Entry 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 acidsBRITE hierarchy
Pathway map ko00440 Phosphonate and phosphinate metabolism
Other DBs Orthology K00206 phnY; phosphonoacetaldehyde dehydrogenase
K00967 PCYT2; ethanolamine-phosphate cytidylyltransferase [EC:2.7.7.14 ]
K00994 CHPT1, CPT1; diacylglycerol cholinephosphotransferase [EC:2.7.8.2 ]
K03430 phnW; 2-aminoethylphosphonate-pyruvate transaminase [EC:2.6.1.37 ]
K05780 phnL; alpha-D-ribose 1-methylphosphonate 5-triphosphate synthase subunit PhnL [EC:2.7.8.37 ]
K05915 phnZ1; (hydroxymethyl)phosphonate/2-amino-1-hydroxyethylphosphonate dioxygenase
K06162 phnM; alpha-D-ribose 1-methylphosphonate 5-triphosphate diphosphatase [EC:3.6.1.63 ]
K06163 phnJ; alpha-D-ribose 1-methylphosphonate 5-phosphate C-P lyase [EC:4.7.1.1 ]
K06164 phnI; alpha-D-ribose 1-methylphosphonate 5-triphosphate synthase subunit PhnI [EC:2.7.8.37 ]
K06165 phnH; alpha-D-ribose 1-methylphosphonate 5-triphosphate synthase subunit PhnH [EC:2.7.8.37 ]
K06166 phnG; alpha-D-ribose 1-methylphosphonate 5-triphosphate synthase subunit PhnG [EC:2.7.8.37 ]
K06167 phnP; phosphoribosyl 1,2-cyclic phosphate phosphodiesterase [EC:3.1.4.55 ]
K12901 fomC; phosphonoacetaldehyde reductase
K12906 phpE; D-3-phosphoglycerate dehydrogenase
K12907 phpJ; aldehyde dehydrogenase
K12909 phpI; carboxyvinyl-carboxyphosphonate phosphorylmutase [EC:2.7.8.23 ]
K12911 phsA; phosphinothricin tripeptide synthetase PhsA
K12912 phsB; phosphinothricin tripeptide synthetase phsB [EC:6.2.1.67 ]
K12913 phsC; phosphinothricin tripeptide synthetase PhsC
K12915 dea; phosphinothricin tripeptide acetyl hydrolase
K20859 phnPP; phosphoribosyl 1,2-cyclic phosphate 1,2-diphosphodiesterase [EC:3.1.4.57 ]
K21196 phnZ; 2-amino-1-hydroxyethylphosphonate dioxygenase (glycine-forming) [EC:1.13.11.78 ]
K23996 phnY; methylphosphonate hydroxylase
K23999 fom1; phosphoenolpyruvate phosphomutase / 2-hydroxyethylphosphonate cytidylyltransferase
K25574 pntC; (2-aminoethyl)phosphonate cytidylyltransferase
K26913 pbfA; (R)-1-hydroxy-2-aminoethylphosphonate ammonia-lyase
K27877 pbfD; 2-(methylaminoethyl)phosphonate oxidase
K28018 pbfC; 2-(methylaminoethyl)phosphonate dehydrogenase (acceptor)
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
C22696 (1R)-(2-Amino-1-hydroxyethyl)phosphonate
Reference Authors Metcalf WW, van der Donk WA
Title Biosynthesis of phosphonic and phosphinic acid natural products.
Journal Reference Authors Xiao Y, Lee K, Liu P
Title Syntheses of the P-methylase substrates of the bialaphos biosynthetic pathway.
Journal Reference Authors van der Donk WA
Title Rings, radicals, and regeneration: the early years of a bioorganic laboratory.
Journal 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 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 Related ko00010 Glycolysis / Gluconeogenesis
ko00260 Glycine, serine and threonine metabolism
