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MetaCyc Compound Class: a pyoverdine

Superclasses: a hydroxamatea hydroxamate siderophore
a secondary metabolitea siderophorea catecholate siderophore
a secondary metabolitea siderophorea hydroxamate siderophore
an alcohola diola benzenediola catechola catecholate siderophore
an aromatic compounda benzenediola catechola catecholate siderophore

Pyoverdines are a group of structurally related siderophores produced by fluorescent Pseudomonas species, in which they provide the primary iron uptake system.

Even though the structures of more than 50 different pyoverdines from different strains and species of Pseudomonas have been determined, they all possess similar structure composed of three parts: a conserved fluorescent dihydroxyquinoline chromophore, an acyl side chain (either dicarboxylic acid or amide) bound to the amino group of the chromophore (R1 in the structure below), and a variable peptide chain linked by an amide group bound to the C1 (rarely C3) carboxyl group of the chromophore (R2 in the structure below) [Visca07].

a pyoverdine compound structure

myristoylated pyoverdine intermediate,
pyoverdine biosynthetic intermediate,
pyoverdine I

SMILES: C([R1])CC(=O)NC2(=CC1(=CC(O)=C(O)C=C1N3(C2=NCCC3C(=O)N[R2])))

Reactions known to consume the compound:

Not in pathways:
a catechol + S-adenosyl-L-methionine → a guaiacol + S-adenosyl-L-homocysteine + H+

Not in pathways:
4 a benzenediol + oxygen → 4 a benzosemiquinone + 2 H2O

Reactions known to produce the compound:

ethylene biosynthesis III (microbes) , iron reduction and absorption :
an Fe(II)-siderophore + H+a siderophore + Fe2+

Not in pathways:
2 Fe2+ + 2 a siderophore + NADP+ + H+ ← 2 an Fe(III)-siderophore + NADPH

β-D-glucuronide and D-glucuronate degradation :
a β-D-glucuronoside + H2O → D-glucopyranuronate + an alcohol

glycerophosphodiester degradation :
a glycerophosphodiester + H2O → an alcohol + sn-glycerol 3-phosphate + H+

phosphate acquisition :
a phosphate monoester + H2O → an alcohol + phosphate

Not in pathways:
an organic hydroperoxide + NADH + H+an alcohol + NAD+ + H2O
a 6-phospho-β-D-galactoside + H2O → D-galactopyranose 6-phosphate + an alcohol
an α-D-glucuronoside + H2O → D-glucopyranuronate + an alcohol
an α amino acid ester + H2O → an alcohol + an α amino acid + H+
a phosphate monoester + H2O → an alcohol + phosphate
RH + a reduced [NADPH-hemoprotein reductase] + oxygen → ROH + an oxidized [NADPH-hemoprotein reductase] + H2O
an oligosaccharide with β-L-arabinopyranose at the non-reducing end + H2O → β-L-arabinopyranose + an alcohol
an N-acetyl-β-D-hexosaminide + H2O → an N-acetyl-β-D-hexosamine + an alcohol
a carboxylic ester + H2O → an alcohol + a carboxylate + H+
an acetic ester + H2O → an alcohol + acetate + H+
a reduced thioredoxin + an organic hydroperoxide → an oxidized thioredoxin + an alcohol + H2O
a 6-O-(β-D-xylopyranosyl)-β-D-glucopyranoside + H2O → primeverose + an alcohol
an organic molecule + H2O + 2 oxygen → an alcohol + 2 superoxide + 2 H+
an N5-acyl-L-ornithine-ester + H2O → an N5-acyl-L-ornithine + an alcohol
α-L-fucoside + H2O → L-fucopyranose + an alcohol
a 2-deoxy-α-D-glucoside + H2O → 2-deoxy-D-glucose + an alcohol

In Reactions of unknown directionality:

Not in pathways:
an alcohol + 3'-phosphoadenylyl-sulfate = adenosine 3',5'-bisphosphate + an organosulfate + H+
an alcohol + NAD(P)+ = an aldehyde + NAD(P)H + H+
an alcohol + NADP+ = an aldehyde + NADPH + H+
an alcohol + acetyl-CoA = an acetic ester + coenzyme A
trans-cinnamoyl-β-D-glucoside + an alcohol = alkyl cinnamate + D-glucopyranose
2 protein cysteines + an organic hydroperoxide = a protein disulfide + an alcohol + H2O
an organic molecule + an organic hydroperoxide = 2 an alcohol
an organic molecule + hydrogen peroxide = an alcohol + H2O

Enzymes activated by a pyoverdine, sorted by the type of activation, are:

Activator (Mechanism unknown) of: phosphoenolpyruvate carboxylase [Izui83]

Created 29-Dec-2009 by Caspi R, SRI International


Izui83: Izui K, Matsuda Y, Kameshita I, Katsuki H, Woods AE (1983). "Phosphoenolpyruvate carboxylase of Escherichia coli. Inhibition by various analogs and homologs of phosphoenolpyruvate." J Biochem (Tokyo) 1983;94(6);1789-95. PMID: 6368527

Visca07: Visca P, Imperi F, Lamont IL (2007). "Pyoverdine siderophores: from biogenesis to biosignificance." Trends Microbiol 15(1);22-30. PMID: 17118662

Report Errors or Provide Feedback
Please cite the following article in publications resulting from the use of MetaCyc: Caspi et al, Nucleic Acids Research 42:D459-D471 2014
Page generated by Pathway Tools version 19.5 (software by SRI International) on Tue May 3, 2016, biocyc13.