In:
Journal of Mass Spectrometry, Wiley, Vol. 38, No. 3 ( 2003-03), p. 328-332
Abstract:
The utility of liquid chromatography combined with time‐of‐flight mass spectrometry (LC/TOFMS) was demonstrated for studies on chiral unsaturated epoxy compounds, sex pheromones produced mainly by female moths in the family Geometridae. By electrospray ionization (ESI), each synthetic epoxyalkadiene derived from ( Z , Z , Z )‐3,6,9‐triene with a C 18 –C 23 straight chain showed three ion series, [M + NH 4 ] + , [M + H] + and [M − OH] + , with high resolution and good sensitivity, indicating its molecular formula. In addition to these, characteristic fragment ions at m / z M − 57 and M − 71 for the 3,4‐epoxides and at m / z M − 123 and 123 for the 9,10‐epoxides were detected, whereas the 6,7‐epoxides did not produce fragment ions that reflected their structures. Monitoring these diagnostic ions during the LC/MS analysis of a gland extract, the natural sex pheromone of the mulberry looper was confirmed to be ( Z , Z )‐ cis ‐9,10‐epoxy‐3,6‐octadecadiene, which was separable from the other positional isomers on an ODS column. Furthermore, ( Z , Z )‐ cis ‐3,4‐epoxy‐6,9‐nonadecadiene secreted by the Japanese giant looper was analyzed with a chiral column, and the stereochemistry was determined directly. Copyright © 2003 John Wiley & Sons, Ltd.
Type of Medium:
Online Resource
ISSN:
1076-5174
,
1096-9888
Language:
English
Publisher:
Wiley
Publication Date:
2003
detail.hit.zdb_id:
2197367-2
detail.hit.zdb_id:
1472468-6
detail.hit.zdb_id:
7414-7
SSG:
11
SSG:
12
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