ISSN:
1573-1561
Keywords:
Insecta
;
Ceratitus capitata
;
medfly
;
trimedlure
;
enantiomer
;
attractant
;
lure
;
SAR
;
VdW
;
Chem-X
Source:
Springer Online Journal Archives 1860-2000
Topics:
Biology
,
Chemistry and Pharmacology
Notes:
Abstract tert-Butyl 4- (and 5-) chloro-trans-2-methylcyclohexane-1-carboxylate (TML), a mixture of four majortrans and four minorcis isomers, is used as an attractant for detecting and monitoring the male Mediterranean fruit fly (medfly),Ceratitis capitata (Wiedemann). The eight isomers (racemic mixtures) were isolated by HPLC, and their relative attractiveness in the field was determined. A quantitative structure-activity relationship (QSAR) was proposed that related a molecular measurement (Å3) of the TML structure to male medfly captures. More recently, thetrans-TML enantiomers were synthesized in sufficient quantities for field testing. This paper reports the computer-aided molecular modeling, via Chem-X, of thetrans-TML enantiomers and the staggered and superimposed fitting with the most attractive isomer, (1S,2S,4R)-TML-C, to determine common volumes and surface areas from Van der Waals (VdW) maps. Observations of structure-activity relationships (SAR) are reported for the staggered fittings.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1007/BF02033663
Permalink
