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By H. G. Davies, Ralph Green, D. R. Kelly and Stanley M. Roberts (Auth.)

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Additional info for Biotransformations in Preparative Organic Chemistry. The Use of Isolated Enzymes and Whole Cell Systems in Synthesis

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1. e. = 87%). NHCOMe C02H C02Me (122) NHCOMe (123) The reaction was easy to perform on a 3-g scale. In contrast to the popular use of PLE as a hydrolysing enzyme, Camboie and Klibanov [78] have developed an excellent method for the formation of optically active alcohols and esters from racemates via transesterification. g. alcohols) is low, then obviously the yield of transesterification products will be small. However, by utilizing a two-phase system, in which the enzyme is present in the aqueous phase and the ester and the alcohol are dissolved in the organic phase, Camboie and Klibanov have succeeded in preparing a number of optically active alcohols and their propionic esters.

HYDROLYSIS AND CONDENSATION REACTIONS 34 MeOaC-Λθ Me0 2 C-\ Q HuV-V,,H ^C02Me ^-C0 2 H (35) (36) o Me02C^ ^-C0 2 Me v Me02C^ (37) -C02H (38) Thus, with respect to the prochiral C (ß) atom bonded to an O atom, PLE cleaves the same ester group as in the case of 3-hydroxyglutarate but with much higher specificity. Since Mohr et al. had proposed elsewhere [34] (see later) that only substituents in the a and/or ß position (with respect to the ester group which is cleaved) are essential for selectivity during PLE hydrolysis, the epoxyester (39) was investigated.

Unfortunately, the ethyl and butyl diesters were hydrolysed much more slowly with a lot less stereoselectivity. 1. e. >98%), reactions on the allyl and butyl analogues exhibited extremely low selectivity. Lipases have been used for the hydrolysis of esters in prostaglandin chemistry. PPL has been proposed as the reagent of choice for the mild ester hydrolysis of sensitive prostaglandin derivatives [90]. The lipase was successfully used in the hydrolysis of the ester (131) when the acid (132) was ,(CH2)3C02R (CH2)3C02R (131) R = Me (132) R = H (133) R = Me (134) R = H obtained in 92% yield.

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