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- W59067568 abstract "The kinetic resolution of a chiral ester by enzyme catalysed hydrolysis is a well-known process and is illustrated by the preparation of a synthon for the natural product coriolic acid. The stereoselective hydrolysis of meso-diesters can give rise to useful optically active intermediates e.g. for the synthesis of carbocyclic ribonucleosides. The enantioselective esterification of a bicyclic secondary alcohol has been used to give access to homochiral prostaglandin precursors. Acylases have been employed to hydrolyse a γ-lactam in enantiospecific fashion and the optically active materials obtained have been converted into the anti-HIV agent carbovir and into an unnatural amino-acid which binds to the GABA receptor. The natural β-amino-acid cispentacin has been prepared by a similar strategy. The less well-developed areas involving enzyme-catalysed hydrolysis of phosphate esters, epoxides and nitriles are also discussed. Reduction of substituted bicyclo[3.2.0]heptanones by dehydrogenase enzymes (either as isolated enzymes or within whole cell systems) gives rise to useful materials for the construction of the pheromone eldanolide and the chemokinetic agent leukotriene B4. Oxidation of benzene and derivatives by dioxygenase enzymes furnishes substituted cyclohexadienediols that can be modified by employing [4+2] and [2+2] cycloaddition reactions. The utility of the enzymic Baeyer Villiger reaction is exemplified by its use in the preparation of δ-lactones that can be converted into anti-HIV agents. Soybean lipoxygenase is useful for the synthesis of 13-HODE and analogues while the opportunities offered by organisms such as Beauveria sulfurescens, that are capable of oxidising organic substrates at ostensibly non-activated positions, are noted. Enzymes that catalyse formation of carbon-carbon bonds are of importance. The uses of rabbit muscle aldolase to form trioses and lyases to form cyanohydrins provide good examples. Amongst future developments in the field of biotransformations, the use of more than one enzyme in the same reaction vessel in order to catalyse a cascade of sequential reactions is a particularly attractive proposition." @default.
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- W59067568 date "1992-01-01" @default.
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- W59067568 title "Use of Enzymes as Catalysts in Key Reactions Leading to the Synthesis of Optically Active Natural Products and Analogues" @default.
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- W59067568 doi "https://doi.org/10.1007/978-94-011-2444-7_8" @default.
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