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Literature summary for 4.2.3.203 extracted from

  • Zev, S.; Ringel, M.; Driller, R.; Loll, B.; Brueck, T.; Major, D.T.
    Understanding the competing pathways leading to hydropyrene and isoelisabethatriene (2022), Beilstein J. Org. Chem., 18, 972-978.
    View publication on PubMed
Search for more literature for 4.2.3.203

Protein Variants

Protein Variants Comment Organism
M75L mutation diverts the product distribution towards isoelisabethatrienes A and B Antillogorgia elisabethae

Organism

Organism UniProt Comment Textmining
Antillogorgia elisabethae
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-
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Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
geranylgeranyl diphosphate
-
 Antillogorgia elisabethae hydropyrene + hydropyrenol + isoelisabethatriene A + isoelisabethatriene B + diphosphate
-
 ?

General Information

General Information Comment Organism
metabolism in wild-type, there is a great thermodynamic preference for hydropyrene and hydropyrenol formation. The synthesis of the isoelisabethatriene byproducts is under kinetic control. to IEs A and B as well as hydropyrene and hydropyrenol. In the reactions generating isoelisabethatrienes there is an exchange of two pi-bonds for sigma-bonds, resulting in a total exergonicity of -34.4 and -35.9 kcal/mol, respectively. The reactions to hydropyrene and hydropyrol replace four pi-bonds for sigma-bonds and share a common final carbocation, the exergonicity is -62.8 kcal/mol. These values reflect the energetics of exchanging pi-bonds for sigma-bonds Antillogorgia elisabethae