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Quantitative 1 H NMR spectroscopy (qNMR) in the early process development of a new quorum sensing inhibitor
Magnetic Resonance in Chemistry ( IF 2 ) Pub Date : 2019-07-22 , DOI: 10.1002/mrc.4906
Robson A F Cavalcante 1 , Felipe L Silva 2 , Fernanda Favero 1, 2 , Inês S Resck 1 , Alex L Pereira 2 , Angelo H L Machado 1
Affiliation  

2‐methyl‐5,6,7,8‐tetrahydro‐2H‐chromen‐4(3H)‐one (called 6‐oxo) is presented as a new AI‐1 quorum sensing inhibitor for Vibrio harveyi. The development of a chemical process to afford traceable materials for new biological assays demands the development of analytical methods to ensure their purity and quality. This work describes the use of quantitative 1H nuclear magnetic resonance (NMR) spectroscopy (qNMR) to assess the purity of a sample of 6‐oxo (99.88%) and a sample of its major process impurity (E)‐1‐(2‐hydroxycyclohex‐2‐en‐1‐yl)but‐2‐en‐1‐one (called HCB; 98.28%). To explore the scope of the use of qNMR to quantify the amount of low‐content components in samples related to the chemical process for 6‐oxo synthesis, this work also determined the amount of 6‐oxo in two HCB samples: (a) the high‐purity HCB sample described above and (b) a crude HCB sample collected during the chemical process. Despite the complexity of the crude sample, the amount of 6‐oxo was readily assessed and could help to estimate the extent to which 6‐oxo was already formed during the HCB synthesis. This information can help the understanding of how the process parameters can be modified to improve the performance of the whole process, by controlling the reaction mechanisms working at each step of this chemical process. In this context, our results reinforce qNMR as a complementary analytical tool for the quantification of the main component found in a sample, contributing to the standardization of reference materials and thus allowing the development of analytical methods for process control and traceability of the samples used for biological assays.

中文翻译:

新型群体感应抑制剂早期工艺开发中的定量 1 H NMR 光谱 (qNMR)

2-methyl-5,6,7,8-tetrahydro-2H-chromen-4(3H)-one(称为 6-oxo)是哈维弧菌的一种新型 AI-1 群体感应抑制剂。为新生物测定提供可追溯材料的化学过程的开发需要开发分析方法以确保其纯度和质量。这项工作描述了使用定量 1 H 核磁共振 (NMR) 光谱 (qNMR) 来评估 6-oxo (99.88%) 样品及其主要工艺杂质 (E)-1-(2-羟基环己-2-烯-1-基)but-2-en-1-one(称为 HCB;98.28%)。为了探索使用 qNMR 来量化与 6-oxo 合成的化学过程相关的样品中低含量组分的量的范围,这项工作还确定了两个 HCB 样品中 6-oxo 的量:(a) 上述高纯度 HCB 样品和 (b) 在化学过程中收集的粗 HCB 样品。尽管粗样品很复杂,但 6-oxo 的量很容易评估,并且可以帮助估计在 HCB 合成过程中 6-oxo 已经形成的程度。通过控制在该化学过程的每个步骤中起作用的反应机制,这些信息可以帮助了解如何修改过程参数以提高整个过程的性能。在这种情况下,我们的结果加强了 qNMR 作为量化样品中主要成分的补充分析工具,有助于参考材料的标准化,从而允许开发用于过程控制和可追溯性的分析方法用于样品中生物测定。
更新日期:2019-07-22
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