The Enzyme Database

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EC 1.14.13.133      
Transferred entry: pentalenene oxygenase. Now EC 1.14.15.32, pentalenene oxygenase
[EC 1.14.13.133 created 2011, deleted 2018]
 
 
EC 1.14.15.32     
Accepted name: pentalenene oxygenase
Reaction: pentalenene + 4 reduced ferredoxin [iron-sulfur] cluster + 4 H+ + 2 O2 = pentalen-13-al + 4 oxidized ferredoxin [iron-sulfur] cluster + 3 H2O (overall reaction)
(1a) pentalenene + 2 reduced ferredoxin [iron-sulfur] cluster + 2 H+ + O2 = pentalen-13-ol + 2 oxidized ferredoxin [iron-sulfur] cluster + H2O
(1b) pentalen-13-ol + 2 reduced ferredoxin [iron-sulfur] cluster + 2 H+ + O2 = pentalen-13-al + 2 oxidized ferredoxin [iron-sulfur] cluster + 2 H2O
For diagram of humulene-based sequiterpenoid biosynthesis, click here
Other name(s): PtlI
Systematic name: pentalenene,reduced ferredoxin:oxygen 13-oxidoreductase
Comments: A cytochrome P-450 (heme-thiolate) protein found in the bacterium Streptomyces avermitilis. The enzyme is involved in the biosynthesis of pentalenolactone and related antibiotics.
Links to other databases: BRENDA, EXPASY, KEGG, MetaCyc
References:
1.  Quaderer, R., Omura, S., Ikeda, H. and Cane, D.E. Pentalenolactone biosynthesis. Molecular cloning and assignment of biochemical function to PtlI, a cytochrome P450 of Streptomyces avermitilis. J. Am. Chem. Soc. 128 (2006) 13036–13037. [DOI] [PMID: 17017767]
[EC 1.14.15.32 created 2011 as EC 1.14.13.133, transferred 2018 to EC 1.14.15.32]
 
 
EC 4.2.3.7     
Accepted name: pentalenene synthase
Reaction: (2E,6E)-farnesyl diphosphate = pentalenene + diphosphate
For diagram of sesquiterpenoid biosynthesis based on humulene, click here
Glossary: pentalenene = (1R,8aR)-1,4,7,7-tetramethyl-1,2,3,3a,5a,6,7,8-octahydrocyclopenta[c]pentalene
Other name(s): pentalenene synthetase
Systematic name: (2E,6E)-farnesyl-diphosphate diphosphate-lyase (cyclizing, pentalenene-forming)
Comments: 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.
Links to other databases: BRENDA, EXPASY, KEGG, MetaCyc, PDB, CAS registry number: 90597-46-9
References:
1.  Cane, D.E. Cell-free studies of monoterpene and sesquiterpene biosynthesis. Biochem. Soc. Trans. 11 (1983) 510–515. [PMID: 6642060]
2.  Cane, D.E. and Tillman, A.M. Pentalenene biosynthesis and the enzymic cyclization of farnesyl pyrophosphate. J. Am. Chem. Soc. 105 (1983) 122–124.
3.  Cane, D.E., Sohng, J.K., Lamberson, C.R., Rudnicki, S.M., Wu, Z., Lloyd, M.D., Oliver, J.S. and Hubbard, B.R. Pentalenene synthase. Purification, molecular cloning, sequencing, and high-level expression in Escherichia coli of a terpenoid cyclase from Streptomyces UC5319. Biochemistry 33 (1994) 5846–5857. [PMID: 8180213]
4.  Cane, D.E., Abell, C., Harrison, P.H., Hubbard, B.R., Kane, C.T., Lattman, R., Oliver, J.S. and Weiner, S.W. Terpenoid biosynthesis and the stereochemistry of enzyme-catalysed allylic addition-elimination reactions. Philos. Trans. R. Soc. Lond. B Biol. Sci. 332 (1991) 123–129. [DOI] [PMID: 1678531]
5.  Lesburg, C.A., Zhai, G., Cane, D.E. and Christianson, D.W. Crystal structure of pentalenene synthase: mechanistic insights on terpenoid cyclization reactions in biology. Science 277 (1997) 1820–1824. [DOI] [PMID: 9295272]
6.  Zu, L., Xu, M., Lodewyk, M.W., Cane, D.E., Peters, R.J. and Tantillo, D.J. Effect of isotopically sensitive branching on product distribution for pentalenene synthase: support for a mechanism predicted by quantum chemistry. J. Am. Chem. Soc. 134 (2012) 11369–11371. [DOI] [PMID: 22738258]
[EC 4.2.3.7 created 1989 as EC 4.6.1.5, transferred 2000 to EC 4.2.3.7]
 
 
EC 4.2.3.160     
Accepted name: (2S,3R,6S,9S)-(–)-protoillud-7-ene synthase
Reaction: (2E,6E)-farnesyl diphosphate = (2S,3R,6S,9S)-(–)-protoillud-7-ene + diphosphate
For diagram of bicyclic and tricyclic sesquiterpenoids derived from humuladienyl cation, click here and for diagram of protoilludene and related sesquiterpenoids, click here
Glossary: (2S,3R,6S,9S)-(–)-protoillud-7-ene = (2aS,4aS,7aS,7bR)-3,6,6,7b-tetramethyl-2,2a,4a,5,6,7,7a,7b-octahydro-1H-cyclobuta[e]indene
pentalenene = (3aS,5aS,8aR)-1,4,7,7-tetramethyl-1,2,3,3a,5a,6,7,8-octahydrocyclopenta[c]pentalene
Other name(s): TPS6 (gene name)
Systematic name: (2E,6E)-farnesyl-diphosphate diphosphate-lyase [cyclizing, (2S,3R,6S,9S)-(–)-protoillud-7-ene-forming]
Comments: The enzyme has been described from the slime-mould Dictyostelium discoideum. It is specific for (2E,6E)-farnesyl diphosphate. While the major product is the sequiterpene (2S,3R,6S,9S)-(–)-protoillud-7-ene, traces of pentalenene are also formed.
Links to other databases: BRENDA, EXPASY, KEGG, MetaCyc
References:
1.  Chen, X., Kollner, T.G., Jia, Q., Norris, A., Santhanam, B., Rabe, P., Dickschat, J.S., Shaulsky, G., Gershenzon, J. and Chen, F. Terpene synthase genes in eukaryotes beyond plants and fungi: occurrence in social amoebae. Proc. Natl. Acad. Sci. USA 113 (2016) 12132–12137. [DOI] [PMID: 27790999]
2.  Rabe, P., Rinkel, J., Nubbemeyer, B., Kollner, T.G., Chen, F. and Dickschat, J.S. Terpene cyclases from social Amoebae. Angew. Chem. Int. Ed. Engl. 55 (2016) 15420–15423. [DOI] [PMID: 27862766]
[EC 4.2.3.160 created 2017]
 
 
EC 4.6.1.5      
Transferred entry: pentalenene synthase. Now EC 4.2.3.7, pentalenene synthase
[EC 4.6.1.5 created 1989, deleted 2000]
 
 


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