2004
DOI: 10.1002/anie.200353338
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Coupling of Biocatalytic Asymmetric Epoxidation with NADH Regeneration in Organic–Aqueous Emulsions

Abstract: Cell‐free enzymatic oxidations: Styrene monooxygenase (StyA) was used as a reagent for the gram‐scale preparation of enantiopure epoxides. The catalyst is highly stable in a biphasic system and results in conversions of more than 88 %. R1=H, Cl; R2=R3=H, CH3.

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Cited by 92 publications
(69 citation statements)
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“…[54] While volumetric productivities reported here are quite low (maximum 0.15 g l -1 h -1 ), higher values found in literature (up to 1 g l -1 h -1 ) [8] are usually calculated for reaction times of 10 h or less compared to up to 100 h in our P450-mediated approach.Switching the cofactor specificity of CYP102A1 to NADH allows to reduce the cofactor costs to about 20%. Further investigations concerning the stability and general applicability of the NAD + -dependent reaction system are required.…”
Section: Discussioncontrasting
confidence: 51%
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“…[54] While volumetric productivities reported here are quite low (maximum 0.15 g l -1 h -1 ), higher values found in literature (up to 1 g l -1 h -1 ) [8] are usually calculated for reaction times of 10 h or less compared to up to 100 h in our P450-mediated approach.Switching the cofactor specificity of CYP102A1 to NADH allows to reduce the cofactor costs to about 20%. Further investigations concerning the stability and general applicability of the NAD + -dependent reaction system are required.…”
Section: Discussioncontrasting
confidence: 51%
“…The total turnover numbers for the biocatalyst exceed the value of up to 2867 reported for the asymmetric epoxidation of styrene by styrene monooxygenase (StyAB) in a two-phase dodecane / aqueous buffer system. [8] In this case for the cofactor NAD + a maximum turnover number of 87 was detrmined. Lutz et al investigated the preparative application of 2-hydroxybiphenyl 3-monooxygenase with enzymatic cofactor regeneration.…”
Section: Discussionmentioning
confidence: 95%
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“…Yet, only a few such processes have been scaled to production level, since biotransformation rates typically are rather unstable and activities during long-term biotransformations are often lower than maximal activities obtained in short-term assays with whole cells (6,10,48,54), cell extracts (13), and enriched enzyme preparations (26). The physiology of whole-cell redox biocatalysts during long-term biotransformations is largely unknown, although it is influenced by biocatalysis and may at least in part be responsible for limited biocatalyst activities and stabilities.…”
Section: Discussionmentioning
confidence: 99%