ENTRY       gmx00440                    Pathway
NAME        Phosphonate and phosphinate metabolism - Glycine max (soybean)
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 gmx00440  Phosphonate and phosphinate metabolism
DBLINKS     GO: 0019634
ORGANISM    Glycine max (soybean) [GN:gmx]
GENE        100781961  ethanolamine-phosphate cytidylyltransferase [KO:K00967] [EC:2.7.7.14]
            100804449  ethanolamine-phosphate cytidylyltransferase isoform X1 [KO:K00967] [EC:2.7.7.14]
            100796401  ethanolamine-phosphate cytidylyltransferase [KO:K00967] [EC:2.7.7.14]
            100775240  ethanolamine-phosphate cytidylyltransferase [KO:K00967] [EC:2.7.7.14]
            100782910  choline/ethanolaminephosphotransferase 1 [KO:K00993] [EC:2.7.8.1]
            732642  AAPT1; aminoalcoholphosphotransferase [KO:K00993] [EC:2.7.8.1]
            100803699  choline-phosphate cytidylyltransferase 2 [KO:K00968] [EC:2.7.7.15]
            100786249  choline-phosphate cytidylyltransferase 1 isoform X1 [KO:K00968] [EC:2.7.7.15]
            100791886  uncharacterized protein LOC100791886 [KO:K00968] [EC:2.7.7.15]
            100807840  choline-phosphate cytidylyltransferase B-like [KO:K00968] [EC:2.7.7.15]
            100790615  choline-phosphate cytidylyltransferase 2 [KO:K00968] [EC:2.7.7.15]
COMPOUND    C00022  Pyruvate
            C00033  Acetate
            C00037  Glycine
            C00058  Formate
            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
            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
REFERENCE   PMID:19489722
  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   PMID:19053721
  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   PMID:17168571
  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   PMID:15616300
  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   PMID:15574905
  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
REL_PATHWAY gmx00010  Glycolysis / Gluconeogenesis
            gmx00030  Pentose phosphate pathway
            gmx00260  Glycine, serine and threonine metabolism
KO_PATHWAY  ko00440
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