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Literature summary extracted from

  • Toda, H.; Ohuchi, T.; Imae, R.; Itoh, N.
    Microbial production of aliphatic (S)-epoxyalkanes by using Rhodococcus sp. strain ST-10 styrene monooxygenase expressed in organic-solvent-tolerant Kocuria rhizophila DC2201 (2015), Appl. Environ. Microbiol., 81, 1919-1925 .
    View publication on PubMedView publication on EuropePMC

Application

EC Number Application Comment Organism
1.14.14.11 synthesis in an organic solvent-water biphasic reaction system, recombinant enzyme enantioselectively converts linear terminal alkenes to their corresponding (S)-epoxyalkanes using glucose and molecular oxygen. When 1-heptene and 6-chloro-1-hexene are used as substrates (400 mM) under optimized conditions, 88.3mM (S)-1,2-epoxyheptane and 246.5mM (S)-1,2-epoxy-6-chlorohexane, respectively, accumulate in the organic phase with good enantiomeric excess (84.2% and 95.5%, respectively) Rhodococcus sp. ST-10

Cloned(Commentary)

EC Number Cloned (Comment) Organism
1.14.14.11 expression in Kocuria rhizophila DC2201 Rhodococcus sp. ST-10

Organic Solvent Stability

EC Number Organic Solvent Comment Organism
1.14.14.11 additional information for epoxyalkane production in a biophasic system, di-n-octyl phthalate and bis(2-ethylhexyl)phthalate are the best solvents. Phthalate esters, except methyl phthalate, produce higher levels of (S)-1,2-epoxyheptane than medium- or long-chain (C10 to C18) alkanes Rhodococcus sp. ST-10

Organism

EC Number Organism UniProt Comment Textmining
1.14.14.11 Rhodococcus sp. ST-10 G3XEX2
-
-

Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
1.14.14.11 2-methylhex-1-ene + FADH2 + O2
-
 Rhodococcus sp. ST-10 (S)-1,2-epoxy-2-methylhexane + FAD + H2O
-
 ?
1.14.14.11 6-bromohex-1-ene + FADH2 + O2
-
 Rhodococcus sp. ST-10 (S)-1,2-epoxy-6-bromohexane + FAD + H2O
-
 ?
1.14.14.11 6-chlorohex-1-ene + FADH2 + O2
-
 Rhodococcus sp. ST-10 (S)-1,2-epoxy-6-chlorohexane + FAD + H2O
-
 ?
1.14.14.11 hept-1-ene + FADH2 + O2
-
 Rhodococcus sp. ST-10 (S)-1,2-epoxy-2-methylhexane + FAD + H2O
-
 ?
1.14.14.11 additional information upon reaction in an organic solvent-water biphasic reaction system, the highest production level (246.5 mM) is achieved for 6-chloro-1-hexene, followed by styrene, 6-bromo-1-hexene, 2-methyl-1-hexene, 1-heptene, and 5-hexenenitrile in decreasing order Rhodococcus sp. ST-10 ?
-
 ?
1.14.14.11 styrene + FADH2 + O2
-
 Rhodococcus sp. ST-10 (S)-styrene oxide + FAD + H2O
-
 ?

Synonyms

EC Number Synonyms Comment Organism
1.14.14.11 StyA
-
 Rhodococcus sp. ST-10