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Literature summary for 1.8.1.5 extracted from

  • Prussia, G.A.; Gauss, G.H.; Mus, F.; Conner, L.; DuBois, J.L.; Peters, J.W.
    Substitution of a conserved catalytic dyad into 2-KPCC causes loss of carboxylation activity (2016), FEBS Lett., 590, 2991-2996 .
    View publication on PubMed

Cloned(Commentary)

Cloned (Comment) Organism
recombinant expression of wild-type and mutant enzymes in Escherichia coli Xanthobacter autotrophicus

Protein Variants

Protein Variants Comment Organism
F501H/H506E site-directed mutagenesis of the catalytic dyad, substitution of the Phe-His active site residues by the canonical residues results in production of higher relative concentrations of acetone versus the natural product acetoacetate. Replacement of the His-Glu dyad from DSORs with Phe-His is critical for specifying carboxylation chemistry in enzyme 2-KPCC Xanthobacter autotrophicus

Natural Substrates/ Products (Substrates)

Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
2-(2-oxopropylthio)ethanesulfonate + CO2 + NADPH Xanthobacter autotrophicus
-
2-mercaptoethanesulfonate + acetoacetate + NADP+
-
?

Organism

Organism UniProt Comment Textmining
Xanthobacter autotrophicus Q56839
-
-

Reaction

Reaction Comment Organism Reaction ID
2-mercaptoethanesulfonate + acetoacetate + NADP+ = 2-(2-oxopropylthio)ethanesulfonate + CO2 + NADPH + H+ reaction mechanism for 2-KPCC begins with formation of enzyme-substrate disulfide adduct by the reduced form of the redox active disulfide. This step is followed by release of enolacetone anion intermediates for 2-KPCC. The primary catalytic fate of the enolacetone intermediate for the wild-type (Phe501) or variant (His501) 2-KPCC is acetoacetate or acetone, respectively Xanthobacter autotrophicus

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
2-(2-oxopropylthio)ethanesulfonate + CO2 + NADPH
-
Xanthobacter autotrophicus 2-mercaptoethanesulfonate + acetoacetate + NADP+
-
?

Synonyms

Synonyms Comment Organism
2-ketopropyl coenzyme M oxidoreductase/carboxylase
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Xanthobacter autotrophicus
2-KPCC
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Xanthobacter autotrophicus

Temperature Optimum [°C]

Temperature Optimum [°C] Temperature Optimum Maximum [°C] Comment Organism
30
-
assay at Xanthobacter autotrophicus

pH Optimum

pH Optimum Minimum pH Optimum Maximum Comment Organism
7.4
-
assay at Xanthobacter autotrophicus

Cofactor

Cofactor Comment Organism Structure
FAD
-
Xanthobacter autotrophicus
NADPH
-
Xanthobacter autotrophicus

General Information

General Information Comment Organism
evolution the enzyme belongs to the disulfide oxidoreductase (DSOR) family of enzymes. The characteristic His-Glu catalytic dyad of the DSOR family is replaced in 2-ketopropyl coenzyme M oxidoreductase/carboxylase (2-KPCC) uniquely by the residues Phe-His, potentially to eliminate proton-donating groups at a key position in the active site. These differences in 2-KPCC are key in discriminating between carbon dioxide and protons as attacking electrophiles Xanthobacter autotrophicus
physiological function 2-oxopropylcoenzyme M oxidoreductase/carboxylase (2-KPCC) catalyzes the reductive cleavage and carboxylation of 2-oxopropyl coenzyme M (2-KPC) to form acetoacetate and concomitantly regenerate CoM (2-mercaptoethanesulfonate) Xanthobacter autotrophicus