KEGG   PATHWAY: ko00440Help
Entry
ko00440                     Pathway                                

Name
Phosphonate and phosphinate metabolism
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.
Class
Metabolism; Metabolism of other amino acids
BRITE hierarchy
Pathway map
Phosphonate and phosphinate metabolism
ko00440

All organismsOrtholog table
Disease
H01821  
Spondylometaphyseal dysplasia with cone-rod dystrophy (SMD-CRD)
Other DBs
BSID: 
GO: 
Orthology
K01841  
phosphoenolpyruvate phosphomutase [EC:5.4.2.9]
K19669  
phosphonopyruvate hydrolase [EC:3.11.1.3]
K09459  
phosphonopyruvate decarboxylase [EC:4.1.1.82]
K05306  
phosphonoacetaldehyde hydrolase [EC:3.11.1.1]
K19670  
phosphonoacetate hydrolase [EC:3.11.1.2]
K03430  
2-aminoethylphosphonate-pyruvate transaminase [EC:2.6.1.37]
K09994  
aminoalkylphosphonate N-acetyltransferase [EC:2.3.1.-]
K21195  
2-aminoethylphosphonate dioxygenase [EC:1.14.11.46]
K21196  
2-amino-1-hydroxyethylphosphonate dioxygenase (glycine-forming) [EC:1.13.11.78]
K00967  
ethanolamine-phosphate cytidylyltransferase [EC:2.7.7.14]
K00993  
ethanolaminephosphotransferase [EC:2.7.8.1]
K13644  
choline/ethanolamine phosphotransferase [EC:2.7.8.2 2.7.8.1]
K00968  
choline-phosphate cytidylyltransferase [EC:2.7.7.15]
K00994  
diacylglycerol cholinephosphotransferase [EC:2.7.8.2]
K12901  
phosphonoacetaldehyde reductase
K12902  
phosphonoacetaldehyde methylase [EC:2.1.1.308]
K12903  
(S)-2-hydroxypropylphosphonic acid epoxidase [EC:1.11.1.23]
K12904  
phosphonoacetaldehyde reductase [EC:1.1.1.309]
K12905  
2-hydroxyethylphosphonate dioxygenase [EC:1.13.11.72]
K12906  
D-3-phosphoglycerate dehydrogenase
K12907  
aldehyde dehydrogenase
K12908  
phosphonoformate cytidylyltransferase [EC:2.7.7.93]
K12909  
carboxyvinyl-carboxyphosphonate phosphorylmutase [EC:2.7.8.23]
K12910  
2-phosphinomethylmalate synthase [EC:2.3.3.18]
K20930  
phosphinomethylmalate isomerase [EC:4.2.1.166]
K03823  
phosphinothricin acetyltransferase [EC:2.3.1.183]
K12911  
peptide synthetase PhsA
K12912  
peptide synthetase PhsB
K12913  
peptide synthetase PhsC
K12914  
P-methyltransferase [EC:2.1.1.326]
K12915  
phosphinothricin tripeptide acetyl hydrolase
K18049  
methylphosphonate synthase [EC:1.13.11.73]
K06164  
alpha-D-ribose 1-methylphosphonate 5-triphosphate synthase subunit PhnI [EC:2.7.8.37]
K06166  
alpha-D-ribose 1-methylphosphonate 5-triphosphate synthase subunit PhnG [EC:2.7.8.37]
K06165  
alpha-D-ribose 1-methylphosphonate 5-triphosphate synthase subunit PhnH [EC:2.7.8.37]
K05780  
alpha-D-ribose 1-methylphosphonate 5-triphosphate synthase subunit PhnL [EC:2.7.8.37]
K06162  
alpha-D-ribose 1-methylphosphonate 5-triphosphate diphosphatase [EC:3.6.1.63]
K06163  
alpha-D-ribose 1-methylphosphonate 5-phosphate C-P lyase [EC:4.7.1.1]
K06167  
phosphoribosyl 1,2-cyclic phosphate phosphodiesterase [EC:3.1.4.55]
K20859  
phosphoribosyl 1,2-cyclic phosphate 1,2-diphosphodiesterase [EC:3.1.4.57]
Compound
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
Reference
  Authors
Metcalf WW, van der Donk WA
  Title
Biosynthesis of phosphonic and phosphinic acid natural products.
  Journal
Annu Rev Biochem 78:65-94 (2009)
DOI:10.1146/annurev.biochem.78.091707.100215
Reference
  Authors
Xiao Y, Lee K, Liu P
  Title
Syntheses of the P-methylase substrates of the bialaphos biosynthetic pathway.
  Journal
Org Lett 10:5521-4 (2008)
DOI:10.1021/ol802269x
Reference
  Authors
van der Donk WA
  Title
Rings, radicals, and regeneration: the early years of a bioorganic laboratory.
  Journal
J Org Chem 71:9561-71 (2006)
DOI:10.1021/jo0614240
Reference
  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
Antimicrob Agents Chemother 49:230-40 (2005)
DOI:10.1128/AAC.49.1.230-240.2005
Reference
  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
Appl Environ Microbiol 70:7093-102 (2004)
DOI:10.1128/AEM.70.12.7093-7102.2004

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