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 acids
Pathway map rn00440 Phosphonate and phosphinate metabolism
Ortholog table Other DBs Reaction R00318 phosphonoacetate phosphonohydrolase
R00661 phosphoenolpyruvate 2,3-phosphonomutase
R00747 2-phosphonoacetaldehyde phosphonohydrolase
R02590 CTP:choline-phosphate cytidylyltransferase
R04053 3-phosphonopyruvate carboxy-lyase
R04152 (2-aminoethyl)phosphonate:pyruvate aminotransferase
R04247 CTP:ethanolamine-phosphate cytidylyltransferase
R04251 phosphonoacetaldehyde:NAD+ oxidoreductase
R04920 CMP-2-aminoethylphosphonate:1,2-diacylglycerol (2-aminoethylphosphonyl)transferase
R04922 CMP-N-trimethyl-2-aminoethylphosphonate:1,2-diacylglycerol (N-trimethyl-2-aminoethylphosphonyl)transferase
R05165 1-carboxyvinyl carboxyphosphonate phosphorylmutase (decarboxylating)
R08864 2-hydroxyethylphosphonate:O2 1,2-oxidoreductase (hydroxymethylphosphonate forming)
R08867 CTP:phosphonoformate cytidylyltransferase
R08870 acetyl-CoA:phosphinopyruvate C-acetyltransferase (thioester-hydrolysing, carboxymethyl forming)
R08871 acetyl-CoA:demethylphosphinothricin N-acetyltransferase
R08872 N-acetyldemethylphosphinothricin:L-alanine:L-alanine ligase (AMP-forming)
R08873 methylcobalamin:N-acetyldemethylphosphinothricin P-methyltransferase
R08874 N-acetylphosphinothricin amidohydrolase
R08875 methylcobalamin:N-acetyldemethylphosphinothricin-tripeptide P-methyltransferase
R08876 N-acetylbialaphos amidohydrolase
R08938 acetyl-CoA:phosphinothricin N-acetyltransferase
R09478 2-hydroxyethylphosphonate:NAD+ oxidoreductase
R10185 ATP:methylphosphonate 5-triphosphoribosyltransferase
R10186 alpha-D-ribose-1-methylphosphonate-5-triphosphate diphosphohydrolase
R10191 2-hydroxyethylphosphonate:O2 1,2-oxidoreductase (methylphosphonate forming)
R10204 alpha-D-ribose-1-methylphosphonate-5-phosphate C-P-lyase (methane forming)
R10205 5-phospho-alpha-D-ribose 1,2-cyclic phosphate 2-phosphohydrolase (alpha-D-ribose 1,5-bisphosphate-forming)
R10722 2-amino-1-hydroxyethylphosphonate:oxygen 1-oxidoreductase (glycine-forming)
R10724 (2-aminoethyl)phosphonate,2-oxoglutarate:oxygen oxidoreductase (1-hydroxylating)
R10972 5-phospho-alpha-D-ribose 1,2-cyclic phosphate 1-phosphohydrolase (D-ribose 2,5-bisphosphate-forming)
R10973 D-ribose-2,5-bisphosphate 2-phosphohydrolase
R11408 2-phosphinomethylmalate hydro-lyase [3-phosphinomethylmalate-forming]
R11479 acetyl-CoA:2-aminoethylphosphonate N-acetyltransferase
R11708 acetyl-CoA:3-phosphonopyruvate C-acetyltransferase
R12451 (hydroxymethyl)phosphonate:oxygen 1-oxidoreductase (formate-forming)
R12452 methylphosphonate,2-oxoglutarate:oxygen oxidoreductase (1-hydroxylating)
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
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 rn00010 Glycolysis / Gluconeogenesis
rn00260 Glycine, serine and threonine metabolism
KO pathway
