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

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

The ebook comprises in its first half experiences on modelling of enzyme houses in natural solvents, lipase-catalysed synthesis of carboxylic amides, chemoenzymatic synthesis of lipidated peptides and chemoenzymatic adjustments 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 way of peroxidases.

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PPL was specific for donors with L-configuration [44], whereas the enantiomeric preference towards the acceptor was generally slight [42, 45] (Table 1). These results should be interpreted with some caution, because crude PPL is known to contain protease and carboxylesterase contaminants which, in principle, could be the origin of the observed activity [43]. CrL, which was much less active than PPL, preferentially converted donors with D-configuration [44]. Table 1. PPL mediated dipeptide synthesis Donor Ac-N-L-Phe-OEtCl Ac-N -L-Phe-OEtCl Z-L-Phe-OMe Z-L-Phe-OMe Bz-N-L-Tyr-OEt Bz-N-L- Tyr-OEt Acceptor L-Leu-NH2 D-Leu-NH2 L-Ala-OBu s D-Ala-OBus L-Thr-OMe D-Thr-OMe Solvent Toluene Toluene Et20 Et20 3-Me-pentanol 3-Me-pentanol Product Time (h) N-Ac-L-Phe-L-Leu-NH 2 72 N-Ac-L-Phe-D-Leu-NH2 >72 Z-L-Phe-L-Ala-OBu s 16 Z-L-Phe-D-Ala-OBu s 16 Bz-N-L-Tyr-L-Thr-OMe 7 Bz-N-L-Tyr-D-Thr-OMe 7 Yield Ref.

HCys(Far)OMe (4) butyryl EEDQ,98% choline - - -... Aloc-LeuPro-OH - - - - - - - - - . LeuProCys(Far)OMe esterase, 2. 5 morpholine, 88 % 3 5 96% 1. Me3N, acetone, 97 % 2. HBr/AcOH, thioanisole, 99 % Boc-MetGly-OEtBr ' Aloc-Cys(Pal)MetGly-OCho 3. 5 dirnethyl-Bcyclodextrin 76% DMAP, 88% 7 EDC, HOBt, HLeuProCys(Far)OMe (5) • Aloc-Cys(Pal)MeIGly-OH - - - - - - - - - . 97% 8 Aloc-CysMetGlyLeuProCys-OMe os) 9 ~\ Scheme 4. N-Ras synthesis employing the choline ester as C-terminal protecting group; EEDQ: 2ethoxy-N-ethoxycarbonyl-l,2-dihydroquinoline, DMAP: dimethylam inopyridine, EDC: l-ethyl-3(dimethylamino)-propylcarbodiimide hydrochloride , HOBt: l-hydroxybenzotriazole From the palmitoylated base-labile tripeptide 7, the choline ester was removed selectively and in high yield by means of the enzyme in the presence of dimethyl,B-cyclodextrin.

The enantiomeric preference of CaLB in the aminolysis of a-substituted acyl donors is summarized in Fig. 12. The preferentially formed enantiomers of 1 [62], ibuprofen amides (2) [19,29,30], phenylglycine amide (3) [64], and derivatives of glutamic acid (4) [37] seem to correspond with a common steric model with the substituents arranged as indicated in Fig. 12. Only the selective (E = 25) formation of (S)-N-pentylpyroglutamic amide (5) [66] does not easily fit into the pattern. 34 F. van Rantwijk et al.

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