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Literature summary extracted from

  • Goerner, C.; Hirte, M.; Huber, S.; Schrepfer, P.; Brueck, T.
    Stereoselective chemo-enzymatic oxidation routes for (1R,3E,7E,11S,12S)-3,7,18-dolabellatriene (2015), Front. Microbiol., 6, 1115 .
    View publication on PubMedView publication on EuropePMC

Application

EC Number Application Comment Organism
4.2.3.146 synthesis in vivo CotB2 W288G reconstitution in an Escherichia coli based terpene production system allows efficient production of (1R,3E,7E,11S,12S)-3,7,18-dolabellatriene, which displays antibacterial activity against multi-drug resistant Staphylococcus aureus (MRSA) Streptomyces melanosporofaciens

Cloned(Commentary)

EC Number Cloned (Comment) Organism
4.2.3.146 gene cotB2, recombinant expression of His-tagged wild-type and mutant enzymes in Escherichia coli strain BL21(DE3) Streptomyces melanosporofaciens

Protein Variants

EC Number Protein Variants Comment Organism
4.2.3.146 additional information epoxidation of product (1R,3E,7E,11S,12S)-3,7,18-dolabellatriene from mutant CotB2 W288G by acetic peracid, which is formed in situ by a lipase catalyzed reaction of acetic acid with H2O2, provides efficient access to two monooxidized dolabellanes and to a di-epoxidated dolabellane species. These compounds might act as synthons en-route to other dolabellanes with diversified bioactivities. Almost quantitative 3,7,18-dolabellatriene conversion into the non-natural compound (1R,3E,7E,11S,12S,18R)-dolabella-3,7-diene-20-ol by hydroboration-oxidation with an enantiomeric excess of 94%. Molecular docking of (1R,3E,7E,11S,12S)-3,7,18-dolabellatriene in the P450BM3_F87A and P450BM3_F87A/A328L active site of hydroxylase P450BM3 derived from Bacillus megaterium Streptomyces melanosporofaciens
4.2.3.146 W288G site-directed mutagenesis, the mutant produces (1R,3E,7E,11S,12S)-3,7,18-dolabellatriene instead of the native product cyclooctat-9-en-7-ol. In vivo CotB2 W288G reconstitution in an Escherichia coli based terpene production system, allows efficient production of this olefinic macrocycle Streptomyces melanosporofaciens

Metals/Ions

EC Number Metals/Ions Comment Organism Structure
4.2.3.146 Mg2+ required Streptomyces melanosporofaciens

Natural Substrates/ Products (Substrates)

EC Number Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
4.2.3.146 geranylgeranyl diphosphate + H2O Streptomyces melanosporofaciens
-
cyclooctat-9-en-7-ol + diphosphate
-
?
4.2.3.146 geranylgeranyl diphosphate + H2O Streptomyces melanosporofaciens MI614-43F2
-
cyclooctat-9-en-7-ol + diphosphate
-
?

Organism

EC Number Organism UniProt Comment Textmining
4.2.3.146 Streptomyces melanosporofaciens C9K1X5
-
-
4.2.3.146 Streptomyces melanosporofaciens MI614-43F2 C9K1X5
-
-

Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
4.2.3.146 geranylgeranyl diphosphate + H2O
-
Streptomyces melanosporofaciens cyclooctat-9-en-7-ol + diphosphate
-
?
4.2.3.146 geranylgeranyl diphosphate + H2O
-
Streptomyces melanosporofaciens MI614-43F2 cyclooctat-9-en-7-ol + diphosphate
-
?

Synonyms

EC Number Synonyms Comment Organism
4.2.3.146 CotB2
-
Streptomyces melanosporofaciens