiafulvalene and Their N-H center dot center dot center dot O Peptide Bond Dipoles-Templated Solid State Assemblies

Abstract :

We report on a series of amino acid derivatives of tetrathiafulvalene as well as on the structure-directing abilities of their peptide residues in the crystalline solid state to stabilize patterns of interactions such as beta strands and sheet motifs. Characteristic hydrogen-bonding motifs are indeed identified within ethylenedithiotetrathiafulvalene (EDT-TTF) and dimethyltetrathiafulvalene (Me-2-TTF) based compounds 1-5. Esters 1-3 contain hydrogen-bond acceptors, namely carbonyl groups, as well as one strong (NH) and one weak (C-sp(2)-H) hydrogen-bond donor. In addition to the hydrogen-bonded sets of ester derivatives, acids 4 and 5 present the carboxylic acid moiety, which acts as both a hydrogen-bond donor and acceptor. EDT-TTF-CO-GlyOH has been previously used to afford a new type of hydrogen-bonded acid/zwitterion (1:1) hybrid admixture of redox peptidics.

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https://hal.univ-angers.fr/hal-03344547
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Soumis le : mercredi 15 septembre 2021 - 10:11:13
Dernière modification le : jeudi 9 décembre 2021 - 15:46:06
Archivage à long terme le : : jeudi 16 décembre 2021 - 18:19:07

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Abdelkrim El-Ghayoury, Leokadiya Zorina, Sergey Simonov, Lionel Sanguinet, Patrick Batail. Amino Acid Derivatives of Tetrathiafulvalene and Their N-H center dot center dot center dot O Peptide Bond Dipoles-Templated Solid State Assemblies. European Journal of Organic Chemistry, 2013, 5, pp.921-928. ⟨10.1002/ejoc.201201330⟩. ⟨hal-03344547⟩

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