Lipase-catalyzed kinetic resolution of 4-hydroxy-5-dodecynonitrile and its application to facile synthesis of a cupreous chafer beetle sex pheromone

Journal of Fermentation and Bioengineering

Volumn 86, Issue 5, 1998, Pages 508-509

  Fukusaki, Ei Ichiro ^a   Satoda, Shiro ^b   Senda, Shuji ^b   Omata, Tetsuo ^b  

^a OSAKA UNIVERSITY   (Japan)

^b NITTO DENKO CORPORATION   (Japan)

Author keywords

Cupreous chafer; Hydroxy nitrile; Lipase; Sex pheromone; Synthesis

Indexed keywords

ACYLATION; BIOSYNTHESIS; CATALYSIS; ENZYMES; NITROGEN COMPOUNDS; ORGANIC SOLVENTS; REACTION KINETICS;

ENANTIOSELECTIVE ACYLATION; HYDROXYDODECYNONITRILE; LIPASE; PHEROMONE;

HORMONES;

SEX PHEROMONE; TRIACYLGLYCEROL LIPASE;

ARTICLE; BEETLE; CATALYSIS; CHEMICAL REACTION; HORMONE SYNTHESIS; NONHUMAN;

ANOMALA CUPREA; COLEOPTERA;

EID: 0032446725     PISSN: 0922338X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0922-338X(98)80161-X     Document Type: Article

References (8)

1. Barton, D. and Ollis, W. D.: Nitrogen compounds, carboxylic acids, phosphorous compounds, p. 385-590. In Sutherland, I. O. (ed.), Comprehensive organic chemistry. Pergamon Press, Oxford (1979).
2. Itoh, T. and Takagi, Y.: Stereorecognition enhancement by the sulfur functional group in the lipase hydrolysis. An efficient synthesis of the optically active beta-hydroxy nitriles. Chemisty Lett., 1505-1506 (1989).
3. Itoh, T., Takagi, Y., and Nishiyama, S.: Enhanced enatioselectivity of an enzymatic reaction by the sulfur functional group. A simple preparation of optically active beta-hydroxy nitriles using a lipase. J. Org. Chem., 56, 1521-1524 (1991).
4. Takagi, Y. and Itoh, T.: Synthesis of optically active 4-hydroxyalkanenitriles via an enzymatic reaction. Bull. Chem. Soc. Jpn., 66, 2949-2953 (1993).
5. Leal, W. S.: (R,Z)-5-(-)-(Oct-1-enyl)oxacyclopentan-2-one, the sex pheromone of the scrab beetle, Anomala cuprea. Naturwissenschaften., 78, 521-523 (1991).
6. Fukusaki, E., Senda, S., Nakazono, Y., and Omata, T.: Synthesis of the enantiomers of (Z)-5-(1-octynyl)oxacyclopentan-2-one, a sex pheromone of the cupreous chafer beetle, Anomala cuprea Hope. Biosci. Biotech. Biochem., 56, 1160-1161 (1992).
7. Leal, W. S. and Mochizuki, F.: Sex pheromone reception in the scarab beetle Anomala cuprea: enantiomeric descrimination by sensislla placodea. Naturwissenschaften, 80, 278-281 (1993).
8. Leal, W. S., Sawada, M., and Hasegawa, M.: The scrab beetle Anomala cuprea utilize the sex pheromone of Popillia japonica as a minor component. J. Chem. Ecol., 19, 1303-1313 (1993).