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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| Veröffentlicht in: | Chemistry : a European journal 2013-10, Vol.19 (43), p.14407-14410 |
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| container_end_page | 14410 |
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| container_issue | 43 |
| container_start_page | 14407 |
| container_title | Chemistry : a European journal |
| container_volume | 19 |
| creator | Geertsema, Edzard M. Miao, Yufeng Tepper, Pieter G. de Haan, Pim Zandvoort, Ellen Poelarends, Gerrit J. |
| description | 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). |
| doi_str_mv | 10.1002/chem.201302351 |
| format | Article |
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| fulltext | fulltext |
| identifier | ISSN: 0947-6539 |
| ispartof | Chemistry : a European journal, 2013-10, Vol.19 (43), p.14407-14410 |
| issn | 0947-6539 1521-3765 |
| language | eng |
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| source | MEDLINE; Wiley Journals |
| subjects | 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 |
| title | Biocatalytic Michael-Type Additions of Acetaldehyde to Nitroolefins with the Proline-Based Enzyme 4-Oxalocrotonate Tautomerase Yielding Enantioenriched γ-Nitroaldehydes |
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