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Information on EC 3.1.1.57 - 2-pyrone-4,6-dicarboxylate lactonase and Organism(s) Sphingobium sp. and UniProt Accession O87170

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EC Tree
     3 Hydrolases
         3.1 Acting on ester bonds
             3.1.1 Carboxylic-ester hydrolases
                3.1.1.57 2-pyrone-4,6-dicarboxylate lactonase
IUBMB Comments
The product is most likely the keto-form of 4-oxalomesaconate (as shown in the reaction) [1,2]. It can be converted to the enol-form, 4-hydroxybuta-1,3-diene-1,2,4-trioate, either spontaneously or by EC 5.3.2.8, 4-oxalomesaconate tautomerase .
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Sphingobium sp.
UNIPROT: O87170
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Word Map
The taxonomic range for the selected organisms is: Sphingobium sp.
The expected taxonomic range for this enzyme is: Bacteria, Eukaryota
Synonyms
2-pyrone-4,6-dicarboxylate hydrolase, 2-pyrone-4,6-dicarboxylate lactonase, pdc hydrolase, more
SYNONYM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
hydrolysis of carboxylic ester
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SYSTEMATIC NAME
IUBMB Comments
2-pyrone-4,6-dicarboxylate lactonohydrolase
The product is most likely the keto-form of 4-oxalomesaconate (as shown in the reaction) [1,2]. It can be converted to the enol-form, 4-hydroxybuta-1,3-diene-1,2,4-trioate, either spontaneously or by EC 5.3.2.8, 4-oxalomesaconate tautomerase [3].
CAS REGISTRY NUMBER
COMMENTARY hide
84177-55-9
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SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
2-oxo-2H-pyran-4,6-dicarboxylate + H2O
(1E)-4-oxobut-1-ene-1,2,4-tricarboxylate
show the reaction diagram
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additional information
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the catalytic reaction contains the nucleophilic attack, the cleavage of C-O bond of lactone (substrate) and the intramolecular proton transfer. The intermediate has two intramolecular proton transfer pathways, leading to two final hydrolysis products. According to the energy profile, 4-carboxy-2-hydroxymuconate is the main hydrolysis product, and the isomerization between 4-carboxy-2-hydroxymuconate and 4-oxalomesaconate is suggested to occur in solvent. Residue Asp248 acts as a general base to activate the hydrolytic water molecule. Residues His31, His33 and His180 play assistant roles
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ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
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UniProt
Manually annotated by BRENDA team
REF.
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
Zhang, S.; Ma, G.; Liu, Y.; Ling, B.
Theoretical study of the hydrolysis mechanism of 2-pyrone-4,6-dicarboxylate (PDC) catalyzed by LigI
J. Mol. Graph. Model.
61
21-29
2015
Sphingobium sp. (O87170), Sphingobium sp. NBRC 103272 (O87170)
Manually annotated by BRENDA team