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Literature summary for 1.1.1.260 extracted from

  • 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 (1987), J. Org. Chem., 52, 256-260.
No PubMed abstract available

Application

Application Comment Organism
synthesis preparation of sulcatol enantiomers Saccharomyces cerevisiae
synthesis preparation of sulcatol enantiomers Aspergillus niger
synthesis preparation of sulcatol enantiomers Geotrichum candidum
synthesis preparation of sulcatol enantiomers Clostridium tyrobutyricum
synthesis preparation of sulcatol enantiomers Gnathotrichus sulcatus
synthesis preparation of sulcatol enantiomers Gnathotrichus retusus
synthesis preparation of sulcatol enantiomers Thermoanaerobacter brockii

Natural Substrates/ Products (Substrates)

Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
6-methylhept-5-en-2-one + NADH Thermoanaerobacter brockii sulcatone 6-methylhept-5-en-2-ol + NAD+ 100% enantiomeric excess for S(+)-sulcatol r
6-methylhept-5-en-2-one + NADH Geotrichum candidum sulcatone 6-methylhept-5-en-2-ol + NAD+ 96% sulcatol R enantiomer after 17 h reaction time r
6-methylhept-5-en-2-one + NADH Gnathotrichus retusus sulcatone 6-methylhept-5-en-2-ol + NAD+ only sensitive to S enantiomer, inhibited by the R enantiomer r
6-methylhept-5-en-2-one + NADH Saccharomyces cerevisiae sulcatone 6-methylhept-5-en-2-ol + NAD+ sulcatol r
6-methylhept-5-en-2-one + NADH Aspergillus niger sulcatone 6-methylhept-5-en-2-ol + NAD+ sulcatol r
6-methylhept-5-en-2-one + NADH Geotrichum candidum sulcatone 6-methylhept-5-en-2-ol + NAD+ sulcatol r
6-methylhept-5-en-2-one + NADH Clostridium tyrobutyricum sulcatone 6-methylhept-5-en-2-ol + NAD+ sulcatol r
6-methylhept-5-en-2-one + NADH Gnathotrichus sulcatus sulcatone 6-methylhept-5-en-2-ol + NAD+ sulcatol r
6-methylhept-5-en-2-one + NADH Gnathotrichus retusus sulcatone 6-methylhept-5-en-2-ol + NAD+ sulcatol r
6-methylhept-5-en-2-one + NADH Thermoanaerobacter brockii sulcatone 6-methylhept-5-en-2-ol + NAD+ sulcatol r
6-methylhept-5-en-2-one + NADH Saccharomyces cerevisiae sulcatone 6-methylhept-5-en-2-ol + NAD+ S enantiomer formed r
6-methylhept-5-en-2-one + NADH Thermoanaerobacter brockii sulcatone 6-methylhept-5-en-2-ol + NAD+ S enantiomer formed r
6-methylhept-5-en-2-one + NADH Gnathotrichus sulcatus sulcatone 6-methylhept-5-en-2-ol + NAD+ mixture of 65% S(+)- and 35% S(-)-sulcatol isomers r
6-methylhept-5-en-2-one + NADH Clostridium tyrobutyricum sulcatone 6-methylhept-5-en-2-ol + NAD+ 80% of sulcatol R enantiomer after 48 h reaction time r
6-methylhept-5-en-2-one + NADH Aspergillus niger sulcatone 6-methylhept-5-en-2-ol + NAD+ 80% sulcatol R(-) enantiomer after 24 h reaction time r

Organism

Organism UniProt Comment Textmining
Aspergillus niger
-
-
-
Clostridium tyrobutyricum
-
-
-
Geotrichum candidum
-
-
-
Gnathotrichus retusus
-
-
-
Gnathotrichus sulcatus
-
-
-
Saccharomyces cerevisiae
-
-
-
Thermoanaerobacter brockii
-
-
-

Source Tissue

Source Tissue Comment Organism Textmining
cell culture
-
Saccharomyces cerevisiae
-
cell culture
-
Aspergillus niger
-
cell culture
-
Geotrichum candidum
-
cell culture
-
Clostridium tyrobutyricum
-
cell culture
-
Gnathotrichus sulcatus
-
cell culture
-
Gnathotrichus retusus
-
cell culture
-
Thermoanaerobacter brockii
-

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
6-methylhept-5-en-2-one + NADH sulcatone Thermoanaerobacter brockii 6-methylhept-5-en-2-ol + NAD+ 100% enantiomeric excess for S(+)-sulcatol r
6-methylhept-5-en-2-one + NADH sulcatone Geotrichum candidum 6-methylhept-5-en-2-ol + NAD+ 96% sulcatol R enantiomer after 17 h reaction time r
6-methylhept-5-en-2-one + NADH sulcatone Gnathotrichus retusus 6-methylhept-5-en-2-ol + NAD+ only sensitive to S enantiomer, inhibited by the R enantiomer r
6-methylhept-5-en-2-one + NADH sulcatone Saccharomyces cerevisiae 6-methylhept-5-en-2-ol + NAD+ sulcatol r
6-methylhept-5-en-2-one + NADH sulcatone Aspergillus niger 6-methylhept-5-en-2-ol + NAD+ sulcatol r
6-methylhept-5-en-2-one + NADH sulcatone Geotrichum candidum 6-methylhept-5-en-2-ol + NAD+ sulcatol r
6-methylhept-5-en-2-one + NADH sulcatone Clostridium tyrobutyricum 6-methylhept-5-en-2-ol + NAD+ sulcatol r
6-methylhept-5-en-2-one + NADH sulcatone Gnathotrichus sulcatus 6-methylhept-5-en-2-ol + NAD+ sulcatol r
6-methylhept-5-en-2-one + NADH sulcatone Gnathotrichus retusus 6-methylhept-5-en-2-ol + NAD+ sulcatol r
6-methylhept-5-en-2-one + NADH sulcatone Thermoanaerobacter brockii 6-methylhept-5-en-2-ol + NAD+ sulcatol r
6-methylhept-5-en-2-one + NADH sulcatone Saccharomyces cerevisiae 6-methylhept-5-en-2-ol + NAD+ S enantiomer formed r
6-methylhept-5-en-2-one + NADH sulcatone Thermoanaerobacter brockii 6-methylhept-5-en-2-ol + NAD+ S enantiomer formed r
6-methylhept-5-en-2-one + NADH sulcatone Gnathotrichus sulcatus 6-methylhept-5-en-2-ol + NAD+ mixture of 65% S(+)- and 35% S(-)-sulcatol isomers r
6-methylhept-5-en-2-one + NADH sulcatone Clostridium tyrobutyricum 6-methylhept-5-en-2-ol + NAD+ 80% of sulcatol R enantiomer after 48 h reaction time r
6-methylhept-5-en-2-one + NADH sulcatone Aspergillus niger 6-methylhept-5-en-2-ol + NAD+ 80% sulcatol R(-) enantiomer after 24 h reaction time r

Cofactor

Cofactor Comment Organism Structure
NADH
-
Saccharomyces cerevisiae
NADH
-
Aspergillus niger
NADH
-
Geotrichum candidum
NADH
-
Clostridium tyrobutyricum
NADH
-
Gnathotrichus sulcatus
NADH
-
Gnathotrichus retusus
NADH
-
Thermoanaerobacter brockii
NADPH
-
Clostridium tyrobutyricum
NADPH
-
Thermoanaerobacter brockii