Promiscuous Catalysis of Asymmetric Michael-Type Additions of Linear Aldehydes to β-Nitrostyrene by the Proline-Based Enzyme 4-Oxalocrotonate Tautomerase

Exploiting catalytic promiscuity: The proline‐based enzyme 4‐oxalocrotonate tautomerase (4‐OT) promiscuously catalyzes asymmetric Michael‐type additions of linear aldehydes—ranging from acetaldehyde to octanal—to trans‐β‐nitrostyrene in aqueous solvent. The presence of 1.4 mol % of 4‐OT effected for...

Ausführliche Beschreibung

Gespeichert in:

Bibliographische Detailangaben
Veröffentlicht in:	Chembiochem : a European journal of chemical biology 2013-01, Vol.14 (2), p.191-194
Hauptverfasser:	Miao, Yufeng, Geertsema, Edzard M., Tepper, Pieter G., Zandvoort, Ellen, Poelarends, Gerrit J.
Format:	Artikel
Sprache:	eng
Schlagworte:	Aldehydes - chemistry Aldehydes - metabolism biocatalysis Catalysis catalytic promiscuity Isomerases - chemistry Isomerases - metabolism Michael addition Models, Molecular nitroaldehydes Proline - chemistry Proline - metabolism Styrenes - chemistry Styrenes - metabolism tautomerases
Online-Zugang:	Volltext
Tags:	Tag hinzufügen Keine Tags, Fügen Sie den ersten Tag hinzu!

Beschreibung
Zusammenfassung:	Exploiting catalytic promiscuity: The proline‐based enzyme 4‐oxalocrotonate tautomerase (4‐OT) promiscuously catalyzes asymmetric Michael‐type additions of linear aldehydes—ranging from acetaldehyde to octanal—to trans‐β‐nitrostyrene in aqueous solvent. The presence of 1.4 mol % of 4‐OT effected formation of the anticipated γ‐nitroaldehydes in fair to good yields with dr values of up to 93:7 and ee values of up to 81 %.
ISSN:	1439-4227 1439-7633
DOI:	10.1002/cbic.201200676