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Proc Natl Acad Sci U S A

Title:		Isolation and determination of absolute configurations of insect-produced methyl-branched hydrocarbons
Author(s):		Bello JE; McElfresh JS; Millar JG;
Address:		"Departments of Chemistry and. Entomology, University of California, Riverside, CA 92521. Departments of Chemistry and Entomology, University of California, Riverside, CA 92521 jocelyn.millar@ucr.edu"
Journal Title:		Proc Natl Acad Sci U S A
Year:		2015
Volume:		20150112
Issue:		4
Page Number:		1077 - 1082
DOI:		10.1073/pnas.1417605112
ISSN/ISBN:		1091-6490 (Electronic) 0027-8424 (Print) 0027-8424 (Linking)
Abstract:		"Although the effects of stereochemistry have been studied extensively for volatile insect pheromones, little is known about the effects of chirality in the nonvolatile methyl-branched hydrocarbons (MBCHs) used by many insects as contact pheromones. MBCHs generally contain one or more chiral centers and so two or more stereoisomeric forms are possible for each structure. However, it is not known whether insects biosynthesize these molecules in high stereoisomeric purity, nor is it known whether insects can distinguish the different stereoisomeric forms of MBCHs. This knowledge gap is due in part to the lack of methods for isolating individual MBCHs from the complex cuticular hydrocarbon (CHC) blends of insects, as well as the difficulty in determining the absolute configurations of the isolated MBCHs. To address these deficiencies, we report a straightforward method for the isolation of individual cuticular hydrocarbons from the complex CHC blend. The method was used to isolate 36 pure MBCHs from 20 species in nine insect orders. The absolute stereochemistries of the purified MBCHs then were determined by digital polarimetry. The absolute configurations of all of the isolated MBCHs were determined to be (R) by comparison with a library of synthesized, enantiomerically pure standards, suggesting that the biosynthetic pathways used to construct MBCHs are highly conserved within the Insecta. The development of a straightforward method for isolation of specific CHCs will enable determination of their functional roles by providing pure compounds for bioassays"
Keywords:		Animals Heteroptera/*chemistry/metabolism Hydrocarbons/*chemistry/*isolation & purification/metabolism absolute configuration contact pheromone cuticular hydrocarbons isolation methyl-branched hydrocarbons;
Notes:		"MedlineBello, Jan E McElfresh, J Steven Millar, Jocelyn G eng Research Support, Non-U.S. Gov't Research Support, U.S. Gov't, Non-P.H.S. 2015/01/15 Proc Natl Acad Sci U S A. 2015 Jan 27; 112(4):1077-82. doi: 10.1073/pnas.1417605112. Epub 2015 Jan 12"