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Literature summary 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

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

Natural Substrates/ Products (Substrates)

EC Number Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
1.1.1.260 6-methylhept-5-en-2-one + NADH Thermoanaerobacter brockii sulcatone 6-methylhept-5-en-2-ol + NAD+ 100% enantiomeric excess for S(+)-sulcatol r
1.1.1.260 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
1.1.1.260 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
1.1.1.260 6-methylhept-5-en-2-one + NADH Saccharomyces cerevisiae sulcatone 6-methylhept-5-en-2-ol + NAD+ sulcatol r
1.1.1.260 6-methylhept-5-en-2-one + NADH Aspergillus niger sulcatone 6-methylhept-5-en-2-ol + NAD+ sulcatol r
1.1.1.260 6-methylhept-5-en-2-one + NADH Geotrichum candidum sulcatone 6-methylhept-5-en-2-ol + NAD+ sulcatol r
1.1.1.260 6-methylhept-5-en-2-one + NADH Clostridium tyrobutyricum sulcatone 6-methylhept-5-en-2-ol + NAD+ sulcatol r
1.1.1.260 6-methylhept-5-en-2-one + NADH Gnathotrichus sulcatus sulcatone 6-methylhept-5-en-2-ol + NAD+ sulcatol r
1.1.1.260 6-methylhept-5-en-2-one + NADH Gnathotrichus retusus sulcatone 6-methylhept-5-en-2-ol + NAD+ sulcatol r
1.1.1.260 6-methylhept-5-en-2-one + NADH Thermoanaerobacter brockii sulcatone 6-methylhept-5-en-2-ol + NAD+ sulcatol r
1.1.1.260 6-methylhept-5-en-2-one + NADH Saccharomyces cerevisiae sulcatone 6-methylhept-5-en-2-ol + NAD+ S enantiomer formed r
1.1.1.260 6-methylhept-5-en-2-one + NADH Thermoanaerobacter brockii sulcatone 6-methylhept-5-en-2-ol + NAD+ S enantiomer formed r
1.1.1.260 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
1.1.1.260 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
1.1.1.260 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

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

Source Tissue

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

Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
1.1.1.260 6-methylhept-5-en-2-one + NADH sulcatone Thermoanaerobacter brockii 6-methylhept-5-en-2-ol + NAD+ 100% enantiomeric excess for S(+)-sulcatol r
1.1.1.260 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
1.1.1.260 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
1.1.1.260 6-methylhept-5-en-2-one + NADH sulcatone Saccharomyces cerevisiae 6-methylhept-5-en-2-ol + NAD+ sulcatol r
1.1.1.260 6-methylhept-5-en-2-one + NADH sulcatone Aspergillus niger 6-methylhept-5-en-2-ol + NAD+ sulcatol r
1.1.1.260 6-methylhept-5-en-2-one + NADH sulcatone Geotrichum candidum 6-methylhept-5-en-2-ol + NAD+ sulcatol r
1.1.1.260 6-methylhept-5-en-2-one + NADH sulcatone Clostridium tyrobutyricum 6-methylhept-5-en-2-ol + NAD+ sulcatol r
1.1.1.260 6-methylhept-5-en-2-one + NADH sulcatone Gnathotrichus sulcatus 6-methylhept-5-en-2-ol + NAD+ sulcatol r
1.1.1.260 6-methylhept-5-en-2-one + NADH sulcatone Gnathotrichus retusus 6-methylhept-5-en-2-ol + NAD+ sulcatol r
1.1.1.260 6-methylhept-5-en-2-one + NADH sulcatone Thermoanaerobacter brockii 6-methylhept-5-en-2-ol + NAD+ sulcatol r
1.1.1.260 6-methylhept-5-en-2-one + NADH sulcatone Saccharomyces cerevisiae 6-methylhept-5-en-2-ol + NAD+ S enantiomer formed r
1.1.1.260 6-methylhept-5-en-2-one + NADH sulcatone Thermoanaerobacter brockii 6-methylhept-5-en-2-ol + NAD+ S enantiomer formed r
1.1.1.260 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
1.1.1.260 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
1.1.1.260 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

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