42 豚肝臓エステラーゼ(PLE)によるキラルシントンの創製とその天然物合成への応用及びその基質認識

概要

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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 symmetrization-asymmetrization concept. Thus, retrosyntesis 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 precursors of fortimicin were efficiently synthesized with the desired absolute configurations. The structure-stereospecificity 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.
天然有機化合物討論会の論文
1985-09-07