Download PDF by Giorgio Colombo, Gianluca Ottolina, Giacomo Carrea (auth.),: Biocatalysis

By Giorgio Colombo, Gianluca Ottolina, Giacomo Carrea (auth.), Prof. Dr. Herfried Griengl (eds.)

ISBN-10: 321183527X

ISBN-13: 9783211835272

ISBN-10: 3709163102

ISBN-13: 9783709163108

The publication includes in its first half experiences on modelling of enzyme homes in natural solvents, lipase-catalysed synthesis of carboxylic amides, chemoenzymatic synthesis of lipidated peptides and chemoenzymatic differences in nucleoside chemistry. within the moment half contributions on fresh advancements in biocatalysis are given: lipase and esterase catalysed resolutions, investigations on regio- and stereoselective biocatalytic acylations in steroid side-chains and of substrate- and stereospecificity of Penicillin G amidases, deracemisation for amino acid synthesis, biocatalytic hydrolysis of nitriles, enzymatic and microbial hydroxylation of dienes and alpha-methyl esters, enantioselective sulphoxidations by means of peroxidases.

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1. Reaction mechanism of lipase catalysis; the numbering is for Candida antarctica lipase, - - - - - denotes a hydrogen bond; step (iii) is the microscopic reversal of steps (i) and (ii) Lipase-Catalyzed Synthesis of Amides 25 Although lipases have not been designed for enantioselectivity, they are chiral and, hence, inherently enantioselective towards all components of the reaction: the acyl group, the leaving group, and the nucleophile. The resolution of chiral amines is one of the major practical applications of lipase-catalyzed aminolysis.

Showed that the lipase-catalyzed reaction of butyric acid and ammonia is quite feasible [48]; these authors have also established the parameters of the equilibria involved [49]. The lipase-catalyzed condensation of carboxylic acids with hydroxylamine and hydrazine [20, 32a, 50] as well as their derivatives [20] presents a special case because of the stability of the resulting amide bond. These reactions proceed readily to essentially quantitative conversions (Table 2); the condensation of octanoic acid and hydroxylamine has even be performed in water [20].

71] Solvents often exert dramatic effects on enzymatic resolutions [74], and an inversion of the enantiopreference has even been observed in certain cases . The effect of the solvent on the CaLB mediated condensation of ibuprofen and hydroxylamine to (R)-ibuproxam (2, R = OH) was only modest, however [19]. E ranged from a value of 4 in water and some moderately hydrophilic solvents via 8 in isooctane or tert-butyl alcohol to 13 in dioxane. The enantiomer discrimination in the CaLB-catalyzed ammoniolysis of phenylglycine methyl ester (Fig.

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Biocatalysis by Giorgio Colombo, Gianluca Ottolina, Giacomo Carrea (auth.), Prof. Dr. Herfried Griengl (eds.)


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