Biocatalytic Michael-Type Additions of Acetaldehyde to Nitroolefins with the Proline-Based Enzyme 4-Oxalocrotonate Tautomerase Yielding Enantioenriched γ-Nitroaldehydes

Call me Michaelase: The enzyme 4‐oxalocrotonate tautomerase (4‐OT) promiscuously catalyzes the Michael‐type addition of acetaldehyde to a collection of aromatic and aliphatic nitroolefins with high stereoselectivity producing precursors of γ‐aminobutyric acid (GABA) analogues (see scheme).

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Bibliographische Detailangaben
Veröffentlicht in:	Chemistry : a European journal 2013-10, Vol.19 (43), p.14407-14410
Hauptverfasser:	Geertsema, Edzard M., Miao, Yufeng, Tepper, Pieter G., de Haan, Pim, Zandvoort, Ellen, Poelarends, Gerrit J.
Format:	Artikel
Sprache:	eng
Schlagworte:	Acetaldehyde - chemistry Acetaldehyde - metabolism Alkenes - chemistry Alkenes - metabolism aminobutyric acid Biocatalysis C-C bond formation Carbon - chemistry enzymes gamma-Aminobutyric Acid - metabolism Isomerases - metabolism Michael-type addition Nitro Compounds - chemistry Proline - chemistry Stereoisomerism
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Beschreibung
Zusammenfassung:	Call me Michaelase: The enzyme 4‐oxalocrotonate tautomerase (4‐OT) promiscuously catalyzes the Michael‐type addition of acetaldehyde to a collection of aromatic and aliphatic nitroolefins with high stereoselectivity producing precursors of γ‐aminobutyric acid (GABA) analogues (see scheme).
ISSN:	0947-6539 1521-3765
DOI:	10.1002/chem.201302351