154804-11-2Relevant academic research and scientific papers
Enantiocomplementary Epoxidation Reactions Catalyzed by an Engineered Cofactor-Independent Non-natural Peroxygenase
Crotti, Michele,Kataja, Kim M.,Poelarends, Gerrit J.,Saravanan, Thangavelu,Xu, Guangcai
, p. 10374 - 10378 (2020)
Peroxygenases are heme-dependent enzymes that use peroxide-borne oxygen to catalyze a wide range of oxyfunctionalization reactions. Herein, we report the engineering of an unusual cofactor-independent peroxygenase based on a promiscuous tautomerase that accepts different hydroperoxides (t-BuOOH and H2O2) to accomplish enantiocomplementary epoxidations of various α,β-unsaturated aldehydes (citral and substituted cinnamaldehydes), providing access to both enantiomers of the corresponding α,β-epoxy-aldehydes. High conversions (up to 98 %), high enantioselectivity (up to 98 % ee), and good product yields (50–80 %) were achieved. The reactions likely proceed via a reactive enzyme-bound iminium ion intermediate, allowing tweaking of the enzyme's activity and selectivity by protein engineering. Our results underscore the potential of catalytic promiscuity for the engineering of new cofactor-independent oxidative enzymes.
A NOVEL SYNTHESIS OF 2,3-EPOXY-3-ARYLPROPANOL VIA ARSONIUM SALT
Shi, Lilian,Wang, Weibo,Huang, Yao-Zeng
, p. 5295 - 5296 (2007/10/02)
In the presence of KOH(s), β-hydroxyethyltriphenylarsonium bromide 2 reacted directly with aromatic aldehydes at r.t. to give 2,3-epoxy-3-arylpropanol 3 in good yields under solid-liquid phase transfer condition.
