特定氨基酸对映体的化学选择性和对映选择性荧光鉴定,Chemical Communications

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特定氨基酸对映体的化学选择性和对映选择性荧光鉴定
Chemical Communications ( IF 4.3 ) Pub Date : 2022-06-07 , DOI: 10.1039/d2cc02363f
Lin Pu ₁

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手性氨基酸的对映异构体在包括人类在内的生物系统中发挥着多种作用。它们在各种手性有机化合物的不对称合成中也非常有用。因此，识别特定氨基酸并将其与其对映异构体区分开来非常重要。尽管在氨基酸荧光探针的开发方面取得了重大进展，但它们中的大多数不能同时进行特定氨基酸对映体的化学选择性和对映选择性检测。在本文中，设计和合成了几种荧光探针，用于对某些氨基酸对映异构体的化学选择性和对映选择性识别。( S )- 1在L存在下显示出显着增强的荧光-谷氨酸和L-天冬氨酸，但对它们的相反对映异构体和其他氨基酸不产生或产生很少的荧光反应。( R )- 4与Zn ²⁺组合在L-丝氨酸存在下显示出显着增强的荧光。( S )- 6设计用于选择性识别组氨酸。由两亲二嵌段共聚物制成的胶束用于包封水不溶性化合物 ( S ) -8 ，该化合物在 Zn ²⁺存在下显示出化学选择性和对映选择性荧光增强与L-赖氨酸在水溶液中。相同的胶束还用于封装几种 ( S )-1,1'-联萘基单醛 ( S ) -10 ，用于在 Zn ²⁺存在下对L-色氨酸进行化学选择性和对映选择性荧光识别在水溶液中。这些发现表明，通过在 1,1'-联萘的指定位置掺入某些官能团，可以实现对特定氨基酸对映异构体的高选择性荧光鉴定。这些探针的联萘核心结构提供了手性来源和高度可调的荧光特性。将这些探针的结构和手性与特定氨基酸对映体的结构和手性相匹配，可以产生结构刚性的反应产物，并产生显着增强的荧光。这项工作的策略可以进一步扩展，以开发用于特异性识别许多感兴趣的氨基酸的荧光探针。这应该有助于在各种应用中分析手性氨基酸。

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Chemoselective and enantioselective fluorescent identification of specific amino acid enantiomers

The enantiomers of chiral amino acids play versatile roles in biological systems including humans. They are also very useful in the asymmetric synthesis of diverse chiral organic compounds. Therefore, identifying a specific amino acid and distinguishing it from its enantiomer are of great importance. Although significant progress has been made in the development of fluorescent probes for amino acids, most of them are not capable of conducting simultaneous chemoselective and enantioselective detection of a specific amino acid enantiomer. In this article, several fluorescent probes have been designed and synthesized for chemoselective as well as enantioselective recognition of certain amino acid enantiomers. (S)-1 shows greatly enhanced fluorescence in the presence of L-glutamic acid and L-aspartic acid, but produces no or little fluorescence response toward their opposite enantiomers and other amino acids. (R)-4 in combination with Zn²⁺ shows greatly enhanced fluorescence in the presence of L-serine. (S)-6 is designed for the selective recognition of histidine. Micelles made of an amphiphilic diblock copolymer are used to encapsulate the water-insoluble compound (S)-8 which shows chemoselective as well as enantioselective fluorescence enhancement with L-lysine in the presence of Zn²⁺ in aqueous solution. The same micelles are also used to encapsulate several (S)-1,1′-binaphthyl-based monoaldehydes (S)-10 for the chemoselective and enantioselective fluorescence recognition of L-tryptophan in the presence of Zn²⁺ in aqueous solution. These findings have demonstrated that highly selective fluorescence identification of a specific amino acid enantiomer can be achieved by incorporating certain functional groups at the designated locations of the 1,1′-binaphthyls. The binaphthyl core structure of these probes provides both a chirality source and highly tunable fluorescence properties. Matching the structure and chirality of these probes with those of the specific amino acid enantiomers can generate structurally rigid reaction products and give rise to greatly enhanced fluorescence. The strategies of this work can be further expanded to develop fluorescent probes for the specific identification of many amino acids of interest. This should facilitate the analysis of chiral amino acids in various applications. The outlook of this research and its comparison with other methods are also discussed.

更新日期：2022-06-07

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