Formaldehyde as a Promising C1 Source: The Instrumental Role of Biocatalysis for Stereocontrolled Reactions

Sarah Desmons (1, 2) , Régis Fauré (2) , Sébastien Bontemps (1)

1 LCC - Laboratoire de chimie de coordination
2 TBI - Toulouse Biotechnology Institute

In the context of the depletion of fossil resources, formaldehyde is an emerging C-1 source exhibiting high and versatile reactivity, in comparison to the most studied C-1 molecules (CO2, CO, HCOOH, and CH4). In the present mini-review, we show that biocatalysis is an ideal approach to control the reactivity of formaldehyde and to use its great potential as a platform for the synthesis of value-added chiral products. The ability of aldolases and ThDP-dependent enzymes to catalyze stereocontrolled carbon-carbon bond formation with formaldehyde are shown to involve aldol and umpolung reactivity. The synergetic combination of (i) enzyme discovery, (ii) mechanistic understanding, and (iii) enzyme engineering provides highly stereospecific biocatalysts of increasing interest for synthetic chemistry.

Mots clés: enzyme; formaldehyde; aldolization; oxomethane; biocatalysis; cascade; carbohydrate; selectivity; carbon-carbon bond formation; umpolung reaction

Mots clés: enzyme; formaldéhyde; ressource fossile; biocatalyse

Domaines: Autre; Catalyse; Chimie organique; Biotechnologies; Biochimie, Biologie Moléculaire

Sarah Desmons, Régis Fauré, Sébastien Bontemps. Formaldehyde as a Promising C1 Source: The Instrumental Role of Biocatalysis for Stereocontrolled Reactions. ACS Catalysis, 2019, 9 (10), pp.9575-9588. ⟨10.1021/acscatal.9b03128⟩. ⟨hal-02330241⟩