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IUBMB CommentsStudies on the effects of growth-stage and nutrient supply on the stereochemistry of sulcatone reduction in Clostridia pasteurianum, C. tyrobutyricum and Lactobacillus brevis suggest that there may be at least two sulcatone reductases with different stereospecificities.
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6-methylhept-5-en-2-one + NADH
6-methylhept-5-en-2-ol + NAD+
6-methylhept-5-en-2-one + NADH
6-methylhept-5-en-2-ol + NAD+
-
sulcatone
sulcatol, 80% sulcatol R(-) enantiomer after 24 h reaction time
r
6-methylhept-5-en-2-one + NADH
6-methylhept-5-en-2-ol + NAD+
-
enantiomeric selectivity substantially affected by pregrowth period and substrate concentration
sulcatol
r
6-methylhept-5-en-2-one + NADH
6-methylhept-5-en-2-ol + NAD+
-
sulcatone
sulcatol
r
6-methylhept-5-en-2-one + NADH
6-methylhept-5-en-2-ol + NAD+
-
sulcatone
sulcatol
r
6-methylhept-5-en-2-one + NADH
6-methylhept-5-en-2-ol + NAD+
-
sulcatone
sulcatol, 80% of sulcatol R enantiomer after 48 h reaction time
r
6-methylhept-5-en-2-one + NADH
6-methylhept-5-en-2-ol + NAD+
-
sulcatone
sulcatol
r
6-methylhept-5-en-2-one + NADH
6-methylhept-5-en-2-ol + NAD+
-
sulcatone
96% sulcatol R enantiomer after 17 h reaction time, sulcatol
r
6-methylhept-5-en-2-one + NADH
6-methylhept-5-en-2-ol + NAD+
-
sulcatone
only sensitive to S enantiomer, inhibited by the R enantiomer, sulcatol
r
6-methylhept-5-en-2-one + NADH
6-methylhept-5-en-2-ol + NAD+
-
sulcatone
sulcatol, mixture of 65% S(+)- and 35% S(-)-sulcatol isomers
r
6-methylhept-5-en-2-one + NADH
6-methylhept-5-en-2-ol + NAD+
-
sulcatone
sulcatol
r
6-methylhept-5-en-2-one + NADH
6-methylhept-5-en-2-ol + NAD+
-
R(-)-sulcatol in high enantiomeric excess formed irrespective of pregrowth period and substrate concentration
sulcatol
r
6-methylhept-5-en-2-one + NADH
6-methylhept-5-en-2-ol + NAD+
-
sulcatone
sulcatol, S enantiomer formed
r
6-methylhept-5-en-2-one + NADH
6-methylhept-5-en-2-ol + NAD+
-
sulcatone
100% enantiomeric excess for S(+)-sulcatol, sulcatol, S enantiomer formed
r
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6-methylhept-5-en-2-one + NADH
6-methylhept-5-en-2-ol + NAD+
6-methylhept-5-en-2-one + NADH
6-methylhept-5-en-2-ol + NAD+
-
sulcatone
sulcatol, 80% sulcatol R(-) enantiomer after 24 h reaction time
r
6-methylhept-5-en-2-one + NADH
6-methylhept-5-en-2-ol + NAD+
-
enantiomeric selectivity substantially affected by pregrowth period and substrate concentration
sulcatol
r
6-methylhept-5-en-2-one + NADH
6-methylhept-5-en-2-ol + NAD+
-
sulcatone
sulcatol
r
6-methylhept-5-en-2-one + NADH
6-methylhept-5-en-2-ol + NAD+
-
sulcatone
sulcatol
r
6-methylhept-5-en-2-one + NADH
6-methylhept-5-en-2-ol + NAD+
-
sulcatone
sulcatol, 80% of sulcatol R enantiomer after 48 h reaction time
r
6-methylhept-5-en-2-one + NADH
6-methylhept-5-en-2-ol + NAD+
-
sulcatone
sulcatol
r
6-methylhept-5-en-2-one + NADH
6-methylhept-5-en-2-ol + NAD+
-
sulcatone
96% sulcatol R enantiomer after 17 h reaction time, sulcatol
r
6-methylhept-5-en-2-one + NADH
6-methylhept-5-en-2-ol + NAD+
-
sulcatone
only sensitive to S enantiomer, inhibited by the R enantiomer, sulcatol
r
6-methylhept-5-en-2-one + NADH
6-methylhept-5-en-2-ol + NAD+
-
sulcatone
sulcatol, mixture of 65% S(+)- and 35% S(-)-sulcatol isomers
r
6-methylhept-5-en-2-one + NADH
6-methylhept-5-en-2-ol + NAD+
-
sulcatone
sulcatol
r
6-methylhept-5-en-2-one + NADH
6-methylhept-5-en-2-ol + NAD+
-
R(-)-sulcatol in high enantiomeric excess formed irrespective of pregrowth period and substrate concentration
sulcatol
r
6-methylhept-5-en-2-one + NADH
6-methylhept-5-en-2-ol + NAD+
-
sulcatone
sulcatol, S enantiomer formed
r
6-methylhept-5-en-2-one + NADH
6-methylhept-5-en-2-ol + NAD+
-
sulcatone
100% enantiomeric excess for S(+)-sulcatol, sulcatol, S enantiomer formed
r
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Tidswell, E.C.; Salter, G.J.; Kell, D.B.; Morris, J.G.
Enantioselectivity of sulcatone reduction by some anaerobic bacteria
Enzyme Microb. Technol.
21
143-147
1997
Clostridium tyrobutyricum, Levilactobacillus brevis
-
brenda
Tidswell, E.C.; Thompson, A.N.; Morris, J.G.
Selection in chemostat culture of a mutant strain of Clostridium tyrobutyricum improved in its reduction of ketones
Appl. Microbiol. Biotechnol.
35
317-322
1991
Clostridium tyrobutyricum, Clostridium tyrobutyricum PON5
brenda
Belan, A.; Bolte, J.; Fauve, A.; Gourcy, J.G.; Veschambre, H.
Use of biological systems for the preparation of chiral molecules. 3. An application in pheromone synthesis: Preparation of sulcatol enantiomers
J. Org. Chem.
52
256-260
1987
Aspergillus niger, Saccharomyces cerevisiae, Thermoanaerobacter brockii, Clostridium tyrobutyricum, Geotrichum candidum, Gnathotrichus retusus, Gnathotrichus sulcatus
-
brenda
BRENDA home
History
Enzyme Nomenclature
1.1.1.260 sulcatone reductase
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