Sunday, July 26, 2009
P27

Dehydrated plants as biocatalyst for the hydrolysis of 1-phenylpropanol acetate

Aida Solis, Laura Bernáldez, Araceli Hernández, Norberto Manjarrez, Herminia I. Pérez, and Héctor Luna. Sistemas Biológicos, Universidad Autónoma Metropolitana, Calz. del Hueso No. 1100, DF, Mexico

Hydrolases are biocatalysts widely used to prepare optically active alcohols. Most of the hydrolases are from microbial and animal origin. However plant enzymes have rarely been employed for synthetic purposes, but these enzymes are very attractive due to their low cost, readily availability and ease of handling. From a previous study about the hydrolytic activity of acetone dried plants, were chosen the plants that gave the best results to find the reaction conditions, pH and cosolvents, which improve the conversion and enantioselectivity of the 1-phenylpropanol (1) obtained from the hydrolysis of 1-phenylpropanol acetate (2).

Methodology: Plants were blended with acetone, filtered and let dry; the powder was used without any other purification. The plant powder was suspended in a buffer solution (0.1M, pH 5, 6, 7 or 8), the acetate in a cosolvent (acetonitrile, dioxane, DMSO, DMF and THF) was added, the mixture was stirred at 25°C for 48 h, conversion was determined by GC and ee by chiral HPLC. Results are shown in Table 1. The configuration of the main enantiomer was “S”.

Table 1. Effect of pH and cosolvent on the conversion and ee of 1

Plant

pH

Cosolvent

% Conv(1)   %ee(1)

Capulín seed (Prunus capuli)

5

Dioxane

      26              70

Cherry seed (Prunus avium)

5

DMSO

      45              81

Red plum seed (Prunus domestica, cv moscatel)

5

DMSO

      10              67

Almond seed (Prunus dulcis)

5

DMSO

      14              64

Tomatillo fruit (Physalis peruviana)

7

acetonitrile

      22              55

Pitahaya leaves (Hylocereus undatus)

7

acetonitrile

      19              63