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Nature:研究简化前列腺素合成过程

来源:新华社 2012-08-21 16:57

前列腺素是一类化学物质的总称,它们可用于制造治疗青光眼等疾病的药物。据介绍,一些基于前列腺素的药物每年销售额超过10亿美元。目前各家药厂仍沿用1969年由伊莱亚斯·科里发明的方法来合成前列腺素,科里曾因相关发明获得诺贝尔化学奖,这套方法需要20个步骤才能最终合成前列腺素。

据研究人员介绍,通过使用一种有机催化剂,可以将合成前列腺素的步骤数减少到7个,这将有助降低工业上生产相关药物的成本。

领导这次研究的阿加沃尔教授说,虽然过去合成前列腺素的方法费时费事,但由于医疗上的需要,人们还是不得不用这套方法来合成前列腺素,现在有了更简单的合成方法后,基于前列腺素的相关药物成本有望降低,可以让更多人用得起这类药物。(生物谷Bioon.com)

Stereocontrolled organocatalytic synthesis of prostaglandin PGF2α in seven steps

Graeme Coulthard, William Erb & Varinder K. Aggarwal

Prostaglandins are hormone-like chemical messengers that regulate a broad range of physiological activities, including blood circulation, digestion and reproduction. Their biological activities and their complex molecular architectures have made prostaglandins popular targets for synthetic organic chemists for over 40 years. Prostaglandin analogues are widely used as pharmaceuticals and some, such as latanoprost, which is used to treat glaucoma, have become billion-dollar drugs. Previously reported syntheses of these compounds are quite lengthy, and every chemical step costs time and energy, generates waste and is accompanied by material losses. Using a new bond disconnection, here we report a concise synthesis of the most complex prostaglandin, PGF2α, with high levels of control of relative and absolute stereochemistry, and fewer steps. The key step is an aldol cascade reaction of succinaldehyde using proline organocatalysis to create a bicyclic enal in one step and an enantiomeric excess of 98%. This intermediate bicyclic enal is fully primed with the appropriate functionality for attachment of the remaining groups. Access to this bicyclic enal will not only render existing prostaglandin-based drugs more affordable, but will also facilitate the rapid exploration of related chemical structures around the ubiquitous five-membered ring motif, such as potentially therapeutic prostaglandin analogues.

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