Mono-substitution of symmetric diesters: Selectivity of: Mycobacterium smegmatis acyltransferase variants

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Abstract

A method for selectively reacting one, out of two identical carboxylic esters in a symmetric diester has been developed. An esterase from Mycobacterium smegmatis (MsAcT) has a restricted active site resulting in a narrow acyl donor specificity. This constraint was used to develop a selective synthesis route from divinyl adipate (a symmetric diester) towards mixed vinyl adipate esters. To find a suitable catalyst, the wild type (wt) MsAcT and two MsAcT variants: A single point mutant (L12A) and a double point mutant (T93A/F154A), were immobilized and studied under solvent-free conditions. Out of the tested catalysts, MsAcT L12A was the most selective for mono-Transesterification of divinyl adipate. When divinyl adipate was reacted with 1.5 equivalents of a hydroxyl vinyl ether full conversion of DVA was observed yielding over 95% mixed diester. Furthermore, the limitations for longer dicarboxylic esters were studied, showing that MsAcT T93A/F154A tolerated up to at least dimethyl sebacate.

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Finnveden, M., Semlitsch, S., He, O., & Martinelle, M. (2019). Mono-substitution of symmetric diesters: Selectivity of: Mycobacterium smegmatis acyltransferase variants. Catalysis Science and Technology, 9(18), 4920–4927. https://doi.org/10.1039/c9cy01181a

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