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Biocatalytic Michael-type additions of acetaldehyde to nitroolefins with the proline-based enzyme 4-oxalocrotonate tautomerase yielding enantioenriched γ-nitroaldehydes.

Chemistry. 2013; 
Geertsema EM, Miao Y, Tepper PG, de Haan P, Zandvoort E, Poelarends GJ.
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Gene Synthesis … See SI for details. 19. Synthetic 4-OT was purchased from GenScript USA Inc.(Piscataway, NY). For folding of chemically synthesized 4-OT into active homohexamer see: MC Fitzgerald, I. Chernushevich, KG Standing, SBH Kent, CP Whitman, J. Am. Chem. Soc … Get A Quote

摘要

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.,Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

关键词

C-C bond formation; Michael-type addition; aminobutyric acid; biocatalysis; enzymes
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