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Literature summary for 4.2.3.146 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

Application Comment Organism
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)

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

Protein Variants

Protein Variants Comment Organism
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
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

Metals/Ions Comment Organism Structure
Mg2+ required Streptomyces melanosporofaciens

Natural Substrates/ Products (Substrates)

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

Organism

Organism UniProt Comment Textmining
Streptomyces melanosporofaciens C9K1X5
-
-
Streptomyces melanosporofaciens MI614-43F2 C9K1X5
-
-

Substrates and Products (Substrate)

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

Synonyms

Synonyms Comment Organism
CotB2
-
Streptomyces melanosporofaciens