Entry |
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Name |
Phosphonate and phosphinate metabolism - Burkholderia cenocepacia J2315
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Description |
Natural products containing carbon-phosphorous bonds, so-called C-P compounds, are derivatives of phosphonate and phosphinate with substitution of alkyl group for hydrogen of phosphorus-hydrogen bonds. C-P compounds have been found in many organisms, but only protists and bacteria, mostly Actinobacteria, have biosynthetic capacity. A common reaction in the biosynthetic pathway is C-P bond forming reaction from phosphoenolpyruvate (PEP) to phosphonopyruvate (PnPy) catalyzed by PEP phosphomutase. 2-Aminoethylphosphonate (AEP) is the most abundant C-P compound in the natural world. AEP derivatives include phosphonoprotein, phosphonoglycan, and phosphonolipid. Other known C-P compounds are bioactive substances used in medicine (antibiotics) and agriculture (herbicide) such as fosfomycin, FR-33289, rhizocticin, and bialaphos.
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Class |
Metabolism; Metabolism of other amino acids
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Pathway map |
bcj00440 | Phosphonate and phosphinate metabolism |

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Other DBs |
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Organism |
Burkholderia cenocepacia J2315 [GN: bcj]
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Gene |
BCAM1245 | putative phosphoenolpyruvate phosphomutase/sugar nucleotidyltransferase [KO:K01841] [EC:5.4.2.9] |
BCAL0451 | putative NADP-dependent glyceraldehyde-3-phosphate dehydrogenase [KO:K00206] [EC:1.2.1.-] |
BCAM2493 | putative NADP-dependent glyceraldehyde-3-phosphate dehydrogenase [KO:K00206] [EC:1.2.1.-] |
BCAM1186 | putative NADP-dependent glyceraldehyde-3-phosphate dehydrogenase [KO:K00206] [EC:1.2.1.-] |
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Compound |
C01151 | D-Ribose 1,5-bisphosphate |
C03557 | 2-Aminoethylphosphonate |
C05672 | 2-Amino-3-phosphonopropanoate |
C05673 | CMP-2-aminoethylphosphonate |
C05674 | CMP-N-trimethyl-2-aminoethylphosphonate |
C05675 | Diacylglyceryl-2-aminoethylphosphonate |
C05676 | Diacylglyceryl-N-trimethyl-2-aminoethylphosphonate |
C05678 | (2-Amino-1-hydroxyethyl)phosphonate |
C05679 | N-Monomethyl-2-aminoethylphosphonate |
C05680 | N-Dimethyl-2-aminoethylphosphonate |
C05681 | Ceramide 2-aminoethylphosphonate |
C06367 | 1-Carboxyvinyl carboxyphosphonate |
C06368 | 3-(Hydrohydroxyphosphoryl)pyruvate |
C06451 | 2-Hydroxyethylphosphonate |
C06455 | Hydroxymethylphosphonate |
C06459 | N-Trimethyl-2-aminoethylphosphonate |
C17941 | 2-Oxo-4-phosphonobutanoate |
C17947 | 2-Phosphinomethylmalate |
C17948 | Deamino-alpha-keto-demethylphosphinothricin |
C17949 | N-Acetyldemethylphosphinothricin |
C17950 | N-Acetyldemethylphosphinothricin tripeptide |
C17952 | N-Acetylphosphinothricin |
C17962 | Demethylphosphinothricin |
C20422 | alpha-D-Ribose 1-methylphosphonate 5-triphosphate |
C20423 | alpha-D-Ribose 1-methylphosphonate 5-phosphate |
C20440 | alpha-D-Ribose 1,2-cyclic phosphate 5-phosphate |
C20986 | D-Ribose 2,5-bisphosphate |
C21372 | 3-Phosphinomethylmalate |
C21403 | 2-Acetamidoethylphosphonate |
C21613 | (R)-2-(Phosphonomethyl)malate |
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Reference |
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Authors |
Metcalf WW, van der Donk WA |
Title |
Biosynthesis of phosphonic and phosphinic acid natural products. |
Journal |
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Reference |
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Authors |
Xiao Y, Lee K, Liu P |
Title |
Syntheses of the P-methylase substrates of the bialaphos biosynthetic pathway. |
Journal |
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Reference |
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Authors |
van der Donk WA |
Title |
Rings, radicals, and regeneration: the early years of a bioorganic laboratory. |
Journal |
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Reference |
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Authors |
Blodgett JA, Zhang JK, Metcalf WW |
Title |
Molecular cloning, sequence analysis, and heterologous expression of the phosphinothricin tripeptide biosynthetic gene cluster from Streptomyces viridochromogenes DSM 40736. |
Journal |
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Reference |
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Authors |
Schwartz D, Berger S, Heinzelmann E, Muschko K, Welzel K, Wohlleben W |
Title |
Biosynthetic gene cluster of the herbicide phosphinothricin tripeptide from Streptomyces viridochromogenes Tu494. |
Journal |
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Related pathway |
bcj00260 | Glycine, serine and threonine metabolism |
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KO pathway |
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LinkDB |
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