Synthesis and Enzymatic Conversion of Amino Acids Equipped with the Silanetriol Functionality: A Prelude to Silicon Biodiversification - Archive ouverte HAL
Article Dans Une Revue ChemistryEurope Année : 2023

Synthesis and Enzymatic Conversion of Amino Acids Equipped with the Silanetriol Functionality: A Prelude to Silicon Biodiversification

Jade Dussart‐gautheret
Julie Rivollier
  • Fonction : Auteur
Cédric Simon
  • Fonction : Auteur
Alessandro de Simone
Jérôme Berthet
  • Fonction : Auteur
Stéphanie Delbaere
Régina Maruchenko
  • Fonction : Auteur
Claire Troufflard
Denis Lesage
Yves Gimbert
  • Fonction : Auteur
Gilles Lemière
Philippe Marlière
Louis Fensterbank

Résumé

Synthetic routes are reported for the three analogues of the simplest L‐2‐amino‐dicarboxylic acids, aspartate, glutamate, and aminoadipate, in which the silanetriol group (Si(OH) 3 ) replaces the distal carboxyl group (CO 2 H). Direct access to the silanetriol amino acids relied either on catalytic hydrosilylation of a terminal alkene using triethoxysilane, or on alkylation of a glycine equivalent anion by triallyl(iodomethyl)silane. In both cases, acid hydrolysis afforded the silanetriol amino acids. These were shown to self‐assemble into siloxane Si‐O clusters as their concentration in water increased in the pH range of 1–12. Such reversible cross‐linking did not prevent silanetriol amino acids from serving as substrates of an aminotransferase enzyme, boding well for their utilization as microbial nutrients to encompass silicon in future stages of metabolism and polypeptide edifices.

Domaines

Chimie
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Dates et versions

hal-04297355 , version 1 (21-11-2023)

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Citer

Jade Dussart‐gautheret, Julie Rivollier, Cédric Simon, Alessandro de Simone, Jérôme Berthet, et al.. Synthesis and Enzymatic Conversion of Amino Acids Equipped with the Silanetriol Functionality: A Prelude to Silicon Biodiversification. ChemistryEurope, 2023, ⟨10.1002/ceur.202300058⟩. ⟨hal-04297355⟩
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