Lactones from Unspecific Peroxygenase-Catalyzed In-Chain Hydroxylation of Saturated Fatty Acids

Abstract

γand δ-lactones are valuable flavor and fragrance compounds. Their synthesis depends on the availability of suitable hydroxy fatty acid precursors. Three short unspecific peroxygenases were identified that selectively hydroxylate the C4 and C5 positions of C8−C12 fatty acids to yield after lactonization the corresponding γand δ-lactones. A preference for C4 over C5 hydroxylation gave γ-lactones as the major products. Overoxidation of the hydroxy fatty acids was addressed via the reduction of the resulting oxo acids using an alcohol dehydrogenase in a bienzymatic cascade reaction.

Tetrasulfide bond boosts the anti-tumor efficacy of dimeric prodrug nanoassemblies

“…Besides, γ-thiolactone may be more stable than δ-thiolactone due to the bond angle and ring tension. 44 , 45 This all suggested that γ-thiolactone was more likely to undergo a cyclization reaction, which led to the rapid release of CTX from γ-4S-2CTX. Therefore, γ-4S-2CTX NPs exhibited higher reduction responsiveness than δ-4S-2CTX NPs.…”

Efficient stereoselective synthesis of aryl lactones using engineered ketoreductase ChKRED20 from Chryseobacterium sp. CA49

“…1b). 8 Among them, dehydrogenase (ADH)-catalyzed reduction of γ-keto esters is a straightforward route to prepare enantioenriched lactones. A series of alkyl and aryl lactones have been synthesized through biocatalytic asymmetric reduction.…”