Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
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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:
pentalenene synthase Inferred from experiment : ptlA ( Streptomyces avermitilis )
pentalenene synthase Inferred from experiment : ptlA ( Streptomyces exfoliatus )

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 Enzyme Commission system.

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: ?

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
Page generated by SRI International Pathway Tools version 18.5 on Sat Nov 22, 2014, BIOCYC13A.