125617-30-3Relevant articles and documents
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 (2020/04/23)
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.
Enantioselective synthesis of (2R,3R)- and (2S,3S)-2-[(3-chlorophenyl)-(2- methoxyphenoxy)methyl]morpholine
Harding, Wayne W.,Hodge, Matthis,Wang, Zhixia,Woolverton, William L.,Parrish, Damon,Deschamps, Jeffrey R.,Prisinzano, Thomas E.
, p. 2249 - 2256 (2007/10/03)
The enantioselective synthesis of the (R,R)- and (S,S)-enantiomers of 1 from commercially available 3-chlorocinnamic acid is reported. The Sharpless asymmetric epoxidation was used to establish the stereocenters in the synthesis of both enantiomers of 1.
Novel phosphonic acid based prodrugs of PMEA and its analogues
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Page 18, (2010/11/30)
Prodrugs of Formula I, their uses, their intermediates, and their method of manufacture are described: 1wherein: M and V are cis to one another and MPO3H2 is a phosphonic acid selected from the group consisting of 9-(2-phosphonylmet