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6-(2-amino-2-carboxyethyl)-7,8-dioxo-1,2,3,4,7,8-hexahydroquinoline-2,4-dicarboxylate + 3 O2 = 4,5-dioxo-4,5-dihydro-1H-pyrrolo[2,3-f]quinoline-2,7,9-tricarboxylate + 2 H2O2 + 2 H2O
6-(2-amino-2-carboxyethyl)-7,8-dioxo-1,2,3,4,7,8-hexahydroquinoline-2,4-dicarboxylate + 3 O2 = 4,5-dioxo-4,5-dihydro-1H-pyrrolo[2,3-f]quinoline-2,7,9-tricarboxylate + 2 H2O2 + 2 H2O
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6-(2-amino-2-carboxyethyl)-7,8-dioxo-1,2,3,4,7,8-hexahydroquinoline-2,4-dicarboxylate + 3 O2 = 4,5-dioxo-4,5-dihydro-1H-pyrrolo[2,3-f]quinoline-2,7,9-tricarboxylate + 2 H2O2 + 2 H2O
PqqC is part of a complex of six enzymes that act together in pyrroloquinoline-quinone synthesis: PqqA serves as a complex precursor for for pyrroloquinoline-quinone synthesis, PqqB is not directly required for pyrroloquinoline-quinone biosynthesis, but a carrier and responsible for its transport across the plasma-membrane into the periplasm, PqqC does not contain a redox-active metal or other cofactor and is responsible for the last cyclization and oxidation steps in pyrroloquinoline-quinone synthesis, PqqD has three possible functions: first, it could play a role in the release of pyrroloquinoline-quinone from PqqC, second it could be involved in binding of PqqB to PqqC, third it could function as the dioxygenase in the pathway, PqqE is a family member of radical S-adenosylmethionine enzymes and catalyzes a radical driven C-C bond formation required to link the glutamate and tyrosine moieties at atoms C9 and C9a of pyrroloquinoline-quinone, PqqF recognizes and cleaves all four peptide bonds in PqqA
6-(2-amino-2-carboxyethyl)-7,8-dioxo-1,2,3,4,7,8-hexahydroquinoline-2,4-dicarboxylate + 3 O2 = 4,5-dioxo-4,5-dihydro-1H-pyrrolo[2,3-f]quinoline-2,7,9-tricarboxylate + 2 H2O2 + 2 H2O
PqqC is part of a complex of six enzymes that act together in pyrroloquinoline-quinone synthesis: PqqA serves as a complex precursor for for pyrroloquinoline-quinone synthesis, PqqB is not directly required for pyrroloquinoline-quinone biosynthesis, but a carrier and responsible for its transport across the plasma-membrane into the periplasm, PqqC does not contain a redox-active metal or other cofactor and is responsible for the the last cyclization and oxidation steps in pyrroloquinoline-quinone synthesis, PqqD has three possible functions: first, it could play a role in the release of pyrroloquinoline-quinone from PqqC, second it could be involved in binding of PqqB to PqqC, third it could function as the dioxygenase in the pathway, PqqE is a family member of radical S-adenosylmethionine enzymes and catalyzes a radical driven C-C bond formation required to link the glutamate and tyrosine moieties at atoms C9 and C9a of pyrroloquinoline-quinone, PqqF recognizes and cleaves all four peptide bonds in PqqA
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6-(2-amino-2-carboxyethyl)-7,8-dioxo-1,2,3,4,7,8-hexahydroquinoline-2,4-dicarboxylate + 3 O2 = 4,5-dioxo-4,5-dihydro-1H-pyrrolo[2,3-f]quinoline-2,7,9-tricarboxylate + 2 H2O2 + 2 H2O
PqqC is part of a complex of six enzymes that act together in pyrroloquinoline-quinone synthesis: PqqA serves as a complex precursor for for pyrroloquinoline-quinone synthesis, PqqB is not directly required for pyrroloquinoline-quinone biosynthesis, but a carrier and responsible for its transport across the plasma-membrane into the periplasm, PqqC does not contain a redox-active metal or other cofactorand is responsible for the the last cyclization and oxidation steps in pyrroloquinoline-quinone synthesis, PqqD has three possible functions: first, it could play a role in the release of pyrroloquinoline-quinone from PqqC, second it could be involved in binding of PqqB to PqqC, third it could function as the dioxygenase in the pathway, PqqE is a family member of radical S-adenosylmethionine enzymes and catalyzes a radical driven C-C bond formation required to link the glutamate and tyrosine moieties at atoms C9 and C9a of pyrroloquinoline-quinone, PqqF recognizes and cleaves all four peptide bonds in PqqA
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6-(2-amino-2-carboxyethyl)-7,8-dioxo-1,2,3,4,7,8-hexahydroquinoline-2,4-dicarboxylate + 3 O2 = 4,5-dioxo-4,5-dihydro-1H-pyrrolo[2,3-f]quinoline-2,7,9-tricarboxylate + 2 H2O2 + 2 H2O
PqqC/D produces the reduced pyrroloquinoline quinone from the intermediate in vivo
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6-(2-amino-2-carboxyethyl)-7,8-dioxo-1,2,3,4,7,8-hexahydroquinoline-2,4-dicarboxylate + 3 O2 = 4,5-dioxo-4,5-dihydro-1H-pyrrolo[2,3-f]quinoline-2,7,9-tricarboxylate + 2 H2O2 + 2 H2O
reaction mechanism consisting of a series of base catalyzed proton abstractions followed by quinoid/quinol tautomerizations and oxidations, overview
6-(2-amino-2-carboxyethyl)-7,8-dioxo-1,2,3,4,7,8-hexahydroquinoline-2,4-dicarboxylate + 3 O2 = 4,5-dioxo-4,5-dihydro-1H-pyrrolo[2,3-f]quinoline-2,7,9-tricarboxylate + 2 H2O2 + 2 H2O
reaction mechanism consisting of a series of base catalyzed proton abstractions followed by quinoid/quinol tautomerizations and oxidations, overview
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3a-(2-amino-2-carboxyethyl)-4,5-dioxo-4,5,6,7,8,9-hexahydroquinoline-7,9-dicarboxylic acid + O2
4,5-dioxo-1H-pyrrolo[2,3-f]quinoline-2,7,9-tricarboxylate + H2O2 + H2O
6-(2-amino-2-carboxyethyl)-7,8-dioxo-1,2,3,4,5,6,7,8,-octahydroquinoline-2,4-dicarboxylate + O2
4,5-dioxo-3a,4,5,6,7,8,9,9b-octahydro-1H-pyrrolo[2,3-f]quinoline-2,7,9-tricarboxylate + H2O2 + H2O
6-(2-amino-2-carboxyethyl)-7,8-dioxo-1,2,3,4,7,8-hexahydroquinoline-2,4-dicarboxylate + 3 O2
4,5-dioxo-1H-pyrrolo[2,3-f]quinoline-2,7,9-tricarboxylate + 2 H2O2 + 2 H2O
additional information
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3a-(2-amino-2-carboxyethyl)-4,5-dioxo-4,5,6,7,8,9-hexahydroquinoline-7,9-dicarboxylic acid + O2
4,5-dioxo-1H-pyrrolo[2,3-f]quinoline-2,7,9-tricarboxylate + H2O2 + H2O
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the product is pyrroloquinoline quinone (PQQ)
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3a-(2-amino-2-carboxyethyl)-4,5-dioxo-4,5,6,7,8,9-hexahydroquinoline-7,9-dicarboxylic acid + O2
4,5-dioxo-1H-pyrrolo[2,3-f]quinoline-2,7,9-tricarboxylate + H2O2 + H2O
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synthesis of the pyrroloquinoline quinone (PQQ), that serves as prosthetic group for many bacterial enzymes, PQQ might also be involved in the protection against reactive oxygen species during growth under stress conditions
the product is pyrroloquinoline quinone (PQQ)
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3a-(2-amino-2-carboxyethyl)-4,5-dioxo-4,5,6,7,8,9-hexahydroquinoline-7,9-dicarboxylic acid + O2
4,5-dioxo-1H-pyrrolo[2,3-f]quinoline-2,7,9-tricarboxylate + H2O2 + H2O
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the product is pyrroloquinoline quinone (PQQ)
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3a-(2-amino-2-carboxyethyl)-4,5-dioxo-4,5,6,7,8,9-hexahydroquinoline-7,9-dicarboxylic acid + O2
4,5-dioxo-1H-pyrrolo[2,3-f]quinoline-2,7,9-tricarboxylate + H2O2 + H2O
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synthesis of the pyrroloquinoline quinone (PQQ), that serves as prosthetic group for many bacterial enzymes, PQQ might also be involved in the protection against reactive oxygen species during growth under stress conditions
the product is pyrroloquinoline quinone (PQQ)
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3a-(2-amino-2-carboxyethyl)-4,5-dioxo-4,5,6,7,8,9-hexahydroquinoline-7,9-dicarboxylic acid + O2
4,5-dioxo-1H-pyrrolo[2,3-f]quinoline-2,7,9-tricarboxylate + H2O2 + H2O
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3a-(2-amino-2-carboxyethyl)-4,5-dioxo-4,5,6,7,8,9-hexahydroquinoline-7,9-dicarboxylic acid + O2
4,5-dioxo-1H-pyrrolo[2,3-f]quinoline-2,7,9-tricarboxylate + H2O2 + H2O
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3a-(2-amino-2-carboxyethyl)-4,5-dioxo-4,5,6,7,8,9-hexahydroquinoline-7,9-dicarboxylic acid + O2
4,5-dioxo-1H-pyrrolo[2,3-f]quinoline-2,7,9-tricarboxylate + H2O2 + H2O
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3a-(2-amino-2-carboxyethyl)-4,5-dioxo-4,5,6,7,8,9-hexahydroquinoline-7,9-dicarboxylic acid + O2
4,5-dioxo-1H-pyrrolo[2,3-f]quinoline-2,7,9-tricarboxylate + H2O2 + H2O
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the product is pyrroloquinoline quinone (PQQ)
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3a-(2-amino-2-carboxyethyl)-4,5-dioxo-4,5,6,7,8,9-hexahydroquinoline-7,9-dicarboxylic acid + O2
4,5-dioxo-1H-pyrrolo[2,3-f]quinoline-2,7,9-tricarboxylate + H2O2 + H2O
synthesis of the pyrroloquinoline quinone (PQQ), that serves as prosthetic group for many bacterial enzymes
the product is pyrroloquinoline quinone (PQQ)
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3a-(2-amino-2-carboxyethyl)-4,5-dioxo-4,5,6,7,8,9-hexahydroquinoline-7,9-dicarboxylic acid + O2
4,5-dioxo-1H-pyrrolo[2,3-f]quinoline-2,7,9-tricarboxylate + H2O2 + H2O
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3a-(2-amino-2-carboxyethyl)-4,5-dioxo-4,5,6,7,8,9-hexahydroquinoline-7,9-dicarboxylic acid + O2
4,5-dioxo-1H-pyrrolo[2,3-f]quinoline-2,7,9-tricarboxylate + H2O2 + H2O
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the product is pyrroloquinoline quinone (PQQ)
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?
3a-(2-amino-2-carboxyethyl)-4,5-dioxo-4,5,6,7,8,9-hexahydroquinoline-7,9-dicarboxylic acid + O2
4,5-dioxo-1H-pyrrolo[2,3-f]quinoline-2,7,9-tricarboxylate + H2O2 + H2O
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the product is pyrroloquinoline quinone (PQQ)
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3a-(2-amino-2-carboxyethyl)-4,5-dioxo-4,5,6,7,8,9-hexahydroquinoline-7,9-dicarboxylic acid + O2
4,5-dioxo-1H-pyrrolo[2,3-f]quinoline-2,7,9-tricarboxylate + H2O2 + H2O
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synthesis of the pyrroloquinoline quinone (PQQ), that serves as prosthetic group for many bacterial enzymes
the product is pyrroloquinoline quinone (PQQ)
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?
3a-(2-amino-2-carboxyethyl)-4,5-dioxo-4,5,6,7,8,9-hexahydroquinoline-7,9-dicarboxylic acid + O2
4,5-dioxo-1H-pyrrolo[2,3-f]quinoline-2,7,9-tricarboxylate + H2O2 + H2O
synthesis of the pyrroloquinoline quinone (PQQ), that serves as prosthetic group for many bacterial enzymes
the product is pyrroloquinoline quinone (PQQ)
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?
3a-(2-amino-2-carboxyethyl)-4,5-dioxo-4,5,6,7,8,9-hexahydroquinoline-7,9-dicarboxylic acid + O2
4,5-dioxo-1H-pyrrolo[2,3-f]quinoline-2,7,9-tricarboxylate + H2O2 + H2O
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the product is pyrroloquinoline quinone (PQQ)
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?
3a-(2-amino-2-carboxyethyl)-4,5-dioxo-4,5,6,7,8,9-hexahydroquinoline-7,9-dicarboxylic acid + O2
4,5-dioxo-1H-pyrrolo[2,3-f]quinoline-2,7,9-tricarboxylate + H2O2 + H2O
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synthesis of the pyrroloquinoline quinone (PQQ), that serves as prosthetic group for many bacterial enzymes
the product is pyrroloquinoline quinone (PQQ)
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?
3a-(2-amino-2-carboxyethyl)-4,5-dioxo-4,5,6,7,8,9-hexahydroquinoline-7,9-dicarboxylic acid + O2
4,5-dioxo-1H-pyrrolo[2,3-f]quinoline-2,7,9-tricarboxylate + H2O2 + H2O
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3a-(2-amino-2-carboxyethyl)-4,5-dioxo-4,5,6,7,8,9-hexahydroquinoline-7,9-dicarboxylic acid + O2
4,5-dioxo-1H-pyrrolo[2,3-f]quinoline-2,7,9-tricarboxylate + H2O2 + H2O
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the product is pyrroloquinoline quinone (PQQ)
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?
3a-(2-amino-2-carboxyethyl)-4,5-dioxo-4,5,6,7,8,9-hexahydroquinoline-7,9-dicarboxylic acid + O2
4,5-dioxo-1H-pyrrolo[2,3-f]quinoline-2,7,9-tricarboxylate + H2O2 + H2O
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synthesis of the pyrroloquinoline quinone (PQQ), that serves as prosthetic group for many bacterial enzymes
the product is pyrroloquinoline quinone (PQQ)
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?
3a-(2-amino-2-carboxyethyl)-4,5-dioxo-4,5,6,7,8,9-hexahydroquinoline-7,9-dicarboxylic acid + O2
4,5-dioxo-1H-pyrrolo[2,3-f]quinoline-2,7,9-tricarboxylate + H2O2 + H2O
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the product is pyrroloquinoline quinone (PQQ)
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?
3a-(2-amino-2-carboxyethyl)-4,5-dioxo-4,5,6,7,8,9-hexahydroquinoline-7,9-dicarboxylic acid + O2
4,5-dioxo-1H-pyrrolo[2,3-f]quinoline-2,7,9-tricarboxylate + H2O2 + H2O
synthesis of the pyrroloquinoline quinone (PQQ), that serves as prosthetic group for many bacterial enzymes
the product is pyrroloquinoline quinone (PQQ)
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?
3a-(2-amino-2-carboxyethyl)-4,5-dioxo-4,5,6,7,8,9-hexahydroquinoline-7,9-dicarboxylic acid + O2
4,5-dioxo-1H-pyrrolo[2,3-f]quinoline-2,7,9-tricarboxylate + H2O2 + H2O
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6-(2-amino-2-carboxyethyl)-7,8-dioxo-1,2,3,4,5,6,7,8,-octahydroquinoline-2,4-dicarboxylate + O2
4,5-dioxo-3a,4,5,6,7,8,9,9b-octahydro-1H-pyrrolo[2,3-f]quinoline-2,7,9-tricarboxylate + H2O2 + H2O
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6-(2-amino-2-carboxyethyl)-7,8-dioxo-1,2,3,4,5,6,7,8,-octahydroquinoline-2,4-dicarboxylate + O2
4,5-dioxo-3a,4,5,6,7,8,9,9b-octahydro-1H-pyrrolo[2,3-f]quinoline-2,7,9-tricarboxylate + H2O2 + H2O
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6-(2-amino-2-carboxyethyl)-7,8-dioxo-1,2,3,4,5,6,7,8,-octahydroquinoline-2,4-dicarboxylate + O2
4,5-dioxo-3a,4,5,6,7,8,9,9b-octahydro-1H-pyrrolo[2,3-f]quinoline-2,7,9-tricarboxylate + H2O2 + H2O
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6-(2-amino-2-carboxyethyl)-7,8-dioxo-1,2,3,4,5,6,7,8,-octahydroquinoline-2,4-dicarboxylate + O2
4,5-dioxo-3a,4,5,6,7,8,9,9b-octahydro-1H-pyrrolo[2,3-f]quinoline-2,7,9-tricarboxylate + H2O2 + H2O
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6-(2-amino-2-carboxyethyl)-7,8-dioxo-1,2,3,4,5,6,7,8,-octahydroquinoline-2,4-dicarboxylate + O2
4,5-dioxo-3a,4,5,6,7,8,9,9b-octahydro-1H-pyrrolo[2,3-f]quinoline-2,7,9-tricarboxylate + H2O2 + H2O
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6-(2-amino-2-carboxyethyl)-7,8-dioxo-1,2,3,4,7,8-hexahydroquinoline-2,4-dicarboxylate + 3 O2
4,5-dioxo-1H-pyrrolo[2,3-f]quinoline-2,7,9-tricarboxylate + 2 H2O2 + 2 H2O
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6-(2-amino-2-carboxyethyl)-7,8-dioxo-1,2,3,4,7,8-hexahydroquinoline-2,4-dicarboxylate + 3 O2
4,5-dioxo-1H-pyrrolo[2,3-f]quinoline-2,7,9-tricarboxylate + 2 H2O2 + 2 H2O
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6-(2-amino-2-carboxyethyl)-7,8-dioxo-1,2,3,4,7,8-hexahydroquinoline-2,4-dicarboxylate + 3 O2
4,5-dioxo-1H-pyrrolo[2,3-f]quinoline-2,7,9-tricarboxylate + 2 H2O2 + 2 H2O
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6-(2-amino-2-carboxyethyl)-7,8-dioxo-1,2,3,4,7,8-hexahydroquinoline-2,4-dicarboxylate + 3 O2
4,5-dioxo-1H-pyrrolo[2,3-f]quinoline-2,7,9-tricarboxylate + 2 H2O2 + 2 H2O
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6-(2-amino-2-carboxyethyl)-7,8-dioxo-1,2,3,4,7,8-hexahydroquinoline-2,4-dicarboxylate + 3 O2
4,5-dioxo-1H-pyrrolo[2,3-f]quinoline-2,7,9-tricarboxylate + 2 H2O2 + 2 H2O
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6-(2-amino-2-carboxyethyl)-7,8-dioxo-1,2,3,4,7,8-hexahydroquinoline-2,4-dicarboxylate + 3 O2
4,5-dioxo-1H-pyrrolo[2,3-f]quinoline-2,7,9-tricarboxylate + 2 H2O2 + 2 H2O
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additional information
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PqqC/D has low affinity to PQQH2
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additional information
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catalyzes the final step of PQQ formation, which involves a ring closure and an overall eight-electron oxidation of 3a-(2-amino-2-carboxyethyl)-4,5-dioxo-4,5,6,7,8,9-hexahydroquinoline-7,9-dicarboxylic acid in the absence of a redox-active metal or cofactor
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additional information
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PqqC/D produces the reduced pyrroloquinoline quinone from the intermediate in vivo
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additional information
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PqqC/D has low affinity to PQQH2
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additional information
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PqqC/D produces the reduced pyrroloquinoline quinone from the intermediate in vivo
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additional information
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PqqC/D has low affinity to PQQH2
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Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
3a-(2-amino-2-carboxyethyl)-4,5-dioxo-4,5,6,7,8,9-hexahydroquinoline-7,9-dicarboxylic acid + O2
4,5-dioxo-1H-pyrrolo[2,3-f]quinoline-2,7,9-tricarboxylate + H2O2 + H2O
6-(2-amino-2-carboxyethyl)-7,8-dioxo-1,2,3,4,5,6,7,8,-octahydroquinoline-2,4-dicarboxylate + O2
4,5-dioxo-3a,4,5,6,7,8,9,9b-octahydro-1H-pyrrolo[2,3-f]quinoline-2,7,9-tricarboxylate + H2O2 + H2O
6-(2-amino-2-carboxyethyl)-7,8-dioxo-1,2,3,4,7,8-hexahydroquinoline-2,4-dicarboxylate + 3 O2
4,5-dioxo-1H-pyrrolo[2,3-f]quinoline-2,7,9-tricarboxylate + 2 H2O2 + 2 H2O
additional information
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3a-(2-amino-2-carboxyethyl)-4,5-dioxo-4,5,6,7,8,9-hexahydroquinoline-7,9-dicarboxylic acid + O2
4,5-dioxo-1H-pyrrolo[2,3-f]quinoline-2,7,9-tricarboxylate + H2O2 + H2O
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synthesis of the pyrroloquinoline quinone (PQQ), that serves as prosthetic group for many bacterial enzymes, PQQ might also be involved in the protection against reactive oxygen species during growth under stress conditions
the product is pyrroloquinoline quinone (PQQ)
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?
3a-(2-amino-2-carboxyethyl)-4,5-dioxo-4,5,6,7,8,9-hexahydroquinoline-7,9-dicarboxylic acid + O2
4,5-dioxo-1H-pyrrolo[2,3-f]quinoline-2,7,9-tricarboxylate + H2O2 + H2O
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synthesis of the pyrroloquinoline quinone (PQQ), that serves as prosthetic group for many bacterial enzymes, PQQ might also be involved in the protection against reactive oxygen species during growth under stress conditions
the product is pyrroloquinoline quinone (PQQ)
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?
3a-(2-amino-2-carboxyethyl)-4,5-dioxo-4,5,6,7,8,9-hexahydroquinoline-7,9-dicarboxylic acid + O2
4,5-dioxo-1H-pyrrolo[2,3-f]quinoline-2,7,9-tricarboxylate + H2O2 + H2O
synthesis of the pyrroloquinoline quinone (PQQ), that serves as prosthetic group for many bacterial enzymes
the product is pyrroloquinoline quinone (PQQ)
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?
3a-(2-amino-2-carboxyethyl)-4,5-dioxo-4,5,6,7,8,9-hexahydroquinoline-7,9-dicarboxylic acid + O2
4,5-dioxo-1H-pyrrolo[2,3-f]quinoline-2,7,9-tricarboxylate + H2O2 + H2O
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synthesis of the pyrroloquinoline quinone (PQQ), that serves as prosthetic group for many bacterial enzymes
the product is pyrroloquinoline quinone (PQQ)
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?
3a-(2-amino-2-carboxyethyl)-4,5-dioxo-4,5,6,7,8,9-hexahydroquinoline-7,9-dicarboxylic acid + O2
4,5-dioxo-1H-pyrrolo[2,3-f]quinoline-2,7,9-tricarboxylate + H2O2 + H2O
synthesis of the pyrroloquinoline quinone (PQQ), that serves as prosthetic group for many bacterial enzymes
the product is pyrroloquinoline quinone (PQQ)
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?
3a-(2-amino-2-carboxyethyl)-4,5-dioxo-4,5,6,7,8,9-hexahydroquinoline-7,9-dicarboxylic acid + O2
4,5-dioxo-1H-pyrrolo[2,3-f]quinoline-2,7,9-tricarboxylate + H2O2 + H2O
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synthesis of the pyrroloquinoline quinone (PQQ), that serves as prosthetic group for many bacterial enzymes
the product is pyrroloquinoline quinone (PQQ)
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3a-(2-amino-2-carboxyethyl)-4,5-dioxo-4,5,6,7,8,9-hexahydroquinoline-7,9-dicarboxylic acid + O2
4,5-dioxo-1H-pyrrolo[2,3-f]quinoline-2,7,9-tricarboxylate + H2O2 + H2O
synthesis of the pyrroloquinoline quinone (PQQ), that serves as prosthetic group for many bacterial enzymes
the product is pyrroloquinoline quinone (PQQ)
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6-(2-amino-2-carboxyethyl)-7,8-dioxo-1,2,3,4,5,6,7,8,-octahydroquinoline-2,4-dicarboxylate + O2
4,5-dioxo-3a,4,5,6,7,8,9,9b-octahydro-1H-pyrrolo[2,3-f]quinoline-2,7,9-tricarboxylate + H2O2 + H2O
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6-(2-amino-2-carboxyethyl)-7,8-dioxo-1,2,3,4,5,6,7,8,-octahydroquinoline-2,4-dicarboxylate + O2
4,5-dioxo-3a,4,5,6,7,8,9,9b-octahydro-1H-pyrrolo[2,3-f]quinoline-2,7,9-tricarboxylate + H2O2 + H2O
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6-(2-amino-2-carboxyethyl)-7,8-dioxo-1,2,3,4,5,6,7,8,-octahydroquinoline-2,4-dicarboxylate + O2
4,5-dioxo-3a,4,5,6,7,8,9,9b-octahydro-1H-pyrrolo[2,3-f]quinoline-2,7,9-tricarboxylate + H2O2 + H2O
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6-(2-amino-2-carboxyethyl)-7,8-dioxo-1,2,3,4,5,6,7,8,-octahydroquinoline-2,4-dicarboxylate + O2
4,5-dioxo-3a,4,5,6,7,8,9,9b-octahydro-1H-pyrrolo[2,3-f]quinoline-2,7,9-tricarboxylate + H2O2 + H2O
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6-(2-amino-2-carboxyethyl)-7,8-dioxo-1,2,3,4,5,6,7,8,-octahydroquinoline-2,4-dicarboxylate + O2
4,5-dioxo-3a,4,5,6,7,8,9,9b-octahydro-1H-pyrrolo[2,3-f]quinoline-2,7,9-tricarboxylate + H2O2 + H2O
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6-(2-amino-2-carboxyethyl)-7,8-dioxo-1,2,3,4,7,8-hexahydroquinoline-2,4-dicarboxylate + 3 O2
4,5-dioxo-1H-pyrrolo[2,3-f]quinoline-2,7,9-tricarboxylate + 2 H2O2 + 2 H2O
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6-(2-amino-2-carboxyethyl)-7,8-dioxo-1,2,3,4,7,8-hexahydroquinoline-2,4-dicarboxylate + 3 O2
4,5-dioxo-1H-pyrrolo[2,3-f]quinoline-2,7,9-tricarboxylate + 2 H2O2 + 2 H2O
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6-(2-amino-2-carboxyethyl)-7,8-dioxo-1,2,3,4,7,8-hexahydroquinoline-2,4-dicarboxylate + 3 O2
4,5-dioxo-1H-pyrrolo[2,3-f]quinoline-2,7,9-tricarboxylate + 2 H2O2 + 2 H2O
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6-(2-amino-2-carboxyethyl)-7,8-dioxo-1,2,3,4,7,8-hexahydroquinoline-2,4-dicarboxylate + 3 O2
4,5-dioxo-1H-pyrrolo[2,3-f]quinoline-2,7,9-tricarboxylate + 2 H2O2 + 2 H2O
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6-(2-amino-2-carboxyethyl)-7,8-dioxo-1,2,3,4,7,8-hexahydroquinoline-2,4-dicarboxylate + 3 O2
4,5-dioxo-1H-pyrrolo[2,3-f]quinoline-2,7,9-tricarboxylate + 2 H2O2 + 2 H2O
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6-(2-amino-2-carboxyethyl)-7,8-dioxo-1,2,3,4,7,8-hexahydroquinoline-2,4-dicarboxylate + 3 O2
4,5-dioxo-1H-pyrrolo[2,3-f]quinoline-2,7,9-tricarboxylate + 2 H2O2 + 2 H2O
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additional information
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catalyzes the final step of PQQ formation, which involves a ring closure and an overall eight-electron oxidation of 3a-(2-amino-2-carboxyethyl)-4,5-dioxo-4,5,6,7,8,9-hexahydroquinoline-7,9-dicarboxylic acid in the absence of a redox-active metal or cofactor
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additional information
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PqqC/D produces the reduced pyrroloquinoline quinone from the intermediate in vivo
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additional information
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PqqC/D produces the reduced pyrroloquinoline quinone from the intermediate in vivo
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evolution
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the gene pqqC is a suitable molecular marker that can be used complementary to housekeeping genes for studying the diversity and evolution of plant-beneficial pseudomonads, phylogenetic tree, overview. Phylogenetic distribution of cultivated and noncultivated pseudomonads from wheat roots based on pqqC
evolution
phylogenetic analysis of the pqqC gene of species of the genus Pseudomonas reveals that strain JX22 differs significantly from other species with sequenced pqqC genes
evolution
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phylogenetic analysis of the pqqC gene of species of the genus Pseudomonas reveals that strain JX22 differs significantly from other species with sequenced pqqC genes
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malfunction
pqqC gene disruption mutant JX22MT1 by the EZ-Tn5 transposon mutation, the mutant shows no antifungal activity against Fusarium oxysporum f. sp. lycopersici in contrast to the wild-type strain JX22. Antifungal activity at wild-type level is restored by introduction of the functional wild-type pqqC gene
malfunction
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pqqC gene disruption mutant JX22MT1 by the EZ-Tn5 transposon mutation, the mutant shows no antifungal activity against Fusarium oxysporum f. sp. lycopersici in contrast to the wild-type strain JX22. Antifungal activity at wild-type level is restored by introduction of the functional wild-type pqqC gene
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metabolism
PqqC catalyzes the last step of pyrroloquinoline quinone biogenesis which involves a ring closure and an eight-electron oxidation of the substrate 3a-(2-amino-2-carboxyethyl)-4,5-dioxo-4,5,6,7,8,9-hexahydroquinoline-7,9-dicarboxylic acid
metabolism
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the enzyme catalyzes the final step of the pyrroloquinoline quinone biosynthesis, namely, cyclization and oxidation of the intermediate 3a-(2-amino-2-carboxy-ethyl)-4,5-dioxo-4,5,6,7,8,9-hexahydroquinoline-7,9-dicarboxylic acid to pyrroloquinoline quinone
metabolism
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PqqC catalyzes the last step of pyrroloquinoline quinone biogenesis which involves a ring closure and an eight-electron oxidation of the substrate 3a-(2-amino-2-carboxyethyl)-4,5-dioxo-4,5,6,7,8,9-hexahydroquinoline-7,9-dicarboxylic acid
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physiological function
pyrroloquinoline quinone, i.e. 4,5-dihydro-4,5-dioxo-1Hpyrrolo[2,3-f]quinoline-2,7,9-tricarboxylic acid, PQQ, synthesized by the enzyme, is a bacterial cofactor in numerous alcohol dehydrogenases including methanol dehydrogenase and glucose dehydrogenase
physiological function
enzyme Pqq C, encded by gene pqqC, is essential for antifungal activity of Pseudomonas kilonensis JX22 against Fusarium oxysporum f. sp. lycopersici. Strain JX22 shows broad range of antifungal and antibacterial activities to plant pathogens, e.g. it significantly inhibits mycelial growth of Fusarium oxysporum f. sp. lycopersici strain ATCC 9848
physiological function
the enzyme is involved in biosynthesis of pyrroloquinoline quinone, PQQ, a cofactor of various membrane-bound dehydrogenases. The amount of endogenous PQQ is generally regarded as a bottleneck to achieving higher catalytic efficiency of PQQ-dependent dehydrogenases. PQQ biosynthesis can be enhanced by overexpressing some of the individual genes in the gene cluster in Gluconobacter oxydans and the PQQ levels are positively correlated with the efficiency of conversion of D-sorbitol to L-sorbose, overexpression of PQQ-related genes activates L-sorbose production and D-sorbitol dehydrogenase activity
physiological function
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enzyme Pqq C, encded by gene pqqC, is essential for antifungal activity of Pseudomonas kilonensis JX22 against Fusarium oxysporum f. sp. lycopersici. Strain JX22 shows broad range of antifungal and antibacterial activities to plant pathogens, e.g. it significantly inhibits mycelial growth of Fusarium oxysporum f. sp. lycopersici strain ATCC 9848
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physiological function
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pyrroloquinoline quinone, i.e. 4,5-dihydro-4,5-dioxo-1Hpyrrolo[2,3-f]quinoline-2,7,9-tricarboxylic acid, PQQ, synthesized by the enzyme, is a bacterial cofactor in numerous alcohol dehydrogenases including methanol dehydrogenase and glucose dehydrogenase
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physiological function
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the enzyme is involved in biosynthesis of pyrroloquinoline quinone, PQQ, a cofactor of various membrane-bound dehydrogenases. The amount of endogenous PQQ is generally regarded as a bottleneck to achieving higher catalytic efficiency of PQQ-dependent dehydrogenases. PQQ biosynthesis can be enhanced by overexpressing some of the individual genes in the gene cluster in Gluconobacter oxydans and the PQQ levels are positively correlated with the efficiency of conversion of D-sorbitol to L-sorbose, overexpression of PQQ-related genes activates L-sorbose production and D-sorbitol dehydrogenase activity
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additional information
the enzyme has 14 conserved active site residues, which are in close contact with bound substrate pyrroloquinoline quinone. It exhibits a stepwise process in which substrate binding leads to the generation of the closed protein conformation, with the latter playing a critical role in O2 binding and catalysis
additional information
an all atom model of the quinoprotein dehydrogenase PqqC in complex with 4,5-dihydro-4,5-dioxo-1H-pyrrolo[2,3-f]quinoline-2,7,9-tricarboxylic acid (PQQ) and O2, solvated with TIP3 water in periodic boxes, is subjected to random-acceleration molecular dynamics (RAMD) showing that O2 leaves the active binding pocket, in front of PQQ, to get to the solvent, as easily as with a variety of other O2-activating enzymes, O2 carriers, and gas-sensing proteins. The shortest pathway, orthogonal to the center of the mean plane of PQQ, is largely preferred by O2 over pathways slightly deviating from this line. These observations challenge the interpretation of an impermeable active binding pocket of PqqC-PQQ, as drawn from both X-ray diffraction data of the crystal at low temperature and physiological experimentation. Key residues for the minor O2 gates are 1. Q155, L158, R177, and R17, 2. E188, and L191, and 3. D83 and Q182, or the main O2 egress involving residues P151, L180, and A183, modeling, overview
additional information
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the enzyme has 14 conserved active site residues, which are in close contact with bound substrate pyrroloquinoline quinone. It exhibits a stepwise process in which substrate binding leads to the generation of the closed protein conformation, with the latter playing a critical role in O2 binding and catalysis
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Toyama, H.; Fukumoto, H.; Saeki, M.; Matsushita, K.; Adachi, O.; Lidstrom, M.E.
PqqC/D, which converts a biosynthetic intermediate to pyrroloquinoline quinone
Biochem. Biophys. Res. Commun.
299
268-272
2002
Methylorubrum extorquens, Methylorubrum extorquens ATCC 14718 / DSM 1338 / JCM 2805 / NCIMB 9133 / AM1
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Khairnar, N.P.; Misra, H.S.; Apte, S.K.
Pyrroloquinoline-quinone synthesized in Escherichia coli by pyrroloquinoline-quinone synthase of Deinococcus radiodurans plays a role beyond mineral phosphate solubilization
Biochem. Biophys. Res. Commun.
312
303-308
2003
Deinococcus radiodurans, Deinococcus radiodurans KR1
brenda
Magnusson, O.T.; Toyama, H.; Saeki, M.; Schwarzenbacher, R.; Klinman, J.P.
The structure of a biosynthetic intermediate of pyrroloquinoline quinone (PQQ) and elucidation of the final step of PQQ biosynthesis
J. Am. Chem. Soc.
126
5342-5343
2004
Methylorubrum extorquens, Methylorubrum extorquens ATCC 14718 / DSM 1338 / JCM 2805 / NCIMB 9133 / AM1
brenda
Toyama, H.; Chistoserdova, L.; Lidstrom, M.E.
Sequence analysis of pqq genes required for biosynthesis of pyrroloquinoline quinone in Methylobacterium extorquens AM1 and the purification of a biosynthetic intermediate
Microbiology
143
595-602
1997
Methylorubrum extorquens (Q49150), Methylorubrum extorquens ATCC 14718 / DSM 1338 / JCM 2805 / NCIMB 9133 / AM1 (Q49150)
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Magnusson, O.T.; Toyama, H.; Saeki, M.; Rojas, A.; Reed, J.C.; Liddington, R.C.; Klinman, J.P.; Schwarzenbacher, R.
Quinone biogenesis: Structure and mechanism of PqqC, the final catalyst in the production of pyrroloquinoline quinone
Proc. Natl. Acad. Sci. USA
101
7913-7918
2004
Klebsiella pneumoniae (P27505)
brenda
Schwarzenbacher, R.; Stenner-Liewen, F.; Liewen, H.; Reed, J.C.; Liddington, R.C.
Crystal structure of PqqC from Klebsiella pneumoniae at 2.1 ANG resolution
Proteins
56
401-403
2004
Klebsiella pneumoniae (P27505)
brenda
Toyama, H.; Nishibayashi, E.; Saeki, M.; Adachi, O.; Matsushita, K.
Factors required for the catalytic reaction of PqqC/D which produces pyrroloquinoline quinone
Biochem. Biophys. Res. Commun.
354
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2007
Escherichia coli, Klebsiella pneumoniae, Methylorubrum extorquens, Methylorubrum extorquens ATCC 14718 / DSM 1338 / JCM 2805 / NCIMB 9133 / AM1
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12
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Pyrroloquinoline quinone biogenesis: characterization of PqqC and its H84N and H84A active site variants
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46
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2007
Klebsiella pneumoniae
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9
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77
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Structural studies of mutant forms of the PQQ-forming enzyme PqqC in the presence of product and substrate
Proteins
78
2554-2562
2010
Klebsiella pneumoniae (A6T9H1), Klebsiella pneumoniae MGH 78578 (A6T9H1)
brenda
Wang, P.; Xia, Y.; Li, J.; Kang, Z.; Zhou, J.; Chen, J.
Overexpression of pyrroloquinoline quinone biosynthetic genes affects L-sorbose production in Gluconobacter oxydans WSH-003
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112
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2016
Gluconobacter oxydans (Q9L3B2), Gluconobacter oxydans WSH-003 (Q9L3B2)
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On dioxygen permeation through a dehydrogenase-pyrroloquinoline quinone complex. A molecular-dynamics investigation
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11
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2014
Klebsiella pneumoniae (P27505)
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Xu, J.; Deng, P.; Showmaker, K.C.; Wang, H.; Baird, S.M.; Lu, S.E.
The pqqC gene is essential for antifungal activity of Pseudomonas kilonensis JX22 against Fusarium oxysporum f. sp. lycopersici
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353
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2014
Pseudomonas kilonensis (W5XLY8), Pseudomonas kilonensis JX22 (W5XLY8)
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