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?-Phenylalanine Ester Synthesis from Stable ?-Keto Ester Substrate Using Engineered ?-Transaminases.

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

SUBMITTER: Buß O 

PROVIDER: S-EPMC6100204 | biostudies-literature | 2018 May

REPOSITORIES: biostudies-literature

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

Buß Oliver O   Voss Moritz M   Delavault André A   Gorenflo Pascal P   Syldatk Christoph C   Bornscheuer Uwe U   Rudat Jens J  

Molecules (Basel, Switzerland) 20180518 5

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 benzoyla  ...[more]

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