The Enzyme Database

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EC 1.14.13.191      
Transferred entry: ent-sandaracopimaradiene 3-hydroxylase. Now EC 1.14.14.70, ent-sandaracopimaradiene 3-hydroxylase
[EC 1.14.13.191 created 2014, deleted 2018]
 
 
EC 1.14.13.192      
Transferred entry: oryzalexin E synthase. Now EC 1.14.14.122, oryzalexin E synthase
[EC 1.14.13.192 created 2014, deleted 2018]
 
 
EC 1.14.13.193      
Transferred entry: oryzalexin D synthase. Now EC 1.14.14.123, oryzalexin D synthase
[EC 1.14.13.193 created 2014, deleted 2018]
 
 
EC 1.14.14.70     
Accepted name: ent-sandaracopimaradiene 3-hydroxylase
Reaction: ent-sandaracopimaradiene + [reduced NADPH—hemoprotein reductase] + O2 = ent-sandaracopimaradien-3β-ol + [oxidized NADPH—hemoprotein reductase] + H2O
For diagram of oryzalexins biosynthesis, click here
Glossary: ent-sandaracopimaradiene = ent-13α-pimara-8(14),15-diene = (4aR,4bR,7S,10aR)-7-ethenyl-1,1,4a,7-tetramethyl-1,2,3,4,4a,4b,5,6,7,9,10,10a-dodecahydrophenanthrene
Other name(s): CYP701A; OsKOL4
Systematic name: ent-sandaracopimaradiene,[reduced NADPH—hemoprotein reductase]:oxygen oxidoreductase (ent-sandaracopimaradien-3β-ol forming)
Comments: A cytochrome P-450 (heme-thiolate) protein isolated from Oryza sativa (rice). Participates in the pathway for the biosynthesis of oryzalexins, a group of related phytoalexins produced by rice. Can also use 9β-pimara-7,15-diene as substrate (cf. EC 1.14.14.68, syn-pimaradiene 3-monooxygenase).
Links to other databases: BRENDA, EXPASY, KEGG, MetaCyc
References:
1.  Wang, Q., Hillwig, M.L., Wu, Y. and Peters, R.J. CYP701A8: a rice ent-kaurene oxidase paralog diverted to more specialized diterpenoid metabolism. Plant Physiol. 158 (2012) 1418–1425. [DOI] [PMID: 22247270]
2.  Wu, Y., Wang, Q., Hillwig, M.L. and Peters, R.J. Picking sides: distinct roles for CYP76M6 and CYP76M8 in rice oryzalexin biosynthesis. Biochem. J. 454 (2013) 209–216. [DOI] [PMID: 23795884]
[EC 1.14.14.70 created 2014 as EC 1.14.13.191, transferred 2018 to EC 1.14.14.70]
 
 
EC 1.14.14.122     
Accepted name: oryzalexin E synthase
Reaction: ent-sandaracopimaradien-3β-ol + [reduced NADPH—hemoprotein reductase] + O2 = oryzalexin E + [oxidized NADPH—hemoprotein reductase] + H2O
For diagram of oryzalexins biosynthesis, click here
Glossary: oryzalexin E = ent-sandaracopimaradiene-3β,9α-diol = (3R,4aR,4bS,7S,10aR)-7-ethenyl-1,1,4a,7-tetramethyl-1,2,3,4,4a,4b,5,6,7,9,10,10a-dodecahydrophenanthren-2,4b-diol
ent-sandaracopimaradien-3β-ol = (3R,4aR,4bR,7S,10aS)-7-ethenyl-1,1,4a,7-tetramethyl-1,2,3,4,4a,4b,5,6,7,9,10,10a-dodecahydrophenanthren-2-ol
Other name(s): CYP76M6
Systematic name: ent-sandaracopimaradien-3β-ol,[reduced NADPH—hemoprotein reductase]:oxygen oxidoreductase (oryzalexin E forming)
Comments: A cytochrome P-450 (heme-thiolate) protein. Isolated from Oryza sativa (rice). Oryzalexin E is a phytoalexin.
Links to other databases: BRENDA, EXPASY, KEGG, MetaCyc
References:
1.  Wu, Y., Wang, Q., Hillwig, M.L. and Peters, R.J. Picking sides: distinct roles for CYP76M6 and CYP76M8 in rice oryzalexin biosynthesis. Biochem. J. 454 (2013) 209–216. [DOI] [PMID: 23795884]
[EC 1.14.14.122 created 2014 as EC 1.14.13.192, transferred 2018 to EC 1.14.14.122]
 
 
EC 1.14.14.123     
Accepted name: oryzalexin D synthase
Reaction: ent-sandaracopimaradien-3β-ol + [reduced NADPH—hemoprotein reductase] + O2 = oryzalexin D + [oxidized NADPH—hemoprotein reductase] + H2O
For diagram of oryzalexins biosynthesis, click here
Glossary: oryzalexin D = ent-sandaracopimaradiene-3β,7α-diol = (3R,4aR,4bS,7S,9S,10aS)-7-ethenyl-1,1,4a,7-tetramethyl-1,2,3,4,4a,4b,5,6,7,9,10,10a-dodecahydrophenanthren-2,9-diol
ent-sandaracopimaradien-3β-ol = (3R,4aR,4bR,7S,10aS)-7-ethenyl-1,1,4a,7-tetramethyl-1,2,3,4,4a,4b,5,6,7,9,10,10a-dodecahydrophenanthren-2-ol
Other name(s): CYP76M8
Systematic name: ent-sandaracopimaradien-3β-ol,[reduced NADPH—hemoprotein reductase]:oxygen oxidoreductase (oryzalexin D forming)
Comments: A cytochrome P-450 (heme-thiolate) protein. Isolated from Oryza sativa (rice). Oryzalexin D is a phytoalexin.
Links to other databases: BRENDA, EXPASY, KEGG, MetaCyc
References:
1.  Wu, Y., Wang, Q., Hillwig, M.L. and Peters, R.J. Picking sides: distinct roles for CYP76M6 and CYP76M8 in rice oryzalexin biosynthesis. Biochem. J. 454 (2013) 209–216. [DOI] [PMID: 23795884]
[EC 1.14.14.123 created 2014 as EC 1.14.13.193, transferred 2018 to EC 1.14.14.123]
 
 
EC 4.2.3.29     
Accepted name: ent-sandaracopimaradiene synthase
Reaction: ent-copalyl diphosphate = ent-sandaracopimara-8(14),15-diene + diphosphate
For diagram of the biosynthesis of diterpenoids from ent-copalyl diphosphate, click here
Other name(s): OsKS10; ent-sandaracopimara-8(14),15-diene synthase
Systematic name: ent-copalyl-diphosphate diphosphate-lyase [ent-sandaracopimara-8(14),15-diene-forming]
Comments: ent-Sandaracopimaradiene is a precursor of the rice oryzalexins A-F. Phytoalexins are diterpenoid secondary metabolites that are involved in the defense mechanism of the plant, and are produced in response to pathogen attack through the perception of elicitor signal molecules such as chitin oligosaccharide, or after exposure to UV irradiation. As a minor product, this enzyme also forms ent-pimara-8(14),15-diene, which is the sole product of EC 4.2.3.30, ent-pimara-8(14),15-diene synthase. ent-Pimara-8(14),15-diene is not a precursor in the biosynthesis of either gibberellins or phytoalexins [2].
Links to other databases: BRENDA, EXPASY, KEGG, MetaCyc
References:
1.  Otomo, K., Kanno, Y., Motegi, A., Kenmoku, H., Yamane, H., Mitsuhashi, W., Oikawa, H., Toshima, H., Itoh, H., Matsuoka, M., Sassa, T. and Toyomasu, T. Diterpene cyclases responsible for the biosynthesis of phytoalexins, momilactones A, B, and oryzalexins A-F in rice. Biosci. Biotechnol. Biochem. 68 (2004) 2001–2006. [DOI] [PMID: 15388982]
2.  Kanno, Y., Otomo, K., Kenmoku, H., Mitsuhashi, W., Yamane, H., Oikawa, H., Toshima, H., Matsuoka, M., Sassa, T. and Toyomasu, T. Characterization of a rice gene family encoding type-A diterpene cyclases. Biosci. Biotechnol. Biochem. 70 (2006) 1702–1710. [DOI] [PMID: 16861806]
[EC 4.2.3.29 created 2008]
 
 
EC 4.2.3.30     
Accepted name: ent-pimara-8(14),15-diene synthase
Reaction: ent-copalyl diphosphate = ent-pimara-8(14),15-diene + diphosphate
For diagram of the biosynthesis of diterpenoids from ent-copalyl diphosphate, click here
Other name(s): OsKS5
Systematic name: ent-copalyl-diphosphate diphosphate-lyase [ent-pimara-8(14),15-diene-forming]
Comments: Unlike EC 4.2.3.29, ent-sandaracopimaradiene synthase, which can produce both ent-sandaracopimaradiene and ent-pimara-8(14),15-diene, this diterpene cyclase produces only ent-pimara-8(14),15-diene. ent-Pimara-8(14),15-diene is not a precursor in the biosynthesis of either gibberellins or phytoalexins.
Links to other databases: BRENDA, EXPASY, KEGG, MetaCyc
References:
1.  Kanno, Y., Otomo, K., Kenmoku, H., Mitsuhashi, W., Yamane, H., Oikawa, H., Toshima, H., Matsuoka, M., Sassa, T. and Toyomasu, T. Characterization of a rice gene family encoding type-A diterpene cyclases. Biosci. Biotechnol. Biochem. 70 (2006) 1702–1710. [DOI] [PMID: 16861806]
[EC 4.2.3.30 created 2008]
 
 
EC 4.2.3.99     
Accepted name: labdatriene synthase
Reaction: 9α-copalyl diphosphate = (12E)-9α-labda-8(17),12,14-triene + diphosphate
For diagram of diterpenoids from 9α-copalyl diphosphate, click here
Glossary: 9α-copalyl diphosphate = syn-copalyl diphosphate = (2E)-3-methyl-5-[(1R,4aS,8aS)-5,5,8a-trimethyl-2-methylidenedecahydronaphthalen-1-yl]pent-2-en-1-yl trihydrogen diphosphate
(12E)-9α-labda-8(17),12,14-triene = (4aS,5R,8aS)-1,1,4a-trimethyl-6-methylidene-5-[(2E)-3-methylpenta-2,4-dien-1-yl]decahydronaphthalene
Other name(s): OsKSL10 (gene name)
Systematic name: 9α-copalyl-diphosphate diphosphate-lyase [(12E)-9α-labda-8(17),12,14-triene-forming]
Comments: The enzyme from rice (Oryza sativa), expressed in Escherichia coli, also produces ent-sandaracopimara-8(14),15-diene from ent-copalyl diphosphate, another naturally occuring copalyl isomer in rice (cf. ent-sandaracopimaradiene synthase, EC 4.2.3.29).
Links to other databases: BRENDA, EXPASY, KEGG, MetaCyc
References:
1.  Morrone, D., Hillwig, M.L., Mead, M.E., Lowry, L., Fulton, D.B. and Peters, R.J. Evident and latent plasticity across the rice diterpene synthase family with potential implications for the evolution of diterpenoid metabolism in the cereals. Biochem. J. 435 (2011) 589–595. [DOI] [PMID: 21323642]
[EC 4.2.3.99 created 2012]
 
 


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