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Issue 13, 2017
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Inter- and intramolecular aldol reactions promiscuously catalyzed by a proline-based tautomerase

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Abstract

The enzyme 4-oxalocrotonate tautomerase (4-OT), which in nature catalyzes a tautomerization step as part of a catabolic pathway for aromatic hydrocarbons, was found to promiscuously catalyze different types of aldol reactions. These include the self-condensation of propanal, the cross-coupling of propanal and benzaldehyde, the cross-coupling of propanal and pyruvate, and the intramolecular cyclizations of hexanedial and heptanedial. Mutation of the catalytic amino-terminal proline (P1A) greatly reduces 4-OT's aldolase activities, whereas mutation of another active site residue (F50A) strongly enhances 4-OT's aldolase activities, indicating that aldolization is an active site process. This catalytic promiscuity of 4-OT could be exploited as starting point to create tailor-made, artificial aldolases for challenging self- and cross-aldolizations.

Graphical abstract: Inter- and intramolecular aldol reactions promiscuously catalyzed by a proline-based tautomerase

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Publication details

The article was received on 08 Feb 2017, accepted on 02 Mar 2017 and first published on 02 Mar 2017


Article type: Paper
DOI: 10.1039/C7OB00302A
Citation: Org. Biomol. Chem., 2017,15, 2809-2816
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    Inter- and intramolecular aldol reactions promiscuously catalyzed by a proline-based tautomerase

    M. Rahimi, E. M. Geertsema, Y. Miao, J. van der Meer, T. van den Bosch, P. de Haan, E. Zandvoort and G. J. Poelarends, Org. Biomol. Chem., 2017, 15, 2809
    DOI: 10.1039/C7OB00302A

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