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Literature summary extracted from

  • Loschonsky, S.; Waltzer, S.; Brecht, V.; Mueller, M.
    Elucidation of the enantioselective cyclohexane-1,2-dione hydrolase catalyzed formation of (S)-acetoin (2014), ChemCatChem, 6, 969-972.
No PubMed abstract available

Application

EC Number Application Comment Organism
3.7.1.11 synthesis the enzyme can be used to obtain highly enantioenriched products Azoarcus sp.

Metals/Ions

EC Number Metals/Ions Comment Organism Structure
2.2.1.6 Mg2+ required Azoarcus sp.

Natural Substrates/ Products (Substrates)

EC Number Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
3.7.1.11 cyclohexane-1,2-dione + H2O Azoarcus sp.
-
 6-oxohexanoate
-
 ?
3.7.1.11 cyclohexane-1,2-dione + H2O Azoarcus sp. 22Lin
-
 6-oxohexanoate
-
 ?

Organism

EC Number Organism UniProt Comment Textmining
2.2.1.6 Azoarcus sp.
-
-
-
2.2.1.6 Azoarcus sp. 22Lin
-
-
-
3.7.1.11 Azoarcus sp.
-
-
-
3.7.1.11 Azoarcus sp. 22Lin
-
-
-

Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
2.2.1.6 2 pyruvate enzymatic formation of highly enantioenriched acetoin from two molecules of pyruvate occurs without the release of acetaldehyde or acetolactate Azoarcus sp. (S)-acetoin + 2 CO2 87-90%ee ?
2.2.1.6 2 pyruvate enzymatic formation of highly enantioenriched acetoin from two molecules of pyruvate occurs without the release of acetaldehyde or acetolactate Azoarcus sp. 22Lin (S)-acetoin + 2 CO2 87-90%ee ?
2.2.1.6 additional information ThDP-dependent cyclohexane-1,2-dione hydrolase (CDH) is able to form (S)-acetoin with particularly high enantioselectivity (up to 95%ee) by all three possible pathways: homocoupling of pyruvate, homocoupling of acetaldehyde, or cross-coupling of acetaldehyde (as acceptor) and pyruvate (as donor), high enantioselectivity in the CDH-catalyzed formation of (S)-acetoin. An unprecedented non-acetolactate pathway for the homocoupling of pyruvate explains the high enantioselectivity in the CDH-catalyzed formation of (S)-acetoin, enzymatic formation of highly enantioenriched acetoin from two molecules of pyruvate occurs without the release of acetaldehyde or acetolactate, competition assay, mechanism, overview Azoarcus sp. ?
-
 ?
2.2.1.6 additional information ThDP-dependent cyclohexane-1,2-dione hydrolase (CDH) is able to form (S)-acetoin with particularly high enantioselectivity (up to 95%ee) by all three possible pathways: homocoupling of pyruvate, homocoupling of acetaldehyde, or cross-coupling of acetaldehyde (as acceptor) and pyruvate (as donor), high enantioselectivity in the CDH-catalyzed formation of (S)-acetoin. An unprecedented non-acetolactate pathway for the homocoupling of pyruvate explains the high enantioselectivity in the CDH-catalyzed formation of (S)-acetoin, enzymatic formation of highly enantioenriched acetoin from two molecules of pyruvate occurs without the release of acetaldehyde or acetolactate, competition assay, mechanism, overview Azoarcus sp. 22Lin ?
-
 ?
3.7.1.11 cyclohexane-1,2-dione + H2O
-
 Azoarcus sp. 6-oxohexanoate
-
 ?
3.7.1.11 cyclohexane-1,2-dione + H2O
-
 Azoarcus sp. 22Lin 6-oxohexanoate
-
 ?
3.7.1.11 additional information the enzme catalyze asymmetric CC bond formation from pyruvate (as donor) and an aldehyde (as acceptor). Thiamine diphosphate-dependent enzymes catalyze the formation of acetoin (3-hydroxybutan-2-one) through one of three different pathways: homocoupling of pyruvate, homocoupling of acetaldehyde, or cross-coupling of acetaldehyde (as acceptor) and pyruvate (as donor). Thiamine diphosphate-dependent cyclohexane-1,2-dione hydrolase is able to form (S)-acetoin with particularly high enantioselectivity (up to 95%ee) by all three pathways. An unprecedented non-acetolactate pathway for the homocoupling of pyruvate explains the high enantioselectivity in the CDH-catalyzed formation of (S)-acetoin, enzymatic formation of highly enantioenriched acetoin from two molecules of pyruvate occurs without the release of acetaldehyde or acetolactate, mechanism, overview Azoarcus sp. ?
-
 ?
3.7.1.11 additional information the enzme catalyze asymmetric CC bond formation from pyruvate (as donor) and an aldehyde (as acceptor). Thiamine diphosphate-dependent enzymes catalyze the formation of acetoin (3-hydroxybutan-2-one) through one of three different pathways: homocoupling of pyruvate, homocoupling of acetaldehyde, or cross-coupling of acetaldehyde (as acceptor) and pyruvate (as donor). Thiamine diphosphate-dependent cyclohexane-1,2-dione hydrolase is able to form (S)-acetoin with particularly high enantioselectivity (up to 95%ee) by all three pathways. An unprecedented non-acetolactate pathway for the homocoupling of pyruvate explains the high enantioselectivity in the CDH-catalyzed formation of (S)-acetoin, enzymatic formation of highly enantioenriched acetoin from two molecules of pyruvate occurs without the release of acetaldehyde or acetolactate, mechanism, overview Azoarcus sp. 22Lin ?
-
 ?

Synonyms

EC Number Synonyms Comment Organism
3.7.1.11 Cdh
-
 Azoarcus sp.

Temperature Optimum [°C]

EC Number Temperature Optimum [°C] Temperature Optimum Maximum [°C] Comment Organism
2.2.1.6 30
-
 assay at Azoarcus sp.
3.7.1.11 30
-
 assay at Azoarcus sp.

pH Optimum

EC Number pH Optimum Minimum pH Optimum Maximum Comment Organism
2.2.1.6 6.5
-
 assay at Azoarcus sp.
3.7.1.11 6.5
-
 assay at Azoarcus sp.

Cofactor

EC Number Cofactor Comment Organism Structure
2.2.1.6 FAD one molecule per enzyme molecule Azoarcus sp.
2.2.1.6 thiamine diphosphate dependent on, one molecule per enzyme molecule Azoarcus sp.
3.7.1.11 thiamine diphosphate dependent on Azoarcus sp.