KEGG PATHWAY: rn00440

PATHWAY: rn00440

Entry

rn00440                     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

Pathway map

rn00440

Phosphonate and phosphinate metabolism

Other DBs

GO:

0019634

Reaction

R00318

phosphonoacetate phosphonohydrolase

R00661

phosphoenolpyruvate 2,3-phosphonomutase

R00747

2-phosphonoacetaldehyde phosphonohydrolase

R02590

CTP:choline-phosphate cytidylyltransferase

R02592

R04051

R04053

3-phosphonopyruvate carboxy-lyase

R04152

(2-aminoethyl)phosphonate:pyruvate aminotransferase

R04247

CTP:ethanolamine-phosphate cytidylyltransferase

R04250

R04251

phosphonoacetaldehyde:NAD+ oxidoreductase

R04252

R04920

CMP-2-aminoethylphosphonate:1,2-diacylglycerol (2-aminoethylphosphonyl)transferase

R04921

R04922

CMP-N-trimethyl-2-aminoethylphosphonate:1,2-diacylglycerol (N-trimethyl-2-aminoethylphosphonyl)transferase

R04923

R04924

R04925

R05165

1-carboxyvinyl carboxyphosphonate phosphorylmutase (decarboxylating)

R08200

R08861

R08864

2-hydroxyethylphosphonate:O2 1,2-oxidoreductase (hydroxymethylphosphonate forming)

R08865

R08866

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)

R08874

N-acetylphosphinothricin amidohydrolase

R08876

N-acetylbialaphos amidohydrolase

R08877

R08881

R08882

R08883

R08884

R08885

R08886

R08887

R08888

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]; phosphinomethylmalate isomerase

R11479

acetyl-CoA:2-aminoethylphosphonate N-acetyltransferase

R11480

R11481

R11708

acetyl-CoA:3-phosphonopyruvate C-acetyltransferase

R12451

(hydroxymethyl)phosphonate:oxygen 1-oxidoreductase (formate-forming)

R12452

methylphosphonate,2-oxoglutarate:oxygen oxidoreductase (1-hydroxylating)

R13195

(1R)-(2-amino-1-hydroxyethyl)phosphonate ammonia-lyase

R13384

2-(methylaminoethyl)phosphonate oxidase:oxygen oxidoreductase (phosphonoacetaldehyde-forming)

R13389

2-Aminoethylphosphonate oxidase:oxygen oxidoreductase (phosphonoacetaldehyde-forming)

R13411

S-adenosyl-L-methionine:N-acetyldemethylphosphinothricin P-methyltransferase

R13413

S-adenosyl-L-methionine:N-acetyldemethylphosphinothricin-tripeptide P-methyltransferase

R13438

2-(methylaminoethyl)phosphonate:acceptor oxidoreductase (phosphonoacetaldehyde-forming)

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

C22696

(1R)-(2-Amino-1-hydroxyethyl)phosphonate

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

Related
pathway

rn00010