Sunday, July 26, 2009
P25

Green pea and cucumber extracts as biocatalysts in the reduction of phenylpropanone

Aida Solis, Karen Bustillo, Abraham Cano, Herminia I. Perez, Norberto Manjarrez, and Julia Cassani. Sistemas Biológicos, Universidad Autónoma Metropolitana, Calz. del Hueso No. 1100, México, Mexico

The asymmetric reduction of ketones is one of the most important and practical procedures for the preparation of non-racemic chiral alcohols, which can be transformed into various functionalities, to synthesize industrially important chemicals such as pharmaceuticals, agrochemicals and natural products. The catalysts for the asymmetric reduction of ketones can be chemical and biological. Among the biocatalytic methodologies to obtain chiral alcohols, asymmetric bioreduction of prochiral ketones is preferred because it can give 100% theoretical yield. In this study we used, separately, the fruit and the peel of green pea and cucumber to catalyze the reduction of phenylpropanone to 1-phenylpropanol; one of the advantages of these biocatalyst sources are their easy availability and low cost, mainly the peel since this part of the fruit is considered as waste. Methodology: The biological material was blended with water (1g biological material and 1mL water), then centrifuged and filtered, the supernatant was mixed with a solution of phenylpropanone in DMF, the mixture was stirred at 25°C for 24 h. Conversion % was determined by GC and enantiomeric excess by chiral HPLC. The fruit and the peel of cucumber and green pea fruit showed highly activity since the conversions to 1-phenylpropanol were 50, 70 and 55% respectively, whereas the conversion with the green pea fruit was 20% after 48h. However the enantioselectivity did not follow the same pattern, with the green pea fruit the ee was >99%, but with the rest of the biocatalyst sources the ee was < 10%.

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