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rde00440                    Pathway                                

Phosphonate and phosphinate metabolism - Roseobacter denitrificans
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.
Metabolism; Metabolism of other amino acids
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rde00440  Phosphonate and phosphinate metabolism

Ortholog table
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BSID: 36835
GO: 0019634
Roseobacter denitrificans [GN:rde]
RD1_2037  acetyltransferase, putative [KO:K03823] [EC:]
RD1_2392  phnI; phosphonate metabolism protein, putative [KO:K06164] [EC:]
RD1_2394  phnG; alkylphosphonate utilization protein PhnG [KO:K06166] [EC:]
RD1_2393  phnH; phosphonate metabolism protein, putative [KO:K06165] [EC:]
RD1_2389  phnL; phosphonate C-P lyase system protein PhnL [KO:K05780] [EC:]
RD1_2387  phnM; phosphonate metabolism protein PhnM [KO:K06162] [EC:]
RD1_3512  phosphonate metabolism domain protein [KO:K06162] [EC:]
RD1_2391  phosphonate metabolism protein PhnJ [KO:K06163] [EC:]
RD1_3469  conserved hypothetical protein [KO:K06167] [EC:]
C00022  Pyruvate
C00033  Acetate
C00037  Glycine
C00074  Phosphoenolpyruvate
C00084  Acetaldehyde
C00117  D-Ribose 5-phosphate
C01151  D-Ribose 1,5-bisphosphate
C01438  Methane
C02798  3-Phosphonopyruvate
C03167  Phosphonoacetaldehyde
C03557  2-Aminoethylphosphonate
C04650  L-Phosphinothricin
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
C05677  Lipophosphonoglycan
C05678  (2-Amino-1-hydroxyethyl)phosphonate
C05679  N-Monomethyl-2-aminoethylphosphonate
C05680  N-Dimethyl-2-aminoethylphosphonate
C05681  Ceramide 2-aminoethylphosphonate
C05682  Phosphonoacetate
C05683  Ciliatocholate
C06367  1-Carboxyvinyl carboxyphosphonate
C06368  3-(Hydrohydroxyphosphoryl)pyruvate
C06451  2-Hydroxyethylphosphonate
C06452  (S)-2-Hydroxypropylphosphonate
C06454  Fosfomycin
C06455  Hydroxymethylphosphonate
C06456  Phosphonoformate
C06457  Bialaphos
C06459  N-Trimethyl-2-aminoethylphosphonate
C17940  Rhizocticin B
C17941  2-Oxo-4-phosphonobutanoate
C17942  FR 900098
C17943  Formylphosphonate
C17944  Rhizocticin A
C17945  Phosphonoformyl-CMP
C17947  2-Phosphinomethylmalate
C17948  Deamino-alpha-keto-demethylphosphinothricin
C17949  N-Acetyldemethylphosphinothricin
C17950  N-Acetyldemethylphosphinothricin tripeptide
C17951  N-Acetylbialaphos
C17952  N-Acetylphosphinothricin
C17960  Rhizocticin C
C17961  Rhizocticin D
C17962  Demethylphosphinothricin
C20396  Methylphosphonate
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
C21404  N-Ethylacetamide
C21613  (R)-2-(Phosphonomethyl)malate
Metcalf WW, van der Donk WA
Biosynthesis of phosphonic and phosphinic acid natural products.
Annu Rev Biochem 78:65-94 (2009)
Xiao Y, Lee K, Liu P
Syntheses of the P-methylase substrates of the bialaphos biosynthetic pathway.
Org Lett 10:5521-4 (2008)
van der Donk WA
Rings, radicals, and regeneration: the early years of a bioorganic laboratory.
J Org Chem 71:9561-71 (2006)
Blodgett JA, Zhang JK, Metcalf WW
Molecular cloning, sequence analysis, and heterologous expression of the phosphinothricin tripeptide biosynthetic gene cluster from Streptomyces viridochromogenes DSM 40736.
Antimicrob Agents Chemother 49:230-40 (2005)
Schwartz D, Berger S, Heinzelmann E, Muschko K, Welzel K, Wohlleben W
Biosynthetic gene cluster of the herbicide phosphinothricin tripeptide from Streptomyces viridochromogenes Tu494.
Appl Environ Microbiol 70:7093-102 (2004)
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