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4-aminobenzoate + 5-phospho-alpha-D-ribose 1-diphosphate
4-(beta-D-ribofuranosyl)aminobenzene 5'-phosphate + CO2 + diphosphate
5-phospho-alpha-D-ribose 1-diphosphate + 4-amino-3,5-dicarboxypyrazole
4-amino-3-[(2S,3R,4S,5R)-3,4-dihydroxy-5-(oxophosphanyl)oxolan-2-yl]-1H-pyrazole-5-carboxylic acid + CO2 + diphosphate
5-phospho-alpha-D-ribose 1-diphosphate + 4-aminobenzoate
4-(beta-D-ribofuranosyl)aminobenzene 5'-phosphate + CO2 + diphosphate
5-phospho-alpha-D-ribose 1-diphosphate + 4-aminobenzoate
4-(beta-D-ribofuranosyl)aniline 5'-phosphate + CO2 + diphosphate
5-phospho-alpha-D-ribose 1-diphosphate + 4-aminobenzoate
beta-ribofuranosylaminobenzene 5'-phosphate + CO2 + diphosphate
-
-
-
-
?
5-phospho-alpha-D-ribose 1-diphosphate + 4-hydroxy-3,5-dicarboxypyrazole
3-[(2S,3R,4S,5R)-3,4-dihydroxy-5-(oxophosphanyl)oxolan-2-yl]-4-hydroxy-1H-pyrazole-5-carboxylic acid + CO2 + diphosphate
5-phospho-alpha-D-ribose 1-diphosphate + 4-hydroxybenzoate
4-(beta-D-ribofuranosyl)hydroxybenzene 5'-phosphate + CO2 + diphosphate
-
sequential pattern of substrate binding
-
-
?
5-phospho-alpha-D-ribose 1-diphosphate + 4-hydroxybenzoate
4-(beta-D-ribofuranosyl)phenol 5'-phosphate + CO2 + diphosphate
4-aminobenzoate + 5-phospho-alpha-D-ribose 1-diphosphate
4-(beta-D-ribofuranosyl)aminobenzene 5'-phosphate + CO2 + diphosphate
-
-
-
?
4-aminobenzoate + 5-phospho-alpha-D-ribose 1-diphosphate
4-(beta-D-ribofuranosyl)aminobenzene 5'-phosphate + CO2 + diphosphate
the enzyme is involved in biosynthesis of tetrahydromethanopterin, a folate analog involved in the C1 metabolism of methanogenic archaea, sulfate-reducing archaea, and methylotrophic bacteria
-
-
?
5-phospho-alpha-D-ribose 1-diphosphate + 4-amino-3,5-dicarboxypyrazole
4-amino-3-[(2S,3R,4S,5R)-3,4-dihydroxy-5-(oxophosphanyl)oxolan-2-yl]-1H-pyrazole-5-carboxylic acid + CO2 + diphosphate
-
-
-
-
?
5-phospho-alpha-D-ribose 1-diphosphate + 4-amino-3,5-dicarboxypyrazole
4-amino-3-[(2S,3R,4S,5R)-3,4-dihydroxy-5-(oxophosphanyl)oxolan-2-yl]-1H-pyrazole-5-carboxylic acid + CO2 + diphosphate
-
-
-
-
?
5-phospho-alpha-D-ribose 1-diphosphate + 4-aminobenzoate
4-(beta-D-ribofuranosyl)aminobenzene 5'-phosphate + CO2 + diphosphate
the enzyme is involved in biosynthesis of tetrahydromethanopterin, a folate analog involved in the C1 metabolism of methanogenic archaea, sulfate-reducing archaea, and methylotrophic bacteria
-
-
?
5-phospho-alpha-D-ribose 1-diphosphate + 4-aminobenzoate
4-(beta-D-ribofuranosyl)aminobenzene 5'-phosphate + CO2 + diphosphate
ordered Bi-Ter mechanism involving binding of 5-phospho-alpha-D-ribose 1-diphosphate, then 4-aminobenzoate, followed by release of the products CO2, then 4-(beta-D-ribofuranosyl)aminobenzene-5'-phosphate, and finally diphosphate
-
-
?
5-phospho-alpha-D-ribose 1-diphosphate + 4-aminobenzoate
4-(beta-D-ribofuranosyl)aminobenzene 5'-phosphate + CO2 + diphosphate
-
-
-
-
?
5-phospho-alpha-D-ribose 1-diphosphate + 4-aminobenzoate
4-(beta-D-ribofuranosyl)aminobenzene 5'-phosphate + CO2 + diphosphate
-
the enzyme is involved in biosynthesis of tetrahydromethanopterin, a folate analog involved in the C1 metabolism of methanogenic archaea, sulfate-reducing archaea, and methylotrophic bacteria
-
-
?
5-phospho-alpha-D-ribose 1-diphosphate + 4-aminobenzoate
4-(beta-D-ribofuranosyl)aminobenzene 5'-phosphate + CO2 + diphosphate
-
sequential pattern of substrate binding. An SN1-like reaction produces oxonium ion character at C-1 of 5-phospho-alpha-D-ribose 1-diphosphate which undergoes an ipso electrophilic aromatic substitution reaction at the carboxylic acid-bound carbon of 4-aminobenzoate. Decarboxylation of the resulting cyclohexadienimine intermediate leads to the formation of 4-(beta-D-ribofuranosyl)aminobenzene 5'-phosphate
-
-
?
5-phospho-alpha-D-ribose 1-diphosphate + 4-aminobenzoate
4-(beta-D-ribofuranosyl)aniline 5'-phosphate + CO2 + diphosphate
-
-
-
?
5-phospho-alpha-D-ribose 1-diphosphate + 4-aminobenzoate
4-(beta-D-ribofuranosyl)aniline 5'-phosphate + CO2 + diphosphate
-
-
-
-
?
5-phospho-alpha-D-ribose 1-diphosphate + 4-hydroxy-3,5-dicarboxypyrazole
3-[(2S,3R,4S,5R)-3,4-dihydroxy-5-(oxophosphanyl)oxolan-2-yl]-4-hydroxy-1H-pyrazole-5-carboxylic acid + CO2 + diphosphate
-
-
-
-
?
5-phospho-alpha-D-ribose 1-diphosphate + 4-hydroxy-3,5-dicarboxypyrazole
3-[(2S,3R,4S,5R)-3,4-dihydroxy-5-(oxophosphanyl)oxolan-2-yl]-4-hydroxy-1H-pyrazole-5-carboxylic acid + CO2 + diphosphate
-
-
-
-
?
5-phospho-alpha-D-ribose 1-diphosphate + 4-hydroxybenzoate
4-(beta-D-ribofuranosyl)phenol 5'-phosphate + CO2 + diphosphate
-
-
-
-
?
5-phospho-alpha-D-ribose 1-diphosphate + 4-hydroxybenzoate
4-(beta-D-ribofuranosyl)phenol 5'-phosphate + CO2 + diphosphate
-
-
-
-
?
5-phospho-alpha-D-ribose 1-diphosphate + 4-hydroxybenzoate
4-(beta-D-ribofuranosyl)phenol 5'-phosphate + CO2 + diphosphate
-
-
-
-
?
5-phospho-alpha-D-ribose 1-diphosphate + 4-hydroxybenzoate
4-(beta-D-ribofuranosyl)phenol 5'-phosphate + CO2 + diphosphate
-
-
-
-
?
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4-aminobenzoate + 5-phospho-alpha-D-ribose 1-diphosphate
4-(beta-D-ribofuranosyl)aminobenzene 5'-phosphate + CO2 + diphosphate
the enzyme is involved in biosynthesis of tetrahydromethanopterin, a folate analog involved in the C1 metabolism of methanogenic archaea, sulfate-reducing archaea, and methylotrophic bacteria
-
-
?
5-phospho-alpha-D-ribose 1-diphosphate + 4-aminobenzoate
4-(beta-D-ribofuranosyl)aminobenzene 5'-phosphate + CO2 + diphosphate
5-phospho-alpha-D-ribose 1-diphosphate + 4-aminobenzoate
beta-ribofuranosylaminobenzene 5'-phosphate + CO2 + diphosphate
-
-
-
-
?
5-phospho-alpha-D-ribose 1-diphosphate + 4-hydroxybenzoate
4-(beta-D-ribofuranosyl)phenol 5'-phosphate + CO2 + diphosphate
5-phospho-alpha-D-ribose 1-diphosphate + 4-aminobenzoate
4-(beta-D-ribofuranosyl)aminobenzene 5'-phosphate + CO2 + diphosphate
the enzyme is involved in biosynthesis of tetrahydromethanopterin, a folate analog involved in the C1 metabolism of methanogenic archaea, sulfate-reducing archaea, and methylotrophic bacteria
-
-
?
5-phospho-alpha-D-ribose 1-diphosphate + 4-aminobenzoate
4-(beta-D-ribofuranosyl)aminobenzene 5'-phosphate + CO2 + diphosphate
-
the enzyme is involved in biosynthesis of tetrahydromethanopterin, a folate analog involved in the C1 metabolism of methanogenic archaea, sulfate-reducing archaea, and methylotrophic bacteria
-
-
?
5-phospho-alpha-D-ribose 1-diphosphate + 4-hydroxybenzoate
4-(beta-D-ribofuranosyl)phenol 5'-phosphate + CO2 + diphosphate
-
-
-
-
?
5-phospho-alpha-D-ribose 1-diphosphate + 4-hydroxybenzoate
4-(beta-D-ribofuranosyl)phenol 5'-phosphate + CO2 + diphosphate
-
-
-
-
?
5-phospho-alpha-D-ribose 1-diphosphate + 4-hydroxybenzoate
4-(beta-D-ribofuranosyl)phenol 5'-phosphate + CO2 + diphosphate
-
-
-
-
?
5-phospho-alpha-D-ribose 1-diphosphate + 4-hydroxybenzoate
4-(beta-D-ribofuranosyl)phenol 5'-phosphate + CO2 + diphosphate
-
-
-
-
?
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4-(beta-D-ribofuranosyl)aminobenzene 5'-phosphate
uncompetitive inhibition under varied 5-phospho-alpha-D-ribose 1-diphosphate and saturated 4-aminobenzoate or under varied 4-aminobenzoate and saturated 5-phospho-alpha-D-ribose 1-diphosphate
4-(methylamino)benzoic acid
-
5 mM, complete loss of activity
4-aminothiobenzoate
-
5 mM, 24% loss of activity
4-Bromobenzoate
-
5 mM, 60% loss of activity
4-hydroxybenzoate
-
5 mM, 88% loss of activity
4-Methoxybenzoate
-
5 mM, 55% loss of activity
4-methylaminobenzoate
5 mM, 26% inhibition
benzoate
-
5 mM, 31% loss of activity
CO2
uncompetitive inhibition under varied 5-phospho-alpha-D-ribose 1-diphosphate and saturated 4-aminobenzoate. Mixed type of inhibition under varied 4-aminobenzoate and saturated 5-phospho-alpha-D-ribose 1-diphosphate
phosphate
-
10 mM, 37% inhibition
pyridoxal 5'-phosphate
-
2.5 mM, 21% inhibition
ribose 5-phosphate
-
10 mM, 20% inhibition
Sodium cyanoborohydride
-
160 mM, complete inhibition, decreased production of 4-(beta-D-ribofuranosyl)aminobenzene 5'-phosphate and the accumulation of a reduced form of the proposed cyclohexadienimine reaction intermediates
additional information
-
no inhibition by carbonyl reagents, 4-aminobenzoic acid methyl ester, aniline, 4-aminobenzamide
-
diphosphate
competitive inhibition under saturated 5-phospho-alpha-D-ribose 1-diphosphate and varied 4-aminobenzoate. Mixed type of inhibition under varied 4-aminobenzoate and saturated 5-phospho-alpha-D-ribose 1-diphosphate
diphosphate
-
5 mM, 84% inhibition
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Rasche, M.E.; White, R.H.
Mechanism for the enzymatic formation of 4-(beta-D-ribofuranosyl)aminobenzene 5'-phosphate during the biosynthesis of methanopterin
Biochemistry
37
11343-1151
1998
Methanosarcina thermophila
brenda
Scott, J.W.; Rasche, M.E.
Purification, overproduction, and partial characterization of beta-RFAP synthase, a key enzyme in the methanopterin biosynthesis pathway
J. Bacteriol.
184
4442-4448
2002
Methanosarcina thermophila, Archaeoglobus fulgidus (O28190), Archaeoglobus fulgidus
brenda
Dumitru, R.V.; Ragsdale, S.W.
Mechanism of 4-(beta-D-ribofuranosyl)aminobenzene 5'-phosphate synthase, a key enzyme in the methanopterin biosynthetic pathway
J. Biol. Chem.
279
39389-39395
2004
Methanocaldococcus jannaschii (Q58822), Methanocaldococcus jannaschii
brenda
Bechard, M.E.; Chhatwal, S.; Garcia, R.E.; Rasche, M.E.
Application of a colorimetric assay to identify putative ribofuranosylaminobenzene 5-phosphate synthase genes expressed with activity in Escherichia coli
Biol. Proced. Online
5
69-77
2003
Methylorubrum extorquens, Archaeoglobus fulgidus (O28190), Archaeoglobus fulgidus
brenda
Bechard, M.E.; Farahani, P.; Greene, D.; Pham, A.; Orry, A.; Rasche, M.E.
Purification, kinetic characterization, and site-directed mutagenesis of Methanothermobacter thermautotrophicus RFAP synthase produced in Escherichia coli
AIMS Microbiol.
5
186-204
2019
Methanothermobacter thermautotrophicus
brenda
Zhang, M.; Zhang, P.; Xu, G.; Zhou, W.; Gao, Y.; Gong, R.; Cai, Y.; Cong, H.; Deng, Z.; Price, N.; Mao, X.; Chen, W.
Comparative investigation into formycin a and pyrazofurin a biosynthesis reveals branch pathways for the construction of C-nucleoside scaffolds
Appl. Environ. Microbiol.
86
e01971-19
2020
Streptomyces candidus, Streptomyces kaniharaensis, Streptomyces candidus NRRL 3601, Streptomyces kaniharaensis ATCC 21070
brenda