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Article Abstract

A robust and efficient enantioselective separation of racemic menthol was achieved on a standard C column with reverse-phase high-performance liquid chromatography (RP-HPLC) and UV detector. (R)-α-hydroxy-4-methylbenzeneacetic acid was utilized as the pre-column derivatization reagent. The impact of mobile phase composition on diastereomer selectivity was thoroughly investigated, resulting in a high resolution of 2.11 under optimized conditions. The method was rigorously validated for linearity, precision, accuracy, limit of detection (LOD) and limit of quantification (LOQ). Notably, a separation pre-screening mechanism (SPM) and a prediction model was developed based on density functional theory (DFT) studies. This model elucidated the relationship between molecular polarity differences (△MPI) and chromatographic behavior, facilitating the interpretation and prediction of racemic menthol resolution with various chiral derivatization reagents. The present work not only presents an efficient and economical approach for menthol enantiomeric separation, but also offers valuable insights for the innovative design and advancement of chromatographic methodologies for a wide array of chiral enantiomers.

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http://dx.doi.org/10.1016/j.talanta.2024.127062DOI Listing

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Article Synopsis
  • A highly effective enantioselective separation of racemic menthol was achieved using reverse-phase high-performance liquid chromatography (RP-HPLC) and a specific derivatization reagent, resulting in improved resolution.
  • The study explored how mobile phase composition affects the separation of diastereomers, leading to a high resolution value of 2.11 under optimized conditions.
  • A separation pre-screening mechanism and a prediction model based on computational studies were developed, enhancing understanding of how molecular properties influence chromatographic behavior and aiding future developments in separating chiral compounds.
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N-terminal truncation (N-) and directional proton transfer in an old yellow enzyme enables tunable efficient producing (R)- or (S)-citronellal.

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