Integrated Biocatalytic Synthesis on Gram Scale: The Highly Enantioselective Preparation of Chiral Oxiranes with Styrene Monooxygenase

Schmid, Andreas; Hofstetter, Karin; Feiten, Hans-Jürgen; Hollmann, Frank; Witholt, Bernard

doi:10.1002/1615-4169(200108)343:6/7<732::aid-adsc732>3.0.co;2-q

Cited by 121 publications

(18 citation statements)

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“…SMOs catalyze the transformation of styrene into (S)-styrene oxide in the upper catabolic pathway of styrene degradation [52,53]. Most two-component SMOs are isolated from the genera of Pseudomonas and Rhodococcus and share high sequence similarities [50,51,[54][55][56][57][58]. Besides the two-component SMOs, several self-sufficient one-component SMOs are isolated from Rhodococcus opacus [59][60][61].…”

Section: Introductionmentioning

confidence: 99%

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Biocatalytic Epoxidation for Green Synthesis

Lin

Liu

et al. 2016

Green Biocatalysis

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Section: Introductionmentioning

confidence: 99%

“…Besides the two-component SMOs, several self-sufficient one-component SMOs are isolated from Rhodococcus opacus [59][60][61]. SMOs are competitive enzymes for the synthesis of epoxides, owning to its exquisite regio-and enantioselectivities [54,55,57,62].…”

Section: Introductionmentioning

confidence: 99%

Biocatalytic Epoxidation for Green Synthesis

Lin

Liu

et al. 2016

Green Biocatalysis

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“…Thus, resting cells are preferred as far as the stability of the catalyst is sufficient [118]. In addition, excellent enantioselectivity of >99% ee for the transformation of styrene into (S)-styrene oxide in the presence of a recombinant E. coli expressing sty rene monooxygenase StyAB was obtained in an earlier study [117,119,120].…”

Section: Epoxidation Of Styrenes Forming Epoxidesmentioning

confidence: 99%

Asymmetric Synthesis with Recombinant Whole‐Cell Catalysts

2016

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c h a p t e r 2 3 INTRODUCTIONAsymmetric catalytic transformations play a central role in the field of organic chemistry and are of great interest for applications in the chemical and pharmaceutical industry. Among those, hydrolytic and reverse reactions to form carboxylate deriva tives as well as C─C bond-forming and redox reactions are of particular importance. For a long time this field was dominated by the use of chemocatalysts [1]. For example, numerous chiral heavy-metal complexes have been found to be highly efficient cat alysts, on a technical scale, in particular, for the asymmetric reduction of imines, ketones, and enamides. A representative success story is imine reduction for the man ufacture of metolachlor as one of the largest industrially applied asymmetric chemo catalytic processes to date, and the widely technically applied hydrogenation technology for the reduction of ketones and enamides, for which Noyori and Knowles were awarded the Nobel Prize [2]. An alternative for the production of chiral building blocks, with a continuously increasing number of examples, also on an industrial scale, is biocatalysis. Known for a long time, the use of biocatalytic alternatives has also been limited for a long time, which has been due to-among others-the following two reasons: (i) wild-type whole cells such as baker's yeast require a large amount of biomass (due to the forma tion of the desired enzymes in the cell only in low amounts) and often give unsatisfy ing enantioselectivities (due to the action of more than one enzyme), and (ii) the use of isolated enzymes requires additional costs for cell disruption and enzyme isolation as well as the addition of an external amount of cofactor. Due to impressive progress in the field of molecular biology, these limitations have often been overcome. High overexpression of the desired enzyme in recombinant host organism and high cell density fermentation technology provide efficient and economically attractive access to these microorganisms (so-called designer cells), which contain exclusively the desired biocatalyst (enzyme) in large amounts. Such designer cells can be used directly in organic synthetic reactions without the need to isolate the enzyme in additional downstream operation steps. The presence of the cofactor in the cells requires no addition of an external amount of cofactors or supply thereof in very low amount only. Due to these advantages, recombinant whole cells overexpressing cofactor dependent enzymes have become very attractive catalysts for asymmetric synthesis. This is underlined by an increasing number of recent organic biotransformations based on the use of such "designer cells."

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“…Enantiopure epoxides are valuable intermediates in the synthesis of a number of optically active pharmaceutical compounds (McClay et al 2000;Schmid et al 2001b;Mooney et al 2006). Epoxides have been used for the production of b3-adrenergic receptor agonists, anti-obesity drugs, nematocides and anticancer agents (Lee and Shuler 2007).…”

Section: Biosynthesis Of Epoxidesmentioning

confidence: 99%

“…The asymmetric epoxidation of olefinic compounds and the enantioselective resolution of racemic epoxides using chemocatalysts are a few of the approaches to the chemical synthesis of these important synthons (Lee and Shuler 2007). Styrene monooxygenase (SMO) catalyses the formation of styrene epoxide from styrene (Table 2) (Panke et al 2000;Schmid et al 2001b;O'Leary et al 2002;Otto et al 2004;Mooney et al 2006). This reaction has been used as a model reaction for the development of styrene monooxygenase as a broad range biocatalyst for the synthesis of epoxides.…”

Section: Biosynthesis Of Epoxidesmentioning

confidence: 99%

Dioxygenase- and monooxygenase-catalysed synthesis of cis-dihydrodiols, catechols, epoxides and other oxygenated products

Nolan

O’Connor

2008

Biotechnol Lett

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Oxidoreductases are an emerging class of biotechnologically relevant enzymes due to their regio- and stereo-specificity. The selective oxygenation of aromatic compounds by oxidoreductases has received much attention and a wide range of reactions have been documented using these enzymes from various microbial sources. This review gives an overview of various dioxygenase, monooxygenase and oxidase enzymes that have been manipulated for the synthesis of products such as cis-dihydrodiols, catechols, epoxides and other oxygenated products. The use of protein engineering and its advancement in the synthesis of recombinant enzymes is also discussed.

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Integrated Biocatalytic Synthesis on Gram Scale: The Highly Enantioselective Preparation of Chiral Oxiranes with Styrene Monooxygenase

Cited by 121 publications

References 0 publications

Biocatalytic Epoxidation for Green Synthesis

Biocatalytic Epoxidation for Green Synthesis

Asymmetric Synthesis with Recombinant Whole‐Cell Catalysts

Dioxygenase- and monooxygenase-catalysed synthesis of cis-dihydrodiols, catechols, epoxides and other oxygenated products

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