Porphyrins and metalloporphyrins: Versatile circular dichroic reporter groups for structural studies
Porphyrins and metalloporphyrins: Versatile circular dichroic reporter groups for structural studies
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DOI：
10.1002/(sici)1520-636x(2000)12:4
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发表时间：
2000-01-01
期刊：
影响因子：
2
通讯作者：
Berova, N
中科院分区：
文献类型：
--
作者：
Huang, XF;Nakanishi, K;Berova, N
在过去的几年中，卟啉和金属卟啉作为圆二色性（CD）研究的发色团引起了广泛的关注，圆二色性是监测手性相互作用不可或缺的手性光学工具。本综述总结了卟啉和金属卟啉、强大的 CD 生色团的多方面特性，其特征在于其强烈且红移的 Soret 带、进行 pi-pi 堆积的倾向、金属的轻松掺入以及易于变化的溶解度。这些特性使卟啉成为 CD 研究中最有吸引力和最敏感的发色团之一。它们为研究手性卟啉组装体、大有机分子、生物聚合物和微量化合物的立体化学提供了可能性。卟啉进行 pi-pi 堆积以及锌卟啉与胺配位的趋势使得 CD 激子手性方法能够扩展到仅包含一个立构中心的柔性化合物的构型分配。各种人工卟啉受体已被合成用于识别生物学上重要的手性客体，例如碳水化合物、氨基酸及其衍生物。宿主卟啉Soret带的诱导CD以高灵敏度反映了客体的身份和主/客体络合的结合模式。 (C) 2000 Wiley-Liss, Inc.
During the last few years, porphyrins and metalloporphyrins have attracted widespread attention as chromophores for studies in circular dichroism (CD), an indispensable chiroptical tool for monitoring chiral interactions. This review summarizes the multifaceted properties of porphyrins and metalloporphyrins, powerful CD chromophores that are characterized by their intense and red-shifted Soret band, propensity to undergo pi-pi stacking, facile incorporation of metals, and ease in varying solubility. Such attributes make porphyrins one of the most attractive and sensitive chromophores used in CD studies. They offer possibilities for studying the stereochemistry of chiral porphyrin assemblies, large organic molecules, biopolymers, and compounds available in miniscule quantities. The tendency of porphyrins to undergo pi-pi stacking and zinc porphyrins to coordinate with amines enable the CD exciton chirality method to be extended to configurational assignments of flexible compounds containing only one stereogenic center. Various artificial porphyrin receptors have been synthesized for the recognition of biologically important chiral guests such as carbohydrates, amino acids, and their derivatives. The induced CD of the host porphyrin Soret band reflects the identity of guests and binding modes of host/guest complexation with high sensitivity. (C) 2000 Wiley-Liss, Inc.