|Superclasses:||Reactions Classified By Conversion Type → Simple Reactions → Chemical Reactions|
|Reactions Classified By Substrate → Small-Molecule Reactions|
EC Number: 18.104.22.168
Enzymes and Genes:
|Streptomyces avermitilis :||pentalenene synthase
|Streptomyces exfoliatus :||pentalenene synthase
Supersedes EC number: 22.214.171.124
The reaction direction shown, that is, A + B ↔ C + D versus C + D ↔ A + B, is in accordance with the direction in which it was curated.
Mass balance status: Balanced.
Enzyme Commission Primary Name: pentalenene synthase
Enzyme Commission Synonyms: pentalenene synθse
Standard Gibbs Free Energy (ΔrG'° in kcal/mol): -70.45999 [Latendresse13]
Enzyme Commission Summary:
Isolated from Streptomyces avermitilis. The enzyme is involved in the biosynthesis of pentalenolactone and related antibiotics. The 9si hydrogen of farnesyl diphosphate undergoes a 1,2-hydride shift where it becomes the 1α hydrogen of pentalenene.
Cane84: Cane DE, Sohng JK, Lamberson CR, Rudnicki SM, Wu Z, Lloyd MD, Oliver JS, Hubbard BR (1984). "Pentalenene synthase. Purification, molecular cloning, sequencing, and high-level expression in Escherichia coli of a terpenoid cyclase from Streptomyces UC5319." Biochemistry 33(19);5846-57. PMID: 8180213
Cane91: Cane DE, Abell C, Harrison PH, Hubbard BR, Kane CT, Lattman R, Oliver JS, Weiner SW (1991). "Terpenoid biosynthesis and the stereochemistry of enzyme-catalysed allylic addition-elimination reactions." Philos Trans R Soc Lond B Biol Sci 332(1263);123-9. PMID: 1678531
Lesburg97: Lesburg CA, Zhai G, Cane DE, Christianson DW (1997). "Crystal structure of pentalenene synthase: mechanistic insights on terpenoid cyclization reactions in biology." Science 277(5333);1820-4. PMID: 9295272
Zu12: Zu L, Xu M, Lodewyk MW, Cane DE, Peters RJ, Tantillo DJ (2012). "Effect of isotopically sensitive branching on product distribution for pentalenene synthase: support for a mechanism predicted by quantum chemistry." J Am Chem Soc 134(28);11369-71. PMID: 22738258
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