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Literature summary for 4.2.3.146 extracted from

  • Meguro, A.; Motoyoshi, Y.; Teramoto, K.; Ueda, S.; Totsuka, Y.; Ando, Y.; Tomita, T.; Kim, S.Y.; Kimura, T.; Igarashi, M.; Sawa, R.; Shinada, T.; Nishiyama, M.; Kuzuyama, T.
    An unusual terpene cyclization mechanism involving a carbon-carbon bond rearrangement (2015), Angew. Chem. Int. Ed. Engl., 54, 4353-4356 .
    View publication on PubMed
Search for more literature for 4.2.3.146

Protein Variants

Protein Variants Comment Organism
F107A site-directed mutagenesis, the mutant follows a different reaction mechanism compared to wild-type and produces the different product cembrane A in addition to cyclooctat-9-en-7-ol Streptomyces melanosporofaciens
F107Y site-directed mutagenesis, the mutant follows a different reaction mechanism compared to wild-type and produces the different product cyclooctat-1,7-diene Streptomyces melanosporofaciens
F149L site-directed mutagenesis, the mutant follows a different reaction mechanism compared to wild-type and produces the different product cyclooctat-7-en-3-ol, no formation of cyclooctat-9-en-7-ol Streptomyces melanosporofaciens
W288G site-directed mutagenesis, the mutant follows a different reaction mechanism compared to wild-type and produces the different product 3,7,18-dolabellatriene 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
-
-

Reaction

Reaction Comment Organism Reaction ID
geranylgeranyl diphosphate + H2O = cyclooctat-9-en-7-ol + diphosphate cyclization reaction mechanism analysis using three regiospecifically deuterated samples of geranylgeranyl diphosphate, the reaction proceeds via several cationic intermediates, detailed overview. Enzyme CotB2 catalyzes an unusually complex regiospecific and stereospecific cyclization that involves a unique carbon-carbon bond rearrangement and multiple hydride shifts, which all take place at a single active site Streptomyces melanosporofaciens
a

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
-
 ?
additional information CotB2 has the unique ability to synthesize the characteristic 5-8-5 fused-ring system of cyclooctat-9-en-7-ol having six chiral centers by cyclization of the universal diterpene precursor, the achiral C20 allylic diphosphate GGDP Streptomyces melanosporofaciens ?
-
 ?
additional information CotB2 has the unique ability to synthesize the characteristic 5-8-5 fused-ring system of cyclooctat-9-en-7-ol having six chiral centers by cyclization of the universal diterpene precursor, the achiral C20 allylic diphosphate GGDP Streptomyces melanosporofaciens MI614-43F2 ?
-
 ?

Synonyms

Synonyms Comment Organism
CotB2
-
 Streptomyces melanosporofaciens

General Information

General Information Comment Organism
physiological function the enzyme catalyzes the formation of cyclooctat-9-en-7-ol, which is a precursor of cyclooctatin, a diterpene with a unique tricyclic diterpene skeleton characterized by a 5-8-5 fused-ring system, which is a potent inhibitor of lysophospholipase, an enzyme that catalyzes the hydrolysis of the fatty acid ester bonds of lysophospholipids Streptomyces melanosporofaciens