Download Biocatalysis by Giorgio Colombo, Gianluca Ottolina, Giacomo Carrea (auth.), PDF
By Giorgio Colombo, Gianluca Ottolina, Giacomo Carrea (auth.), Prof. Dr. Herfried Griengl (eds.)
The booklet comprises in its first half studies on modelling of enzyme homes in natural solvents, lipase-catalysed synthesis of carboxylic amides, chemoenzymatic synthesis of lipidated peptides and chemoenzymatic alterations in nucleoside chemistry. within the moment half contributions on contemporary 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 way of peroxidases.
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Waldmann Enzyme-labile Protecting Groups in the Synthesis of Lipidated Peptides For the synthesis of lipidated peptides and proteins, the lability of the thioester under basic conditions and towards nucleophiles poses a considerable problem. Furthermore, under acidic conditions addition of the acid to the prenyl group double bonds readily occurs. The combination of both lipid modifications, prenyl and S-acyl groups, dramatically limits the number of usable protecting groups. The acid lability of the prenyl groups (Scheme 1) excludes the application of ten-butyl and benzyl-type functions.
Lipases, the lipid hydrolyzing catalysts of nature, are eminently suited for such an approach because of their stability and the simplicity of their catalytic machinery (Fig. 1). These characteristics have made them outstanding catalysts for synthetic biotransformations that involve the carboxyl group, such as esterification, transesterification, * Corresponding author H. ), Biocatalysis © Springer-Verlag Wien 2000 24 F. van Rantwijk et al. perhydrolysis, and aminolysis in which the natural nucleophile (water) is replaced by alcohols, hydroperoxides, or amines [2, 3].
The more hindered and less flexible amine 13 behaved similarly to 11e upon acylation by acetic acid esters in the presence of CaLB: the enantiodiscrimination was modest when the ethyl ester was used as donor but, quite remarkably, absolute with the isopropyl ester ; BcL was much less selective, although the same trend became apparent. 6 It should be noted that 13 has two chiral centres; the acylation yields  indicate that only one (presumable that attached to the nitrogen atom) was resolved.