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1.14.11.38

Accepted name:

verruculogen synthase

Reaction:

fumitremorgin B + 2-oxoglutarate + 2 O₂ + reduced acceptor = verruculogen + succinate + CO₂ + H₂O + acceptor

For diagram of fumitremorgin alkaloid biosynthesis (part 2), click here

Glossary:

fumitremorgin B = (5aR,6S,12S,14aS)-5a,6-dihydroxy-9-methoxy-11-(3-methylbut-2-en-1-yl)-12-(2-methylprop-1-en-1-yl)-1,2,3,5a,6,11,12,14a-octahydro-5H,14H-pyrrolo[1′′,2′′:4′,5′]pyrazino[1′,2′:1,6]pyrido[3,4-b]indole-5,14-dione
verruculogen = (5R,10S,10aR,14aS,15bS)-10,10a-dihydroxy-6-methoxy-2,2-dimethyl-5-(2-methylprop-1-en-1-yl)-1,10,10a,14,14a,15b-hexahydro-12H-3,4-dioxa-5a,11a,15a-triazacycloocta[1,2,3-lm]indeno[5,6-b]fluorene-11,15(2H,13H)-dione

Other name(s):

fmtF (gene name); FmtOx1

Systematic name:

fumitremorgin B,2-oxoglutarate:oxygen oxidoreductase (verruculogen-forming)

Comments:

Requires Fe²⁺ and ascorbate. Found in the fungus Aspergillus fumigatus. Both atoms of a dioxygen molecule are incorporated into verruculogen [1,2]. Involved in the biosynthetic pathways of several indole alkaloids such as fumitremorgin A.

Links to other databases:

BRENDA, EXPASY, KEGG, MetaCyc, PDB

References:

1.	Steffan, N., Grundmann, A., Afiyatullov, S., Ruan, H. and Li, S.M. FtmOx1, a non-heme Fe(II) and α-ketoglutarate-dependent dioxygenase, catalyses the endoperoxide formation of verruculogen in Aspergillus fumigatus. Org. Biomol. Chem. 7 (2009) 4082–4087. [DOI] [PMID: 19763315]
2.	Kato, N., Suzuki, H., Takagi, H., Uramoto, M., Takahashi, S. and Osada, H. Gene disruption and biochemical characterization of verruculogen synthase of Aspergillus fumigatus. ChemBioChem 12 (2011) 711–714. [DOI] [PMID: 21404415]

[EC 1.14.11.38 created 2013]

1.14.13.177

Transferred entry:

fumitremorgin C monooxygenase. Now EC 1.14.14.119, fumitremorgin C monooxygenase

[EC 1.14.13.177 created 2013, deleted 2018]

1.14.14.119

Accepted name:

fumitremorgin C monooxygenase

Reaction:

fumitremorgin C + 2 [reduced NADPH—hemoprotein reductase] + 2 O₂ = 12α,13α-dihydroxyfumitremorgin C + 2 [oxidized NADPH—hemoprotein reductase] + 2 H₂O

For diagram of fumitremorgin alkaloid biosynthesis (part 2), click here

Glossary:

fumitremorgin C = (5aS,12S,14aS)-9-methoxy-12-(2-methylprop-1-en-1-yl)-1,2,3,5a,6,11,12,14a-octahydro-5H,14H-pyrrolo[1′′,2′′:4′,5′]pyrazino[1′,2′:1,6]pyrido[3,4-b]indole-5,14-dione
12α,13α-dihydroxyfumitremorgin = (5aR,6S,12S,14aS)-5a,6-dihydroxy-9-methoxy-12-(2-methylprop-1-en-1-yl)-1,2,3,5a,6,11,12,14a-octahydro-5H,14H-pyrrolo[1′′,2′′:4′,5′]pyrazino[1′,2′:1,6]pyrido[3,4-b]indole-5,14-dione

Other name(s):

ftmG (gene name)

Systematic name:

fumitremorgin C,[reduced NADPH—hemoprotein reductase]:oxygen oxidoreductase (12α,13α-dihydroxyfumitremorgin C-forming)

Comments:

A cytochrome P-450 (heme-thiolate) protein. Involved in the biosynthetic pathway of the indole alkaloid verruculogen.

Links to other databases:

BRENDA, EXPASY, KEGG, MetaCyc

References:

1.	Kato, N., Suzuki, H., Takagi, H., Asami, Y., Kakeya, H., Uramoto, M., Usui, T., Takahashi, S., Sugimoto, Y. and Osada, H. Identification of cytochrome P450s required for fumitremorgin biosynthesis in Aspergillus fumigatus. ChemBioChem 10 (2009) 920–928. [DOI] [PMID: 19226505]

[EC 1.14.14.119 created 2013 as EC 1.14.13.177, transferred 2018 to EC 1.14.14.119]

1.14.19.71

Accepted name:

fumitremorgin C synthase

Reaction:

tryprostatin A + [reduced NADPH—hemoprotein reductase] + O₂ = fumitremorgin C + [oxidized NADPH—hemoprotein reductase] + 2 H₂O

For diagram of fumitremorgin alkaloid biosynthesis (part 1), click here

Glossary:

tryprostatin A = (3S,8aS)-3-{[6-methoxy-2-(3-methylbut-2-en-1-yl)-1H-indol-3-yl]methyl}hexahydropyrrolo[1,2-a]pyrazine-1,4-dione
fumitremorgin C = (5aS,12S,14aS)-9-methoxy-12-(2-methylprop-1-en-1-yl)-1,2,3,5a,6,11,12,14a-octahydro-5H,14H-pyrrolo[1′′,2′′:4′,5′]pyrazino[1′,2′:1,6]pyrido[3,4-b]indole-5,14-dione

Other name(s):

ftmE (gene name)

Systematic name:

tryprostatin A,[reduced NADPH—hemoprotein reductase]:oxygen oxidoreductase

Comments:

A cytochrome P-450 (heme-thiolate) protein. The protein from the fungus Aspergillus fumigatus also has activity with tryprostatin B forming demethoxyfumitremorgin C. Involved in the biosynthetic pathways of several indole alkaloids such as fumitremorgins and verruculogen.

Links to other databases:

BRENDA, EXPASY, KEGG, MetaCyc

References:

1.	Kato, N., Suzuki, H., Takagi, H., Asami, Y., Kakeya, H., Uramoto, M., Usui, T., Takahashi, S., Sugimoto, Y. and Osada, H. Identification of cytochrome P450s required for fumitremorgin biosynthesis in Aspergillus fumigatus. ChemBioChem 10 (2009) 920–928. [DOI] [PMID: 19226505]

[EC 1.14.19.71 created 2013 as EC 1.14.21.10, transferred 2018 to EC 1.14.19.71]

1.14.21.10

Transferred entry:

fumitremorgin C synthase. Now EC 1.14.19.71, fumitremorgin C synthase

[EC 1.14.21.10 created 2013, deleted 2018]

2.1.1.193

Accepted name:

16S rRNA (uracil¹⁴⁹⁸-N³)-methyltransferase

Reaction:

S-adenosyl-L-methionine + uracil¹⁴⁹⁸ in 16S rRNA = S-adenosyl-L-homocysteine + N³-methyluracil¹⁴⁹⁸ in 16S rRNA

For diagram of fumitremorgin alkaloid biosynthesis (part 1), click here

Other name(s):

DUF558 protein; YggJ; RsmE; m³U¹⁴⁹⁸ specific methyltransferase

Systematic name:

S-adenosyl-L-methionine:16S rRNA (uracil¹⁴⁹⁸-N³)-methyltransferase

Comments:

The enzyme specifically methylates uracil¹⁴⁹⁸ at N³ in 16S rRNA.

Links to other databases:

BRENDA, EXPASY, KEGG, MetaCyc, PDB

References:

1.	Basturea, G.N., Rudd, K.E. and Deutscher, M.P. Identification and characterization of RsmE, the founding member of a new RNA base methyltransferase family. RNA 12 (2006) 426–434. [DOI] [PMID: 16431987]
2.	Basturea, G.N. and Deutscher, M.P. Substrate specificity and properties of the Escherichia coli 16S rRNA methyltransferase, RsmE. RNA 13 (2007) 1969–1976. [DOI] [PMID: 17872509]

[EC 2.1.1.193 created 2010]

2.1.1.293

Accepted name:

6-hydroxytryprostatin B O-methyltransferase

Reaction:

S-adenosyl-L-methionine + 6-hydroxytryprostatin B = S-adenosyl-L-homocysteine + tryprostatin A

For diagram of fumitremorgin alkaloid biosynthesis (part 1), click here

Glossary:

6-hydroxytryprostatin B = (3S,8aS)-3-{[6-hydroxy-2-(3-methylbut-2-en-1-yl)-1H-indol-3-yl]methyl}hexahydropyrrolo[1,2-a]pyrazine-1,4-dione
tryprostatin A = (3S,8aS)-3-{[6-methoxy-2-(3-methylbut-2-en-1-yl)-1H-indol-3-yl]methyl}hexahydropyrrolo[1,2-a]pyrazine-1,4-dione

Other name(s):

ftmD (gene name)

Systematic name:

S-adenosyl-L-methionine:6-hydroxytryprostatin B O-methyltransferase

Comments:

Involved in the biosynthetic pathways of several indole alkaloids such as tryprostatins, fumitremorgins and verruculogen.

Links to other databases:

BRENDA, EXPASY, KEGG, MetaCyc

References:

1.	Kato, N., Suzuki, H., Okumura, H., Takahashi, S. and Osada, H. A point mutation in ftmD blocks the fumitremorgin biosynthetic pathway in Aspergillus fumigatus strain Af293. Biosci. Biotechnol. Biochem. 77 (2013) 1061–1067. [DOI] [PMID: 23649274]

[EC 2.1.1.293 created 2013]

2.5.1.106

Accepted name:

tryprostatin B synthase

Reaction:

prenyl diphosphate + brevianamide F = diphosphate + tryprostatin B

For diagram of fumitremorgin alkaloid biosynthesis (part 1), click here

Glossary:

brevianamide F = (3S,8aS)-3-(1H-indol-3-ylmethyl)hexahydropyrrolo[1,2-a]pyrazine-1,4-dione
tryprostatin B = (3S,8aS)-3-{[2-(3-methylbut-2-en-1-yl)-1H-indol-3-yl]methyl}hexahydropyrrolo[1,2-a]pyrazine-1,4-dione

Other name(s):

ftmPT1 (gene name); brevianamide F prenyltransferase (ambiguous); dimethylallyl-diphosphate:brevianamide-F dimethylallyl-C-2-transferase

Systematic name:

prenyl-diphosphate:brevianamide-F prenyl-C-2-transferase

Comments:

The enzyme from the fungus Aspergillus fumigatus can also prenylate other tryptophan-containing cyclic dipeptides. Prenylation occurs mainly at C-2 [1], but also at C-3 [2]. Involved in the biosynthetic pathways of several indole alkaloids such as tryprostatins, cyclotryprostatins, spirotryprostatins, fumitremorgins and verruculogen.

Links to other databases:

BRENDA, EXPASY, KEGG, MetaCyc, PDB

References:

1.	Grundmann, A. and Li, S.M. Overproduction, purification and characterization of FtmPT1, a brevianamide F prenyltransferase from Aspergillus fumigatus. Microbiology 151 (2005) 2199–2207. [DOI] [PMID: 16000710]
2.	Wollinsky, B., Ludwig, L., Xie, X. and Li, S.M. Breaking the regioselectivity of indole prenyltransferases: identification of regular C3-prenylated hexahydropyrrolo[2,3-b]indoles as side products of the regular C2-prenyltransferase FtmPT1. Org. Biomol. Chem. 10 (2012) 9262–9270. [DOI] [PMID: 23090579]

[EC 2.5.1.106 created 2013]

2.5.1.107

Accepted name:

verruculogen prenyltransferase

Reaction:

prenyl diphosphate + verruculogen = diphosphate + fumitremorgin A

For diagram of fumitremorgin alkaloid biosynthesis (part 2), click here

Glossary:

prenyl diphosphate = dimethylallyl diphosphate
verruculogen = (5R,10S,10aR,14aS,15bS)-10,10a-dihydroxy-6-methoxy-2,2-dimethyl-5-(2-methylprop-1-en-1-yl)-1,10,10a,14,14a,15b-hexahydro-12H-3,4-dioxa-5a,11a,15a-triazacycloocta[1,2,3-lm]indeno[5,6-b]fluorene-11,15(2H,13H)-dione
fumitremorgin A = (5R,10S,10aR,14aS,15bS)-10a-hydroxy-7-methoxy-2,2-dimethyl-10-[(3-methylbut-2-en-1-yl)oxy]-5-(2-methylprop-1-en-1-yl)-1,10,10a,14,14a,15b-hexahydro-12H-3,4-dioxa-5a,11a,15a-triazacycloocta[1,2,3-lm]indeno[5,6-b]fluorene-11,15(H,13H)-dione

Other name(s):

FtmPT3; dimethylallyl-diphosphate:verruculogen dimethylallyl-O-transferase

Systematic name:

prenyl-diphosphate:verruculogen dimethylallyl-O-transferase

Comments:

Found in a number of fungi. Catalyses the last step in the biosynthetic pathway of the indole alkaloid fumitremorgin A. The enzyme from the fungus Neosartorya fischeri is also active with fumitremorgin B and 12α,13α-dihydroxyfumitremorgin C.

Links to other databases:

BRENDA, EXPASY, KEGG, MetaCyc

References:

1.	Mundt, K., Wollinsky, B., Ruan, H.L., Zhu, T. and Li, S.M. Identification of the verruculogen prenyltransferase FtmPT3 by a combination of chemical, bioinformatic and biochemical approaches. ChemBioChem 13 (2012) 2583–2592. [DOI] [PMID: 23109474]

[EC 2.5.1.107 created 2013]

2.5.1.109

Accepted name:

brevianamide F prenyltransferase (deoxybrevianamide E-forming)

Reaction:

prenyl diphosphate + brevianamide F = diphosphate + deoxybrevianamide E

For diagram of fumitremorgin alkaloid biosynthesis (part 1), click here

Glossary:

brevianamide F = (3S,8aS)-3-(1H-indol-3-ylmethyl)hexahydropyrrolo[1,2-a]pyrazine-1,4-dione
deoxybrevianamide E = (3S,8aS)-3-{[2-(2-methylbut-3-en-2-yl)-1H-indol-3-yl]methyl}-octahydropyrrolo[1,2-a]piperazine-1,4-dione

Other name(s):

NotF; BrePT; brevianamide F reverse prenyltransferase; dimethylallyl-diphosphate:brevianamide-F tert-dimethylallyl-C-2-transferase

Systematic name:

prenyl-diphosphate:brevianamide-F 2-methylbut-3-en-2-yl-C-2-transferase

Comments:

The enzyme from the fungus Aspergilus sp. MF297-2 is specific for brevianamide F [1], while the enzyme from Aspergillus versicolor accepts a broad range of trytophan-containing cyclic dipeptides [2]. Involved in the biosynthetic pathways of several indole alkaloids such as paraherquamides and malbrancheamides.

Links to other databases:

BRENDA, EXPASY, KEGG, MetaCyc, PDB

References:

Ding, Y., de Wet, J.R., Cavalcoli, J., Li, S., Greshock, T.J., Miller, K.A., Finefield, J.M., Sunderhaus, J.D., McAfoos, T.J., Tsukamoto, S., Williams, R.M. and Sherman, D.H. Genome-based characterization of two prenylation steps in the assembly of the stephacidin and notoamide anticancer agents in a marine-derived Aspergillus sp. J. Am. Chem. Soc. 132 (2010) 12733–12740. [DOI] [PMID: 20722388]

Yin, S., Yu, X., Wang, Q., Liu, X.Q. and Li, S.M. Identification of a brevianamide F reverse prenyltransferase BrePT from Aspergillus versicolor with a broad substrate specificity towards tryptophan-containing cyclic dipeptides. Appl. Microbiol. Biotechnol. 97 (2013) 1649–1660. [DOI] [PMID: 22660767]

[EC 2.5.1.109 created 2013]

2.5.1.110

Accepted name:

12α,13α-dihydroxyfumitremorgin C prenyltransferase

Reaction:

prenyl diphosphate + 12α,13α-dihydroxyfumitremorgin C = diphosphate + fumitremorgin B

For diagram of fumitremorgin alkaloid biosynthesis (part 2), click here

Glossary:

12α,13α-dihydroxyfumitremorgin = (5aR,6S,12S,14aS)-5a,6-dihydroxy-9-methoxy-12-(2-methylprop-1-en-1-yl)-1,2,3,5a,6,11,12,14a-octahydro-5H,14H-pyrrolo[1′′,2′′:4′,5′]pyrazino[1′,2′:1,6]pyrido[3,4-b]indole-5,14-dione
fumitremorgin B = (5aR,6S,12S,14aS)-5a,6-dihydroxy-9-methoxy-11-(3-methylbut-2-en-1-yl)-12-(2-methylprop-1-en-1-yl)-1,2,3,5a,6,11,12,14a-octahydro-5H,14H-pyrrolo[1′′,2′′:4′,5′]pyrazino[1′,2′:1,6]pyrido[3,4-b]indole-5,14-dione

Other name(s):

ftmH (gene name); FtmPT2; dimethylallyl-diphosphate:12α,13α-dihydroxyfumitremorgin C dimethylallyl-N-1-transferase

Systematic name:

prenyl-diphosphate:12α,13α-dihydroxyfumitremorgin C prenyl-N-1-transferase

Comments:

The enzyme from the fungus Aspergillus fumigatus also shows some activity with fumitremorgin C. Involved in the biosynthetic pathways of several indole alkaloids such as fumitremorgins and verruculogen.

Links to other databases:

BRENDA, EXPASY, KEGG, MetaCyc

References:

1.	Grundmann, A., Kuznetsova, T., Afiyatullov, S.Sh and Li, S.M. FtmPT2, an N-prenyltransferase from Aspergillus fumigatus, catalyses the last step in the biosynthesis of fumitremorgin B. ChemBioChem 9 (2008) 2059–2063. [DOI] [PMID: 18683158]

[EC 2.5.1.110 created 2013]