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Creating a new benzaldehyde lyase for atom-economic synthesis of chiral 1,2,4-butanetriol and 2-aminobutane-1,4-diol from formaldehyde

机译:Creating a new benzaldehyde lyase for atom-economic synthesis of chiral 1,2,4-butanetriol and 2-aminobutane-1,4-diol from formaldehyde

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摘要

While formaldehyde is an emerging C1 resource for the synthesis of high value-added chemicals due to its high and versatile reactivity, selective activation and controllable transformation of formalde-hyde still remains a great challenge. In particular, coupling of form-aldehyde with small aldehydes such as 3-hydroxypropanal offers excellent opportunity for constructing valuable molecules but has not been realized. A benzaldehyde lyase from Herbiconiux sp. SALV-R1 was engineered through directed evolution to achieve the coupling of 3-hydroxypropanal and formaldehyde. A carbonyl reductase and a transaminase were identified to catalyze reduction or transamination of 1,4-dihydroxybutan-2-one, a highly functional-ized small ketone. The newly attained enzymatic hydroxymethyla-tion and asymmetric reduction or transamination were then combined with the chemocatalytic hydration of acrolein in a one -pot process to synthesize optically pure 1,2,4-butanetriol and 2-aminobutane-1,4-diol from acrolein and formaldehyde. These re-sults exemplify a new way for sustainable synthesis of high value-added chemicals from C1 molecules and simple starting materials.

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