Abstract:The last few decades have seen a steady increase in the global production and utilisation of the alkenylbenzene, styrene. The compound is of major importance in the petrochemical and polymer-processing industries, which can contribute to the pollution of natural resources via the release of styrene-contaminated effluents and off-gases. This is a cause for some concern as human over-exposure to styrene, and/or its early catabolic intermediates, can have a range of destructive health effects. These features have… Show more
“…Phenylacetaldehyde and phenylacetic acid have been found to be intermediates of the microbiological styrene degradation via side-chain oxidation [31]. This degradation route has been reported for several bacteria, e.g., representatives of the genus Pseudomonas
[25], [30], [36], [45], Rhodococcus
[32], [35], [44], or Sphingopyxis
[35].…”
Section: Introductionmentioning
confidence: 92%
“…In order to establish a biotechnological process for the synthesis of phenylacetaldehyde, previous investigations were performed with styrene oxide isomerases (SOI, encoded by styC ). These enzymes are involved in the microbiological styrene degradation and convert styrene oxide into phenylacetaldehyde [16], [19], [27], [31], [32]. Despite of the high SOI activities in some wild-type strains [35] the production of SOIs by these strains is very time-consuming [34].…”
“…Phenylacetaldehyde and phenylacetic acid have been found to be intermediates of the microbiological styrene degradation via side-chain oxidation [31]. This degradation route has been reported for several bacteria, e.g., representatives of the genus Pseudomonas
[25], [30], [36], [45], Rhodococcus
[32], [35], [44], or Sphingopyxis
[35].…”
Section: Introductionmentioning
confidence: 92%
“…In order to establish a biotechnological process for the synthesis of phenylacetaldehyde, previous investigations were performed with styrene oxide isomerases (SOI, encoded by styC ). These enzymes are involved in the microbiological styrene degradation and convert styrene oxide into phenylacetaldehyde [16], [19], [27], [31], [32]. Despite of the high SOI activities in some wild-type strains [35] the production of SOIs by these strains is very time-consuming [34].…”
“…These styrenes are partly available in large amounts from the polymer industry [23] and can be converted by soil bacteria harboring enzymes of the styrene-catabolic pathway of side-chain oxygenation [32], [36]. During side-chain oxygenation, the substrate styrene is initially oxidized into styrene oxide by styrene monooxygenase (SMO, EC 1.14.14.11, encoded by styA / styB ) and subsequently transformed into phenylacetaldehyde by styrene oxide isomerase (SOI, EC 5.3.99.7, encoded by styC ) (see Fig.…”
Section: Introductionmentioning
confidence: 99%
“…Previous studies have elucidated enzymes involved in the side-chain oxygenation of styrene in, for example, representatives of the genera Corynebacterium , Rhodococcus , Pseudomonas , Sphingopyxis , or Xanthobacter
[5], [20], [22], [33], [34], [35], [47].…”
Section: Introductionmentioning
confidence: 99%
“…Styrene (R1, R2 = H) is transformed to phenylacetic acid through enzymes of side-chain oxygenation by the following steps: (a) initial epoxidation to styrene oxide by styrene monooxygenase (SMO), (b) isomerization to phenylacetaldehyde by styrene oxide isomerase (SOI), (c) oxidation by phenylacetaldehyde dehydrogenase (PAD) (reviewed by [32], [36]). A star indicates the formation of a stereocenter in case of R1 = CH 3 .…”
Monooxygenases perform chemo-, regioand/or enantioselective oxygenations of organic substrates under mild reaction conditions. These properties and the increasing number of representatives along with effective preparation methods place monooxygenases in the focus of industrial biocatalysis. Mechanistic and structural insights reveal reaction sequences and allow turning them into efficient tools for the production of valuable products. Herein we describe two biocatalytically relevant subclasses of flavoprotein monooxygenases with a close evolutionary relation: subclass A represented by p-hydroxybenzoate hydroxylase (PHBH) and subclass E formed by styrene monooxygenases (SMOs). PHBH family members perform highly regioselective hydroxylations on a wide variety of aromatic compounds. The more recently discovered SMOs catalyze a number of stereoselective epoxidation and sulfoxidation reactions. Mechanistic and structural studies expose distinct characteristics, which provide a promising source for future biocatalyst development.
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