2.5.1.9: riboflavin synthase
This is an abbreviated version!
For detailed information about riboflavin synthase, go to the full flat file.
Word Map on EC 2.5.1.9
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2.5.1.9
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6,7-dimethyl-8-ribityllumazine
-
cyclohydrolase
-
5-amino-6-ribitylamino-2,41h,3h-pyrimidinedione
-
dismutation
-
guilliermondii
-
3,4-dihydroxy-2-butanone
-
icosahedral
-
bartonellae
-
photobacterium
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flavinogenic
-
flavinogenesis
-
ashbyii
-
eremothecium
-
ribitylated
-
leiognathi
-
henselae
-
famata
-
drug development
-
pharmacology
-
medicine
- 2.5.1.9
- 6,7-dimethyl-8-ribityllumazine
-
cyclohydrolase
-
5-amino-6-ribitylamino-2,41h,3h-pyrimidinedione
-
dismutation
- guilliermondii
- 3,4-dihydroxy-2-butanone
-
icosahedral
-
bartonellae
- photobacterium
-
flavinogenic
-
flavinogenesis
-
ashbyii
- eremothecium
-
ribitylated
- leiognathi
- henselae
- famata
- drug development
- pharmacology
- medicine
Reaction
2 6,7-dimethyl-8-(1-D-ribityl)lumazine = +
Synonyms
heavy riboflavin synthase, light riboflavin synthase, lumazine synthase/riboflavin synthase complex, RibD, RibE1, riboflavin synthase, riboflavin synthetase, riboflavine synthase, riboflavine synthetase, synthase, riboflavin
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Reference
Reference on EC 2.5.1.9 - riboflavin synthase
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Plaut, G.W.E.
Studies on the nature of the enzymic conversion of 6,7-dimethyl-8-ribityllumazine to riboflavin
J. Biol. Chem.
238
2225-2243
1963
Eremothecium gossypii, Saccharomyces cerevisiae, Escherichia coli, Eremothecium gossypii AG33
Wacker, H.; Harvey, R.A.; Winestock, C.H.; Plaut, G.W.E.
4-(1'-D-ribitylamino)-5-amino-2,6-dihydroxypyrimidine, the second product of the riboflavin synthetase reaction
J. Biol. Chem.
239
3493-3497
1964
Saccharomyces cerevisiae
Plaut, G.W.E.; Harvey, R.A.
The enzymatic synthesis of riboflavin
Methods Enzymol.
18B
515-538
1971
Klebsiella aerogenes, Eremothecium gossypii, Bacillus subtilis, Saccharomyces cerevisiae, Escherichia coli, Lactiplantibacillus plantarum, Neurospora crassa, Pseudomonas sp.
-
Suzuki, Y.; Nishikawa, Y.; Mitsuda, H.
Catalytic properties of riboflavin synthetase from a high-riboflavinogenic Eremothecium ashbyii
J. Nutr. Sci. Vitaminol.
20
301-316
1974
Eremothecium ashbyi
Mitsuda, H.; Kawai, F.; Suzuki, Y.
Assay methods, isolation procedures, and catalytic properties of riboflavin synthetase from spinach
Methods Enzymol.
18B
539-543
1971
Saccharomyces cerevisiae, Spinacia oleracea
-
Harzer, G.; Rokos, H.; Otto, M.K.; Bacher, A.; Ghisla, S.
Biosynthesis of riboflavin. 6,7-Dimethyl-8-ribityllumazine 5-phosphate is not a substrate for riboflavin synthase
Biochim. Biophys. Acta
540
48-54
1978
Bacillus subtilis, Escherichia coli
Suzuki, A.; Goto, M.
Photolumazines, new naturally occurring inhibitors of riboflavin synthetase
Biochim. Biophys. Acta
313
229-234
1973
Eremothecium ashbyi
Ladenstein, R.; Ludwig, H.C.; Bacher, A.
Crystallization and preliminary X-ray diffraction study of heavy riboflavin synthase from Bacillus subtilis
J. Biol. Chem.
258
11981-11983
1983
Bacillus subtilis
Neuberger, G.; Bacher, A.
Biosynthesis of riboflavin. Enzymatic formation of 6,7-dimethyl-8-ribityllumazine by heavy riboflavin synthase from Bacillus subtilis
Biochem. Biophys. Res. Commun.
139
1111-1116
1986
Bacillus subtilis
Ladenstein, R.; Schneider, M.; Huber, R.; Bartunik, H.D.; Wilson, K.; Schott, K.; Bacher, A.
Heavy riboflavin synthase from Bacillus subtilis. Crystal structure analysis of the icosahedral beta 60 capsid at 3.3 A resolution
J. Mol. Biol.
203
1045-1070
1988
Bacillus subtilis
Schott, K.; Kellermann, J.; Lottspeich, F.; Bacher, A.
Riboflavin synthases of Bacillus subtilis. Purification and amino acid sequence of the alpha subunit
J. Biol. Chem.
265
4204-4209
1990
Bacillus subtilis
Bacher, A.; Baur, R.; Eggers, U.; Harders, H.D.; Otto, M.K.; Schnepple, H.
Riboflavin synthases of Bacillus subtilis. Purification and properties
J. Biol. Chem.
255
632-637
1980
Bacillus licheniformis, Bacillus subtilis, Escherichia coli, Escherichia coli B / ATCC 11303, Lactiplantibacillus plantarum, Moorella thermoacetica, Paenibacillus polymyxa, Priestia megaterium, Pseudomonas iodinum, Rhodococcus ruber, Saccharomyces cerevisiae, Streptomyces venezuelae
Bacher, A.
Heavy riboflavin synthase from Bacillus subtilis
Methods Enzymol.
122
192-199
1986
Bacillus subtilis
Ludwig, H.C.; Lottspeich, F.; Henschen, A.; Ladenstein, R.; Bacher, A.
Heavy riboflavin synthase of Bacillus subtilis. Primary structure of the beta subunit
J. Biol. Chem.
262
1016-1021
1987
Bacillus subtilis
Mitsuda, H.; Nakajima, K.; Nadamoto, T.; Yamada, Y.
Riboflavin synthetase from Eremothecium ashbyii and a salvage pathway of the by-product in the enzyme reaction
Methods Enzymol.
66
307-323
1980
Eremothecium ashbyi
Suzuki, Y.; Terai, Y.; Abe, S.
Purification and some properties of riboflavin synthetase from Bacillus stearothermophilus ATCC 8005
Appl. Environ. Microbiol.
35
258-263
1978
Geobacillus stearothermophilus
Kis, K.; Bacher, A.
Substrate channeling in the lumazine synthase/riboflavin synthase complex of Bacillus subtilis
J. Biol. Chem.
270
16788-16795
1995
Bacillus subtilis
Eberhardt, S.; Korn, S.; Lottspeich, F.; Bacher, A.
Biosynthesis of riboflavin: an unusual riboflavin synthase of Methanobacterium thermoautotrophicum
J. Bacteriol.
179
2938-2943
1997
Methanothermobacter thermautotrophicus (Q59587), Methanothermobacter thermautotrophicus, Methanothermobacter thermautotrophicus Marburg / DSM 2133 (Q59587)
Illarionov, B.; Kemter, K.; Eberhardt, S.; Richter, G.; Cushman, M.; Bacher, A.
Riboflavin synthase of Escherichia coli. Effect of single amino acid substitutions on reaction rate and ligand binding properties
J. Biol. Chem.
276
11524-11530
2001
Escherichia coli
Truffault, V.; Coles, M.; Diercks, T.; Abelmann, K.; Eberhardt, S.; Luttgen, H.; Bacher, A.; Kessler, H.
The solution structure of the N-terminal domain of riboflavin synthase
J. Mol. Biol.
309
949-960
2001
Escherichia coli (P0AFU8), Escherichia coli
Liao, D.I.; Wawrzak, Z.; Calabrese, J.C.; Viitanen, P.V.; Jordan, D.B.
Crystal structure of riboflavin synthase
Structure
9
399-408
2001
Escherichia coli, no activity in Homo sapiens
Eberhardt, S.; Zingler, N.; Kemter, K.; Richter, G.; Cushman, M.; Bacher, A.
Domain structure of riboflavin synthase
Eur. J. Biochem.
268
4315-4323
2001
Escherichia coli
Gerhardt, S.; Schott, A.K.; Kairies, N.; Cushman, M.; Illarionov, B.; Eisenreich, W.; Bacher, A.; Huber, R.; Steinbacher, S.; Fischer, M.
Studies on the reaction mechanism of riboflavin synthase: X-ray crystal structure of a complex with 6-carboxyethyl-7-oxo-8-ribityllumazine
Structure
10
1371-1381
2002
Schizosaccharomyces pombe (Q9Y7P0), Schizosaccharomyces pombe
Cushman, M.; Yang, D.; Gerhardt, S.; Huber, R.; Fischer, M.; Kis, K.; Bacher, A.
Design, synthesis, and evaluation of 6-carboxyalkyl and 6-phosphonoxyalkyl derivatives of 7-oxo-8-ribitylaminolumazines as inhibitors of riboflavin synthase and lumazine synthase
J. Org. Chem.
67
5807-5816
2002
Escherichia coli
Cushman, M.; Yang, D.; Mihalic, J.T.; Chen, J.; Gerhardt, S.; Huber, R.; Fischer, M.; Kis, K.; Bacher, A.
Incorporation of an amide into 5-phosphonoalkyl-6-D-ribitylaminopyrimidinedione lumazine synthase inhibitors results in an unexpected reversal of selectivity for riboflavin synthase vs lumazine synthase
J. Org. Chem.
67
6871-6877
2002
Escherichia coli
Fischer, M.; Romisch, W.; Illarionov, B.; Eisenreich, W.; Bacher, A.
Structures and reaction mechanisms of riboflavin synthases of eubacterial and archaeal origin
Biochem. Soc. Trans.
33
780-784
2005
Arabidopsis thaliana, Escherichia coli, Methanocaldococcus jannaschii, Methanothermobacter thermautotrophicus, Schizosaccharomyces pombe
Illarionov, B.; Haase, I.; Fischer, M.; Bacher, A.; Schramek, N.
Pre-steady-state kinetic analysis of riboflavin synthase using a pentacyclic reaction intermediate as substrate
Biol. Chem.
386
127-136
2005
Escherichia coli
Fischer, M.; Haase, I.; Feicht, R.; Schramek, N.; Kohler, P.; Schieberle, P.; Bacher, A.
Evolution of vitamin B2 biosynthesis: riboflavin synthase of Arabidopsis thaliana and its inhibition by riboflavin
Biol. Chem.
386
417-428
2005
Arabidopsis thaliana
Fischer, M.; Schott, A.K.; Kemter, K.; Feicht, R.; Richter, G.; Illarionov, B.; Eisenreich, W.; Gerhardt, S.; Cushman, M.; Steinbacher, S.; Huber, R.; Bacher, A.
Riboflavin synthase of Schizosaccharomyces pombe. Protein dynamics revealed by 19F NMR protein perturbation experiments
BMC Biochem.
4
18
2003
Schizosaccharomyces pombe (Q9Y7P0), Schizosaccharomyces pombe
Illarionov, B.; Haase, I.; Bacher, A.; Fischer, M.; Schramek, N.
Presteady state kinetic analysis of riboflavin synthase
J. Biol. Chem.
278
47700-47706
2003
Escherichia coli
Meining, W.; Eberhardt, S.; Bacher, A.; Ladenstein, R.
The structure of the N-terminal domain of riboflavin synthase in complex with riboflavin at 2.6 A resolution
J. Mol. Biol.
331
1053-1063
2003
Escherichia coli (P0AFU8), Escherichia coli
Fischer, M.; Schott, A.K.; Romisch, W.; Ramsperger, A.; Augustin, M.; Fidler, A.; Bacher, A.; Richter, G.; Huber, R.; Eisenreich, W.
Evolution of vitamin B2 biosynthesis. A novel class of riboflavin synthase in Archaea
J. Mol. Biol.
343
267-278
2004
Methanocaldococcus jannaschii, Methanocaldococcus jannaschii (Q58584)
Grill, S.; Yamaguchi, H.; Wagner, H.; Zwahlen, L.; Kusch, U.; Mack, M.
Identification and characterization of two Streptomyces davawensis riboflavin biosynthesis gene clusters
Arch. Microbiol.
188
377-387
2007
Streptomyces davaonensis (Q2VCE7), Streptomyces davaonensis
Lee, C.Y.; Illarionov, B.; Woo, Y.E.; Kemter, K.; Kim, R.R.; Eberhardt, S.; Cushman, M.; Eisenreich, W.; Fischer, M.; Bacher, A.
Ligand binding properties of the N-terminal domain of riboflavin synthase from Escherichia coli
J. Biochem. Mol. Biol.
40
239-246
2007
Escherichia coli
Talukdar, A.; Illarionov, B.; Bacher, A.; Fischer, M.; Cushman, M.
Synthesis and enzyme inhibitory activity of the s-nucleoside analogue of the ribitylaminopyrimidine substrate of lumazine synthase and product of riboflavin synthase
J. Org. Chem.
72
7167-7175
2007
Escherichia coli, Mycobacterium tuberculosis
Zhang, Y.; Illarionov, B.; Morgunova, E.; Jin, G.; Bacher, A.; Fischer, M.; Ladenstein, R.; Cushman, M.
A new series of N-[2,4-dioxo-6-d-ribitylamino-1,2,3,4-tetrahydropyrimidin-5-yl]oxalamic acid derivatives as inhibitors of lumazine synthase and riboflavin synthase: design, synthesis, biochemical evaluation, crystallography, and mechanistic implications
J. Org. Chem.
73
2715-2724
2008
Escherichia coli
Kim, R.R.; Illarionov, B.; Joshi, M.; Cushman, M.; Lee, C.Y.; Eisenreich, W.; Fischer, M.; Bacher, A.
Mechanistic insights on riboflavin synthase inspired by selective binding of the 6,7-dimethyl-8-ribityllumazine exomethylene anion
J. Am. Chem. Soc.
132
2983-2990
2010
Escherichia coli
Zhao, Y.; Bacher, A.; Illarionov, B.; Fischer, M.; Georg, G.; Ye, Q.Z.; Fanwick, P.E.; Franzblau, S.G.; Wan, B.; Cushman, M.
Discovery and development of the covalent hydrates of trifluoromethylated pyrazoles as riboflavin synthase inhibitors with antibiotic activity against Mycobacterium tuberculosis
J. Org. Chem.
74
5297-5303
2009
Mycobacterium tuberculosis, Escherichia coli (P0AFU8), Escherichia coli
Tuan, P.A.; Kim, J.K.; Lee, S.; Chae, S.C.; Park, S.U.
Riboflavin accumulation and characterization of cDNAs encoding lumazine synthase and riboflavin synthase in bitter melon (Momordica charantia)
J. Agric. Food Chem.
60
11980-11986
2012
Momordica charantia (L0C7R1), Momordica charantia
Talukdar, A.; Zhao, Y.; Lv, W.; Bacher, A.; Illarionov, B.; Fischer, M.; Cushman, M.
O-Nucleoside, S-nucleoside, and N-nucleoside probes of lumazine synthase and riboflavin synthase
J. Org. Chem.
77
6239-6261
2012
Escherichia coli, Mycobacterium tuberculosis
Kim, R.; Yi, J.; Nam, K.; Ko, K.; Lee, C.
Spectrofluorometric characteristics of the N-terminal domain of riboflavin synthase
Korean J. Microbiol.
47
14-21
2011
Escherichia coli
-
Higa, A.; Khandakar, J.; Mori, Y.; Kitamura, Y.
Increased de novo riboflavin synthesis and hydrolysis of FMN are involved in riboflavin secretion from Hyoscyamus albus hairy roots under iron deficiency
Plant Physiol. Biochem.
58
166-173
2012
Hyoscyamus albus (I7GUL1), Hyoscyamus albus
Illarionov, B.; Eisenreich, W.; Schramek, N.; Bacher, A.; Fischer, M.
Biosynthesis of vitamin B2: diastereomeric reaction intermediates of archaeal and non-archaeal riboflavin synthases
J. Biol. Chem.
280
28541-28546
2005
Escherichia coli, Methanocaldococcus jannaschii
Ramsperger, A.; Augustin, M.; Schott, A.K.; Gerhardt, S.; Krojer, T.; Eisenreich, W.; Illarionov, B.; Cushman, M.; Bacher, A.; Huber, R.; Fischer, M.
Crystal structure of an archaeal pentameric riboflavin synthase in complex with a substrate analog inhibitor: stereochemical implications
J. Biol. Chem.
281
1224-1232
2006
Methanocaldococcus jannaschii (Q58584), Methanocaldococcus jannaschii, Methanocaldococcus jannaschii DSM 2661 (Q58584)
Serer, M.I.; Bonomi, H.R.; Guimaraes, B.G.; Rossi, R.C.; Goldbaum, F.A.; Klinke, S.
Crystallographic and kinetic study of riboflavin synthase from Brucella abortus, a chemotherapeutic target with an enhanced intrinsic flexibility
Acta Crystallogr. Sect. D
70
1419-1434
2014
Brucella abortus (Q2YN92), Brucella abortus, Brucella abortus 2308 (Q2YN92)
Zhao, Y.; Wang, D.; Wu, T.; Guo, A.; Dong, H.; Zhang, C.
Transgenic expression of a rice riboflavin synthase gene in tobacco enhances plant growth and resistance to Tobacco mosaic virus
Can. J. Plant Pathol.
36
100-109
2014
Oryza sativa
-
Ladenstein, R.; Fischer, M.; Bacher, A.
The lumazine synthase/riboflavin synthase complex: shapes and functions of a highly variable enzyme system
FEBS J.
280
2537-2563
2013
Bacillus subtilis, Methanocaldococcus jannaschii, Methanothermobacter thermautotrophicus
Tuan, P.; Zhao, S.; Kim, J.; Kim, Y.; Yang, J.; Li, C.; Kim, S.; Arasu, M.; Al-Dhabi, N.; Park, S.
Riboflavin accumulation and molecular characterization of cDNAs encoding bifunctional GTP cyclohydrolase II/3,4-dihydroxy-2-butanone 4-phosphate synthase, lumazine synthase, and riboflavin synthase in different organs of Lycium chinense plant
Molecules
19
17141-17153
2014
Lycium chinense (W0FI48)
Kissling, L.; Schneider, C.; Seibel, K.; Dorjjugder, N.; Busche, T.; Kalinowski, J.; Mack, M.
The roseoflavin producer Streptomyces davaonensis has a high catalytic capacity and specific genetic adaptations with regard to the biosynthesis of riboflavin
Environ. Microbiol.
22
3248-3265
2020
Streptomyces davaonensis
Serer, M.I.; Carrica, M.D.C.; Trappe, J.; Lopez Romero, S.; Bonomi, H.R.; Klinke, S.; Cerutti, M.L.; Goldbaum, F.A.
A high-throughput screening for inhibitors of riboflavin synthase identifies novel antimicrobial compounds to treat brucellosis
FEBS J.
286
2522-2535
2019
Brucella abortus
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