Microbial Reagents in Organic Synthesis

Different aspects of biocatalysis are discussed with a view to obtaining products in a practical way using microorganisms and enzymes in catalytic amounts but as if they were organic reagents. A limited number of reactions catalysed by microbial reagents have been examinded according to the following classes: C-C bond formation, including the reaction catalyzed by aldolases, enantiomeric oxynitrilases, and decarboxylases. Oxidations promoted by microorganisms leading to Bayer-Williger-type products and hydroxylation at saturated carbon also includes the production of synthons derived from the microbial oxidation of substituted aromatics of wide synthetic applications. Reductions of carbonyl group with yeasts and other microorganisms, including the factor affecting the stereoselectivity when using all-cell organisms. Group transfer reactions describes synthetic achievements and theoretical aspects concerning the use of lipases, esterases and acylases. Industrial applications of microbial reagents in the large-scale production of fine chemicals offers validation to the basic research in the field.

Zusammenfassung
Proceedings of the NATO Advanced Research Workshop, Sestri Levante, Italy, March 23-27, 1992

Inhalt
C-C Bond Formation.- Cyclase mediated synthesis of terpenoids.- (R)- and (S)-Cyanohydrins Their enzymatic synthesis and their reactions.- Chemical-enzymatic synthesis of carbohydrates.- A building block strategy for asymmetric synthesis: the DHAP-aldolases.- Transferase catalyzed synthesis: applications in series of aminoacids and monosaccharides.- Acyloin formation mediated by benzoylformate decarboxylases.- Synthetic Applications.- Organic synthesis via biocatalytic methods A chemoenzymatic approach to the synthesis of FK506.- Use of enzymes as catalysts in key reactions leading to the synthesis of optically active natural products and analogues.- New enzymatic methods for the selective functionalization of carbohydrate derivatives.- Efficient synthesis of optically active carbohydrates and other oxygenated compounds through bio-oxidation of chlorinated aromatics.- Chemoenzymatic synthesis of natural products and bioactive compounds.- Biotransformations applied to the synthesis of vitamins and pharmaceuticals.- Hydrolytic and Proteolytic Enzymes.- A direct route from hydantoins to D-amino acids employing a resting cell biocatalyst with D-hydantoinase and D-carbamoylase activity.- The use of immobilized penicillin G acylase in organic synthesis.- Are proteases suitable tools for the formation of peptide bonds?.- Enzymatic aminolysis, hydrazinolysis and oximolysis reactions.- Microbial and enzymatic transformation of nitriles.- Resolution of racemates with lipases and effect of reaction conditions on enantioselectivity.- Selectivity enhancement of Candida cylindracea lipase: covalent enzyme modification and control of micro-pH.- Lipase catalyzed organic synthesis.- Kinetics and validation of mathematical models of enantioselective transesterification in organicsolvents.- Enzymatic enantioselective ester hydrolysis by carboxylesterase NP.- A kinetic interpretation of acids and alcohols influence on the enantioselectivity in enzyme catalysed resolutions.- Asymmetrized tris(hydroxymethyl)methane and related synthons as new highly versatile chiral building blocks. Chemoenzymatic preparation and synthetic applications.- Oxidations.- A comparative study of chemical versus biological functionalizations of synthetic intermediates.- Enantioselective sulfoxidations catalyzed by chloroperoxidase and horseradish peroxidase.- Use of biooxygenation in fine organic synthesis.- The enzymatic Baeyer-Villiger oxidation.- Beauveria Sulfurescens mediated oxidation of dihydroartemisin derivates.- Reductions.- Comparison of chemical and biochemical reduction methods for the synthesis of (R)-2-hydroxy-4-phenylbutyric acid.- Stereochemical control in microbial reduction.- Approaches to 2-methyl-l-alkanols of high enantiomeric purities via enzyme mediated reactions.- Microbial alcohol/aldehyde oxidoreductases in enantioselective conversions.- Stereocontrolled reduction of ?-ketoesters with Geotriehum candidum.- Usefull enzymes from plant cell and organ cultures.- List of Contributors.- List of Participants.