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MetaCyc Compound: β-D-galacturonate

Synonyms: β-D-galacturonic acid

Superclasses: all carbohydrates a carbohydrate a glycan D-galacturonate D-galactopyranuronate
an acid all carboxy acids a carboxylate a monocarboxylate a uronate a hexuronate galacturonate D-galacturonate D-galactopyranuronate

Chemical Formula: C6H9O7

Molecular Weight: 193.13 Daltons

Monoisotopic Molecular Weight: 194.0426526757 Daltons

β-D-galacturonate compound structure

SMILES: C(C1(C(C(C(C(O1)O)O)O)O))([O-])=O

InChI: InChI=1S/C6H10O7/c7-1-2(8)4(5(10)11)13-6(12)3(1)9/h1-4,6-9,12H,(H,10,11)/p-1/t1-,2+,3+,4-,6+/m0/s1

InChIKey: InChIKey=AEMOLEFTQBMNLQ-DTEWXJGMSA-M

Unification Links: ChEBI:85312 , ChemSpider:5360184 , PubChem:6992022

Standard Gibbs Free Energy of Change Formation (ΔfG in kcal/mol): -169.37196 Inferred by computational analysis [Latendresse13]

Reactions known to consume the compound:

D-galacturonate degradation II :
β-D-galacturonate + NAD+ → D-galactaro-1,5-lactone + NADH + H+

Not in pathways:
β-D-galacturonatealdehydo-D-galacturonate

UDP-D-galacturonate biosynthesis II (from D-galacturonate) :
D-galactopyranuronate + ATP → α-D-galacturonate 1-phosphate + ADP + H+

methyl ketone biosynthesis :
a carboxylate + ATP + coenzyme A → an acyl-CoA + AMP + diphosphate

Not in pathways:
an acyl-protein synthetase + a carboxylate + ATP → an acyl-protein thioester + AMP + diphosphate
a carboxylate + GTP + coenzyme A → an acyl-CoA + GDP + phosphate

Reactions known to produce the compound:

rhamnogalacturonan type I degradation I (fungi) :
α-D-galacturonate-[rhamnogalacturonan I oligosaccharide] + H2O → β-D-galacturonate + α-L-rhamnose-[rhamnogalacturonan I oligosaccharide]

L-ascorbate biosynthesis V :
α-D-galacturonate 1-phosphate + H2O → D-galactopyranuronate + phosphate

pectin degradation II :
α-D,α-D-digalacturonate → D-galactopyranuronate + 4-deoxy-L-threo-hex-4-enopyranuronate

pectin degradation III :
(1,4-α-D-galacturonide)n + H2O → D-galactopyranuronate + (1,4-α-D-galacturonide)(n-1)

3,3'-thiodipropanoate degradation :
3-sulfinopropionate + an acyl-CoA → 3-sulfinopropanoyl-CoA + a carboxylate

dimethylsulfoniopropanoate degradation II (cleavage) :
dimethylsulfoniopropanoate + an acyl-CoA → dimethylsulfoniopropioyl-CoA + a carboxylate

NAD/NADP-NADH/NADPH mitochondrial interconversion (yeast) :
an aldehyde + NADP+ + H2O → a carboxylate + NADPH + 2 H+
an aldehyde + NAD+ + H2O → a carboxylate + NADH + 2 H+

phosphatidylcholine resynthesis via glycerophosphocholine :
a phosphatidylcholine + 2 H2O → sn-glycero-3-phosphocholine + 2 a carboxylate + 2 H+

Not in pathways:
a 1-acyl 2-lyso-phosphatidylcholine[periplasmic space] + H2O[periplasmic space]a carboxylate[periplasmic space] + sn-glycero-3-phosphocholine[periplasmic space] + H+[periplasmic space]
an acyl-CoA + H2O → a carboxylate + coenzyme A + H+
an L-1-phosphatidyl-inositol + H2O → a 1-acyl-sn-glycero-3-phospho-D-myo-inositol + a carboxylate + H+
a carboxylic ester + H2O → an alcohol + a carboxylate + H+
an aldehyde + oxygen + H2O → a carboxylate + hydrogen peroxide + H+
an aldehyde + FMNH2 + oxygen → hν + a carboxylate + FMN + H2O + 2 H+
an acylcholine + H2O → choline + a carboxylate + H+
a β-monogalactosyldiacylglycerol + 2 H2O → 2 a carboxylate + 3-β-D-galactosyl-sn-glycerol + 2 H+
an acyl phosphate + H2O → a carboxylate + phosphate + H+
an S-acylglutathione + H2O → a carboxylate + glutathione
an N-acyl-L-aspartate + H2O → L-aspartate + a carboxylate

Reactions known to both consume and produce the compound:

D-galacturonate degradation III , L-ascorbate biosynthesis V , pectin degradation III , UDP-D-galacturonate biosynthesis II (from D-galacturonate) :
D-galactopyranuronatealdehydo-D-galacturonate

sphingolipid recycling and degradation (yeast) :
a dihydroceramide + H2O ↔ sphinganine + a carboxylate

In Reactions of unknown directionality:

Not in pathways:
a monocarboxylic acid amide + H2O = a monocarboxylate + ammonium

Not in pathways:
eugenol + a carboxylate + NADP+ = a coniferyl ester + NADPH
a 2-acyl 1-lyso-phosphatidylcholine[periplasmic space] + H2O[periplasmic space] = a carboxylate[periplasmic space] + sn-glycero-3-phosphocholine[periplasmic space] + H+[periplasmic space]
an aldehyde + an electron-transfer quinone + H2O = a carboxylate + an electron-transfer quinol + H+
a triacyl-sn-glycerol + H2O = a 1,2-diacyl-sn-glycerol + a carboxylate + H+
a penicillin + H2O = 6-aminopenicillanate + a carboxylate
an aldehyde[periplasmic space] + FAD[periplasmic space] + H2O[periplasmic space] = a carboxylate[periplasmic space] + FADH2[periplasmic space]
a nitrile + 2 H2O = a carboxylate + ammonium
an aliphatic nitrile + 2 H2O = a carboxylate + ammonium
an N-acyl-L-homoserine lactone + H2O = L-homoserine lactone + a carboxylate
an aldehyde + an oxidized unknown electron acceptor + H2O = a carboxylate + an reduced unknown electron acceptor + H+
an N-acylated aromatic-L-amino acid + H2O = a carboxylate + an aromatic L-amino acid
an N-acylated-D-amino acid + H2O = a D-amino acid + a carboxylate
an N-acylated aliphatic-L-amino acid + H2O = a carboxylate + an aliphatic L-amino acid
a D-hexose + an acyl phosphate = a D-hexose-phosphate + a carboxylate
an aldehyde + 2 an oxidized ferredoxin + H2O = a carboxylate + 2 a reduced ferredoxin + 3 H+
an aldehyde + NAD(P)+ + H2O = a carboxylate + NAD(P)H + 2 H+
an N-acyl-D-glutamate + H2O = a carboxylate + D-glutamate
an anilide + H2O = aniline + a carboxylate + H+
a 5'-acylphosphoadenosine + H2O = a carboxylate + AMP + 2 H+
a 3-acylpyruvate + H2O = a carboxylate + pyruvate + H+
an N6acyl-L-lysine + H2O = a carboxylate + L-lysine
an N-acyl-D-aspartate + H2O = a carboxylate + D-aspartate

In Transport reactions:
D-galacturonate[periplasmic space] + H+[periplasmic space]D-galacturonate[cytosol] + H+[cytosol]

Enzymes activated by β-D-galacturonate, sorted by the type of activation, are:

Activator (Mechanism unknown) of: D-mannonate dehydratase [RobertBaudouy73]

Enzymes inhibited by β-D-galacturonate, sorted by the type of inhibition, are:

Inhibitor (Competitive) of: rhamnogalacturonan exolyase [Ochiai07]

This compound has been characterized as an alternative substrate of the following enzymes: D-glucuronate dehydrogenase

Credits:
Created 28-Jul-2010 by Caspi R , SRI International


References

Latendresse13: Latendresse M. (2013). "Computing Gibbs Free Energy of Compounds and Reactions in MetaCyc."

Ochiai07: Ochiai A, Itoh T, Kawamata A, Hashimoto W, Murata K (2007). "Plant cell wall degradation by saprophytic Bacillus subtilis strains: gene clusters responsible for rhamnogalacturonan depolymerization." Appl Environ Microbiol 73(12);3803-13. PMID: 17449691

RobertBaudouy73: Robert-Baudouy JM, Stoeber FR (1973). "[Purification and properties of D-mannonate hydrolyase from Escherichia coli K12]." Biochim Biophys Acta 1973;309(2);473-85. PMID: 4581499


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 SRI International Pathway Tools version 19.0 on Fri Aug 28, 2015, BIOCYC14A.