Structural determination of complex natural products by quantum mechanical calculations of 13C NMR chemical shifts: development of a parameterized protocol for terpenes
Structural determination of complex natural products by quantum mechanical calculations of 13C NMR chemical shifts: development of a parameterized protocol for terpenes
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DOI：
10.1007/s00894-016-3045-6
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发表时间：
2016-08-01
影响因子：
2.2
通讯作者：
de Amorim, Mauro Barbosa
中科院分区：
文献类型：
--
作者：
Ferreira de Albuquerque, Ana Carolina;Ribeiro, Daniel Joras;de Amorim, Mauro Barbosa
核磁共振（NMR）光谱是确定有机分子结构的最重要工具之一。尽管这项技术取得了进展，但对天然产物错误建立的结构的修订仍然普遍发表在文献中。在这种情况下，通过从头算和密度泛函理论（DFT）计算的化学位移的预测已成为一个非常强大的工具，以协助复杂的有机分子的结构测定。在这项工作中，我们提出了一个协议的发展C-13化学位移计算萜烯，一类天然产物，广泛分布于植物物种，是非常重要的，由于其生物和药理活性。该协议包括GIAO-DFT计算化学位移和应用参数化的比例因子，以确保这类天然产物的准确结构测定。该协议的应用，一组五个萜烯产生准确的计算化学位移，表明这是一个非常有吸引力的工具，如萜烯复杂的有机结构的计算。
Nuclear magnetic resonance (NMR) spectroscopy is one of the most important tools for determining the structures of organic molecules. Despite the advances made in this technique, revisions of erroneously established structures for natural products are still commonly published in the literature. In this context, the prediction of chemical shifts through ab initio and density functional theory (DFT) calculations has become a very powerful tool for assisting with the structural determination of complex organic molecules. In this work, we present the development of a protocol for C-13 chemical shift calculations of terpenes, a class of natural products that are widely distributed among plant species and are very important due to their biological and pharmacological activities. This protocol consists of GIAO-DFT calculations of chemical shifts and the application of a parameterized scaling factor in order to ensure accurate structural determination of this class of natural products. The application of this protocol to a set of five terpenes yielded accurate calculated chemical shifts, showing that this is a very attractive tool for the calculation of complex organic structures such as terpenes.