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Biosci Biotechnol Biochem ; 84(7): 1339-1344, 2020 Jul.
Article in English | MEDLINE | ID: mdl-32290758

ABSTRACT

Catathelasmols C, D, and E, which had been isolated from Catathelasma imperiale as inhibitors for 11-hydroxysteroid dehydrogenases, were comprehensively semisynthesized from commercially available D-glutamic acid. The key synthetic intermediate, (R)-pentane-1,2,5-triol, was site-selectively acetylated by treatment with vinyl acetate and Candida antarctica lipase B (Novozym 435) in tetrahydrofuran (THF) at 25°C to furnish 1,5-diacetate (catathelasmol E, quantitative). The acetylation occurred site-selectively on the primary alcohols at the C-1 and C-5 positions over the secondary alcohol at the C-2 position. Dichromic acid oxidation provided 2-oxopentane-1,5-diyl diacetate (catathelasmol C, 78%). Burkholderia cepacia lipase-catalyzed transesterification with methanol in THF at - 5°C proceeded preferentially on the acetate at C-1 located adjacent to the C-2 carbonyl group over the other terminal acetate at the C-5 position. 5-Hydroxy-4-oxopentyl acetate (catathelasmol D) was obtained in 53% yield.


Subject(s)
11-beta-Hydroxysteroid Dehydrogenases/antagonists & inhibitors , Agaricales/chemistry , Catalytic Domain , Glutamic Acid/metabolism , Lipase/metabolism , Pentanols/chemical synthesis , Acetates/metabolism , Acetylation , Burkholderia cepacia/enzymology , Catalysis , Fungal Proteins/metabolism , Furans/metabolism , Methanol/metabolism , Pentanols/isolation & purification , Secondary Metabolism
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