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MetaCyc Reaction: 4.2.3.7

Superclasses: Reactions Classified By Conversion Type Simple Reactions Chemical Reactions
Reactions Classified By Substrate Small-Molecule Reactions

EC Number: 4.2.3.7

Enzymes and Genes:

Streptomyces avermitilis : pentalenene synthase Inferred from experiment : ptlA
Streptomyces exfoliatus : pentalenene synthase Inferred from experiment : ptlA

In Pathway: pentalenolactone biosynthesis , neopentalenoketolactone and pentalenate biosynthesis

Supersedes EC number: 4.6.1.5

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 Inferred by computational analysis [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.

Citations: [Lesburg97, Cane91, Cane84, Cane83, Zu12]

Gene-Reaction Schematic: ?

Gene-Reaction Schematic

Unification Links: KEGG:R02305 , Rhea:18081

Relationship Links: BRENDA:EC:4.2.3.7 , ENZYME:EC:4.2.3.7 , IUBMB-ExplorEnz:EC:4.2.3.7


References

Cane83: Cane DE (1983). "Cell-free studies of monoterpene and sesquiterpene biosynthesis." Biochem Soc Trans 11(5);510-5. PMID: 6642060

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

Latendresse13: Latendresse M. (2013). "Computing Gibbs Free Energy of Compounds and Reactions in MetaCyc."

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


Report Errors or Provide Feedback
Please cite the following article in publications resulting from the use of MetaCyc: Caspi et al, Nucleic Acids Research 42:D459-D471 2014
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