Mots-cl es: Acylation Hydrolyse Lipases Groupe partant Esters de vinyle Esters de ph enyl ethyle Enantios electivit e a b s t r a c tWe have studied the effects of the acyl moiety on the enantioselectivity of three lipases: Candida antarctica B, Pseudomonas cepacia and Candida cylindracea, frequently used in kinetic resolutions by acylation or hydrolysis. The size of the acyl group was examined using various enol esters during the transesterification of 1-phenylethanol and the hydrolysis of the corresponding phenylethylesters. C. antarctica-B lipase showed the highest selectivity in the transesterification of 1-phenylethanol with isopropenyl and vinyl acetate, vinyl decanoate, vinyl laurate, (E > 200). The esters 1-phenyl -ethyl-acetate, decanoate and laurate are also hydrolyzed with high selectivities (E > 150) with CAL-B. The results can be correlated to the three-dimensional form of each lipase. The effect of the migrating group on the reactivity and selectivity of the lipases are discussed for both reactions. r é s u m é Nous avons etudi e les effets du fragment acyle sur l' enantios electivit e de trois lipases : Candida antarctica B, Pseudomonas cepacia et Candida cylindracea, fr equemment utilis ees dans les d edoublements cin etiques par acylation ou hydrolyse. La taille du groupe acyle a et e examin ee en utilisant divers esters d' enols dans l'acylation du 1-ph enyl ethanol et par hydrolyse des phenylethylesters correspondants. La lipase de C. antarctica-B a montr e une haute s electivit e (E > 200) lors de la transest erification du 1-ph enyl ethanol avec de l'ac etate d'isoprop enyle, l'ac etate de vinyle, le d ecanoate de vinyle, le laurate de vinyle. Avec cette lipase (CAL-B), les esters 1-ph enyl ethyl-ac etate, d ecanoate et laurate sont hydrolys es avec des s electivit es elev ees (E > 150). Les r esultats peuventêtre corr el es a la forme tridimensionnelle de chaque lipase. Pour les deux r eactions, l'effet de la nature du groupe partant sur la r eactivit e et la s electivit e des lipases est discut e.

This study reports the lipase-catalyzed resolution of heteroaromatic secondary alcohols by succinic anhydride under different activation conditions by convenient procedure with succinic anhydride. The effects of succinic anhydride and the nature of the heteroatom are discussed in standard conditions in the kinetic resolution with lipases. The results recorded under microwave activation and ultrasonication is compared. (R)-4-chromanol was obtained in optically pure form (ee > 99%) with a high selectivity E > 200 by Pseudomonas cepacia lipase (PCL) in diethyl ether, using microwave radiation and under ultrasonication. The reaction time is reduced compared to the conventional heating with a better control of the selectivity of the lipase PCL. A significant effect of the nature of the heteroatoms on the reactivity and selectivity of the lipase with succinic anhydride has been disclosed, regardless the conditions of activation. This method proved to be clean, fast, interesting alternative, and facilitates the use of a cyclic anhydride, by microwave or ultrasound especially with secondary alcohols. The process is a valuable prerequisite for the preparative scale production of enantiomerically heteroaromatic alcohols in sustainable chemistry.

"Chicken viscera" constitute very abundant domestic wastes interestingly investigated in the present paper. The efficiency of this crude slaughter co-product of high protein component, as biocatalyst, for the hydrolysis of fatty acid esters was reported and that, without any pre-treatment. The crude Chicken Intestines Powder (CIP) has shown a high reactivity for the hydrolysis of fatty esters. Two biocatalyst preparations were independently explored for the bioresolution of sec-phenyl alkyl carbinol esters: the CIP preparation and the crude Chicken Intestines Acetone Powder CIAP ​​preparation. The last one has shown good catalytic activity during the bio-hydrolysis in biphasic medium. Furthermore, the direct hydrolysis of milk fat using CIAP (500 mg) reveals the elimination of fats present in 50 ml of treated milk. These results open up very interesting prospects for the use of this biowaste for the treatment of milk fat.