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首页> 美国卫生研究院文献>Proceedings of the National Academy of Sciences of the United States of America >Isolation and determination of absolute configurations of insect-produced methyl-branched hydrocarbons
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Isolation and determination of absolute configurations of insect-produced methyl-branched hydrocarbons

机译：昆虫生产的甲基支链烃的绝对构型的分离和测定

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摘要

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.
机译：尽管已经对挥发性昆虫信息素进行了立体化学作用的广泛研究，但对于许多昆虫用作接触信息素的非挥发性甲基支链烃（MBCH）中的手性效应知之甚少。 MBCH通常包含一个或多个手性中心，因此每种结构可能有两种或多种立体异构形式。但是，不知道昆虫是否以高立体异构体纯度生物合成这些分子，也不知道昆虫是否可以区分MBCH的不同立体异构形式。这种知识鸿沟部分是由于缺乏从昆虫的复杂表皮碳氢化合物（CHC）混合物中分离单个MBCH的方法，以及难以确定分离的MBCH的绝对构型。为了解决这些不足，我们报告了一种从复杂的CHC混合物中分离单个表皮碳氢化合物的简单方法。该方法用于从九种昆虫的20种物种中分离出36种纯MBCH。然后通过数字极化测定法确定纯化的MBCH的绝对立体化学。通过与合成的对映体纯标准品库进行比较，确定所有分离的MBCH的绝对构型为（R），这表明用于构建MBCH的生物合成途径在昆虫纲中高度保守。分离特定CHC的简单方法的开发将通过提供用于生物测定的纯化合物来确定其功能作用。

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