对映体选择性高效液相色谱法与光谱方法和理论计算相结合：确定丁香酚衍生物绝对构型的有效策略。

IF 2.8 4区化学 Q2 CHEMISTRY, ANALYTICAL

Chirality Pub Date : 2024-05-15 DOI:10.1002/chir.23668

Simone Manetto, Giulia Mazzoccanti, Gaia Pulitelli, Sofia Niccolai, Damiano Tanini, Marco Pierini, Roberto Cirilli

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引用次数: 0

摘要

通过基于对映体选择性高效液相色谱法的多步骤方法，结合光谱和理论计算，确定了三种手性丁香酚衍生物的绝对构型。在固定淀粉手性固定相 Chiralpak IG 上，采用正相洗脱条件，通过 HPLC 分离出用于立体化学表征的毫克级对映体。通过甲氧基-α-三氟甲基-α-苯乙酸衍生化（莫舍尔酸），用 1H NMR 间接测定了三种化合物之一的绝对构型。实验和预测电子圆二色光谱的比较证实了莫舍尔法的立体化学分配，并将绝对构型分配扩展到另外两种手性化合物。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

Enantioselective high-performance liquid chromatography combined with spectroscopic methods and theoretical calculations: A valid strategy to determine the absolute configuration of eugenol derivatives

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The absolute configuration of three chiral eugenol derivatives was assigned by a multi-step methodology based on enantioselective HPLC combined with spectroscopic and theoretical calculations. Milligram amounts of enantiopure forms used for stereochemical characterization were isolated by HPLC on the immobilized amylose-based chiral stationary phase Chiralpak IG using normal phase elution conditions. The absolute configuration was indirectly determined for one of the three compounds by ¹H NMR via methoxy-α-trifluoromethyl-α-phenylacetic acid derivatization (Mosher's acid). Comparison of the experimental and predicted electronic circular dichroism spectra confirmed the stereochemical assignment by Mosher's method and extended the absolute configuration assignment to two other chiral compounds.

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来源期刊

Chirality 医学-分析化学

CiteScore

4.40

自引率

5.00%

发文量

124

审稿时长

1 months

期刊介绍： The main aim of the journal is to publish original contributions of scientific work on the role of chirality in chemistry and biochemistry in respect to biological, chemical, materials, pharmacological, spectroscopic and physical properties. Papers on the chemistry (physiochemical, preparative synthetic, and analytical), physics, pharmacology, clinical pharmacology, toxicology, and other biological aspects of chiral molecules will be published.