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首页> 外文期刊>Bioorganic and medicinal chemistry >Synthesis, photophysical properties of triazolyl-donor/acceptor chromophores decorated unnatural amino acids: Incorporation of a pair into Leu-enkephalin peptide and application of triazolylperylene amino acid in sensing BSA
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Synthesis, photophysical properties of triazolyl-donor/acceptor chromophores decorated unnatural amino acids: Incorporation of a pair into Leu-enkephalin peptide and application of triazolylperylene amino acid in sensing BSA

机译：三唑基供体/受体生色团修饰的非天然氨基酸的合成，光物理性质：将一对引入亮氨酸脑啡肽中并将三唑基戊二烯氨基酸用于传感BSA

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The research in the field of design and synthesis of unnatural amino acids is growing at a fast space for the increasing demand of proteins of potential therapeutics and many other diversified novel functional applications. Thus, we report herein the design and synthesis of microenvironment sensitive fluorescent triazolyl unnatural amino acids (UNAA) decorated with donor and/or acceptor aromatic chromophores via click chemistry. The synthesized fluorescent amino acids show interesting solvatochromic characteristic and/or intramolecular charge transfer (ICT) feature as is revealed from the UV-visible, fluorescence photophysical properties and DFT/TDDFT calculation. HOMO-LUMO distribution shows that the emissive states of some of the amino acids are characterized with more significant electron redistribution between the triazolyl moiety and the aromatic chromophores linked to it leading to modulated emission property. A pair of donor-acceptor amino acid shows interesting photophysical interaction property indicating a FRET quenching event. Furthermore, one of the amino acid, triazolyl-perylene amino acid, has been exploited for studying interaction with BSA and found that it is able to sense BSA with an enhancement of fluorescence intensity. Finally, we incorporated a pair of donor/acceptor amino acids into a Leu-enkephalin analogue pentapeptide which was found to adopt predominantly type II beta-turn conformation. We envisage that our investigation is of importance for the development of new fluorescent donor-acceptor unnatural amino acids a pair of which can be exploited for generating fluorescent peptidomimetic probe of interesting photophysical property for applications in studying peptide-protein interaction. (C) 2016 Elsevier Ltd. All rights reserved.
机译：在非天然氨基酸的设计和合成领域中的研究正在迅速发展，以增加对潜在治疗剂和许多其他多样化新颖功能应用的蛋白质需求。因此，我们在本文中报道了通过点击化学用供体和/或受体芳族发色团修饰的微环境敏感性荧光三唑基非天然氨基酸（UNAA）的设计和合成。合成的荧光氨基酸显示出有趣的溶剂变色特性和/或分子内电荷转移（ICT）特性，如从UV-可见光，荧光光物理特性和DFT / TDDFT计算中所揭示的那样。 HOMO-LUMO分布表明，某些氨基酸的发射态具有三唑基部分和与其相连的芳族发色团之间更显着的电子再分布特征，从而导致发射特性得到调节。一对供体-受体氨基酸显示出有趣的光物理相互作用特性，表明发生了FRET猝灭事件。此外，一种氨基酸三唑基-per氨基酸已被用于研究与BSA的相互作用，并发现它能够以增强的荧光强度来感测BSA。最后，我们将一对供体/受体氨基酸掺入了亮氨酸-脑啡肽类似物五肽中，发现该肽主要采用II型β-转弯构象。我们设想我们的研究对于开发新的荧光供体-受体非天然氨基酸很重要，该对氨基酸可用于产生有趣的光物理性质的荧光拟肽探针，用于研究肽-蛋白质相互作用。 （C）2016 Elsevier Ltd.保留所有权利。

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