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对映异构

乳酸手征性S-(+)-乳酸(左边)与R-(-)-乳酸(右边)彼此是对方不可叠加的镜像,是生物学中重要的对映体。更详细地说,S-(+)-乳酸的镜像是R-(-)-乳酸,不是S-(+)-乳酸,S-(-)-乳酸的镜像是R-(+)-乳酸,不是S-(-)-乳酸。

对映异构体(英语:Enantiomer (/ɪˈnæntiəmər, ɛ-, -ti-/[1] ə-NAN-tee-ə-mər)),又称对掌异构体光学异构体镜像异构体旋光异构体,不能与彼此立体镜像异构体完全重叠。[2][3]

互为镜像(mirror images)的分子。不对称碳原子和四种不同的原子或原子基团连结,不对称碳为手性中心。当有n个手性中心时,则最多有2的n次方立体异构体。

来源于希腊文,具有左手对右手那样镜像关系的一对物质。无论怎样摆布都不能使这些镜像成为同一物。有对称平面的物质不能是对映体,因为它和它的镜像是等同的。乳酸那样的分子对映体,除了与其他不对称分子的化学反应以及与偏振光作用外,具有完全相同的化学物质。对映体在结晶学中很重要,因为许多晶体是由单个分子的右手型和左手型交替排列的。对晶体的完整描述,就是要说明这些型体彼此间是如何混合的。两种光学活性的酒石酸,即所谓d-酒石酸和l-酒石酸就是一对对映体的实例。

历史

1849年,法国化学家路易·巴斯德Louis Pasteur)发现从在酿酒的容器中,取得的酒石酸盐可以使平面偏振光旋转,但是使用其他来源的酒石酸盐却无法测定出此性质。而此二者不同之处即是能否让平面偏极光旋转,原因就是此二者为光学异构体。

1874年,荷兰化学家范托夫Jacobus Henricus van 't Hoff)和法国化学家列贝尔英语Joseph Le Bel成功用连接到碳原子的四面体结构的理论解释此异构体种类的旋光性质。

注释

  1. ^ enantiomer - definition of enantiomer in English from the Oxford dictionary. OxfordDictionaries.com. [2016-01-20]. (原始内容存档于2016-05-12). 
  2. ^ Definition of antipodes - Chemistry Dictionary. www.chemicool.com. [2017-11-18]. (原始内容存档于2021-01-09) (美国英语). 
  3. ^ The Stereochemistry of Organic Compounds, Eliel, E. L.; Wilen, S. H., Wiley Interscience, New York, 1994, 1203. ISBN 0-471-01670-5, QD481.E52115 1993

参考文献

  • E. J. Ariëns, Stereochemistry, a basis for sophisticated nonsense in pharmacokinetics and clinical pharmacology, European Journal of Clinical Pharmacology. 1984, 26 (6): pp. 663–668, (德文) 
  • Uwe Meierhenrich, Amino acids and the asymmetry of life, Springer-Verlag. 2008, (德文) 

参阅

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对映异构
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