- Bioproduction of chiral epoxyalkanes using styrene monooxygenase from rhodococcus sp. ST-10 (RhSMO)
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We describe the enantioselective epoxidation of straight-chain aliphatic alkenes using a biocatalytic system containing styrene monooxygenase from Rhodococcus sp. ST-10 and alcohol dehydrogenase from Leifsonia sp. S749. The biocatalyzed enantiomeric epoxidation of 1-hexene to (S)-1,2-epoxyhexane (44.6 mM) using 2-propanol as the hydrogen donor was achieved under optimized conditions. The biocatalyst had broad substrate specificity for various aliphatic alkenes, including terminal, internal, unfunctionalized, and di- and tri-substituted alkenes. Here, we demonstrate that this biocatalytic system is suitable for the efficient production of enantioenriched (S)-epoxyalkanes.
- Toda, Hiroshi,Imae, Ryouta,Itoh, Nobuya
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p. 3443 - 3450
(2015/02/05)
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- Studies towards the synthesis of neopeltolide: Synthesis of a ring-closing metathesis macrocyclization precursor
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An advanced ring-closing metathesis precursor for the synthesis of the marine macrolide neopeltolide is prepared in a stereocontrolled manner by the coupling of the C2-C10 and C11-C16 subunits. The metathesis reaction of 4 with Grubbs' II or Nolan's indenylidene catalyst led to the unexpected formation of cycloheptene 18.
- Florence, Gordon J.,Cadou, Romain F.
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scheme or table
p. 5761 - 5763
(2010/12/18)
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- Asymmetric epoxidation of terminal alkenes with hydrogen peroxide catalyzed by pentafluorophenyl PtII complexes
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Easily accessible chiral PtII complexes 1 allow highly enantioselective and completely regioselective asymmetric epoxidation of terminal alkenes with hydrogen peroxide. Copyright
- Colladon, Marco,Scarso, Alessandro,Sgarbossa, Paolo,Michelin, Rino A.,Strukul, Giorgio
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p. 14006 - 14007
(2007/10/03)
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- Enantioselective epoxidation of terminal alkenes to (R)- and (S)-epoxides by engineered cytochromes P450 BM-3
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Cytochrome P450 BM-3 from Bacillus megaterium was engineered for enantioselective epoxidation of simple terminal alkenes. Screening saturation mutagenesis libraries, in which mutations were introduced in the active site of an engineered P450, followed by recombination of beneficial mutations generated two P450 BM-3 variants that convert a range of terminal alkenes to either (R)- or (S)epoxidc (up to 83 % ee) with high catalytic turnovers (up to 1370) and high epoxidation selectivities (up to 95%). A biocatalytic system using E. coli lysates containing P450 variants as the epoxidation catalysts and in vitro NADPH regeneration by the alcohol dehydrogenase from Thermoanaerobium brockii generates each of the epoxide enantiomers, without additional cofactor.
- Kubo, Takafumi,Peters, Matthew W.,Meinhold, Peter,Arnold, Frances H.
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p. 1216 - 1220
(2007/10/03)
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