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β-Phenylalanine Ester Synthesis from Stable β-Keto Ester Substrate Using Engineered ω-Transaminases

Buß, Oliver; Voss, Moritz; Delavault, André; Gorenflo, Pascal; Syldatk, Christoph; Bornscheuer, Uwe; Rudat, Jens

The successful synthesis of chiral amines from ketones using ω-transaminases has been shown in many cases in the last two decades. In contrast, the amination of β-keto acids is a special and relatively new challenge, as they decompose easily in aqueous solution. To avoid this, transamination of the more stable β-keto esters would be an interesting alternative. For this reason, ω-transaminases were tested in this study, which enabled the transamination of the β-keto ester substrate ethyl benzoylacetate. Therefore, a ω-transaminase library was screened using a coloring o-xylylenediamine assay. The ω-transaminase mutants 3FCR_4M and ATA117 11Rd show great potential for further engineering experiments aiming at the synthesis of chiral (S)- and (R)-β-phenylalanine esters. This alternative approach resulted in the conversion of 32% and 13% for the (S)- and (R)-enantiomer, respectively. Furthermore, the (S)-β-phenylalanine ethyl ester was isolated by performing a semi-preparative synthesis

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Verlagsausgabe §
DOI: 10.5445/IR/1000082981
Veröffentlicht am 22.05.2018
DOI: 10.3390/molecules23051211
Zitationen: 4
Web of Science
Zitationen: 3
Cover der Publikation
Zugehörige Institution(en) am KIT Institut für Bio- und Lebensmitteltechnik (BLT)
Publikationstyp Zeitschriftenaufsatz
Publikationsjahr 2018
Sprache Englisch
Identifikator ISSN: 1420-3049
KITopen-ID: 1000082981
Erschienen in Molecules
Band 23
Heft 5
Seiten Article: 1211
Bemerkung zur Veröffentlichung Gefördert durch den KIT-Publikationsfonds
Vorab online veröffentlicht am 18.05.2018
Schlagwörter β-phenylalanine ethyl ester; β-amino acid; ω-transaminase; asymmetric synthesis
Nachgewiesen in Scopus
Web of Science
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