Abstract
Enantioselective synthesis of some important antibiotics has been investigated by combination of enzymatic and non-enzymatic procedures. The synthetic strategy developed here is based on symmetri-zatlon-asymmetrization concept. Thus, retrosynthesls was carried out to generate, from target molecules, simplified symmetric diesters (symmetrization), and then the symmetric diesters were subjected to asymmetric hydrolysis with pig liver esterase to create the corresponding chiral half-esters. The chiral half-esters were converted to the target molecules by non-enzymatic procedures. Various types of carbapenem antibiotics, negamycin, showdomycin, 6-azapseudouridine, cordycepin, aristeromycin, neplanocin A, and aminocyclitol of fortimicin were efficiently synthesized with the desired absolute configurations. The structure-stereospecificty relationships revealed by the present study give significant and useful information about the topography of the active site of PLE and allow us to propose the working active site model.
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© 1986 D. Reidel Publishing Company
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Ohno, M., Kobayashi, S., Adachi, K. (1986). Creation of Novel Chiral Synthons with Pig Liver Esterase: Application to Natural Product Synthesis and the Substrate Recognition. In: Schneider, M.P. (eds) Enzymes as Catalysts in Organic Synthesis. NATO ASI Series, vol 178. Springer, Dordrecht. https://doi.org/10.1007/978-94-009-4686-6_8
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DOI: https://doi.org/10.1007/978-94-009-4686-6_8
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