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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3) Cyclic diesters show higher stereoselectivity than the corresponding acyclic analogues. (4) Substituents of different polarity and different size show opposite effects on selectivity of the enzymic hydrolysis. For example, while the compounds (27) and (44) are hydrolysed with pro-(S) specificity (vide supra), for the compounds (29) and (62) the pro-(Ä) group is preferentially attacked. HO s^-\J202Me (CH2)„T ^-^C02H HO (62) (63) n = 1 (64) n = 2 (CH 2 )J ^-^COaMe (65) n = 3 (66) « = 4 Cyclic weso-diesters have been shown [48] to be excellent intermediates for the enzymic syntheses of useful chiral bicyclic lactones.

After 4 days reaction the (S)-( + )-sulcatol obtained had an enantiomeric excess >99% and the (R)-( — )-sulcatol [produced via chemical hydrolysis of the recovered butyrate (127)] was ca. 80% optically pure. The advantages gained by using dehydrated PPL and 2,2,2-trifluoroethyl laurate for this process have been described [84]. O II H7C3CQ Me MeCH(OH)CH2CH2CH=CMe2 X W (CH2)2CH=CMe2 Ester interchange, catalysed by PPL in organic solvents and involving vinyl esters, such as vinyl butyrate, and primary or secondary alcohols, shows promise because the reverse reaction is virtually impossible [85].

2— Hydrolysis and Condensation Reactions In this Section the enzyme catalysed hydrolysis reactions of esters, amides, epoxides and nitriles are reviewed. The formation of esters and amides using enzymes is also discussed. 1. 1. CLEAVAGE AND FORMATION OF CARBOXYLIC ACID ESTER BONDS Esterases and Lipases Of the wide range of esterases available commercially, very few have been widely utilized in organic transformations. C. C. C. 1); others, such as the lipase from the yeast Candida cylindracea, are gaining popularity.

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Biotransformations in Preparative Organic Chemistry. The Use by H. G. Davies, Ralph Green, D. R. Kelly and Stanley M.
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