Enantioselektive Unterscheidung von Cannabis-verwandten flüchtigen organischen Verbindungsgemischen durch Sensorarrays basierend auf nanoporösen chiralen metallorganischen Gerüstfilmen

尽管在大多数生物过程中至关重要，但手性分子及其分子混合物的技术识别是一项特别具有挑战性的重要任务。基于我们在第一个资助期的成果，我们将实现一个通用的立体选择性传感器，包括对挥发性有机化合物的区域选择性、非对映选择性和对映体选择性检测。本项目旨在建立一种简单、廉价的手性电子鼻，用于精确传感各种手性分子混合物。该系统由多达16个独立的石英晶体微天平(QCM)传感器组成，这些传感器涂覆了不同的同手性纳米多孔金属-有机骨架(MOF)膜，这些膜是由基于[2.2]对环芳烃和BINOL的定制同手性连接物制成的。不同的、明确定义的晶体同手性MOF结构导致了功能性手性孔和手性客体分子之间的特定(对映选择性)相互作用。因此，每个QCM传感器的响应将是不同的，从而产生每个分子的指纹。复杂的数据将使用先进的机器学习算法进行评估。因此，电子鼻系统将允许准确识别手性分子。在试点试验中，我们将专注于手性气味分子的准确识别，传统传感器无法区分这些分子，尽管它们的气味截然不同。稍后，我们将针对药物和天然大麻素，精确区分和量化与挥发性有机大麻成分(THC和其他代谢物)相关的生物活性药物和萜类的关键对映体。这一点很重要，因为这是工业化生产的，因此可以区分常规大麻制剂，这是一个有趣和重要的质量特征。与大麻有关的不同化合物的组成可以被视为一种“个人指纹”，它因大麻品种/品系的不同而不同，甚至可能因种植或储存条件的不同而不同。因此，分析大麻以进行准确鉴定的具体和简单的选择是法医学、过程中的质量控制和禁毒执法机构(在德国，警方)的重要工具。

Although crucial in most biological processes, the technical discrimination of chiral molecules and their molecular mixtures is an exceptionally challenging but important task. Based on our results during the first funding period, we will realize a general stereoselective sensor comprising regioselective, diastereoselective, and enantioselective detection of volatile organic compounds. This project aims to set up a simple and low-priced chiral electronic nose (e-nose) for precisely sensing various chiral molecular mixtures. The system is composed of up to 16 individual Quartz Crystal Microbalances (QCM) sensors, which are coated with different homochiral nanoporous metal-organic framework (MOF) films made of custom-made homochiral linkers based on [2.2] paracyclophane and BINOL. The different, well-defined crystalline homochiral MOF structures result in specific (enantioselective) interactions between the functional chiral pores and the chiral guest molecules. Thus, the response of each QCM sensor will be different, resulting in a fingerprint of each molecule. The complex data will be evaluated with advanced machine-learning algorithms. As a result, the e-nose system will allow the accurate discrimination of chiral molecules. In a pilot trial, we will focus on the accurate discrimination of chiral odor molecules, which conventional sensors cannot discriminate, although their odors are vastly different. Later, we will target drugs and natural cannabinoids to precisely discriminate and quantify the crucial enantiomers of bioactive drugs and terpenes related to volatile organic cannabis ingredients (THC and other metabolites). This is important since industrially produced, and conventional cannabis preparations can thus be distinguished, which is an interesting and important quality feature. The composition of the different compounds related to cannabis can be seen as a kind of "individual fingerprint”, which differs from one cannabis cultivar/strain to another but could even differ in one strain depending on the cultivation or storage conditions. Therefore, specific and easy options to analyze cannabis for exact identification are vital tools for forensic medicine, quality controls within the process, and drug-enforcement agencies (in Germany, the police).