Computational Prediction of Diastereomeric Separation Behavior of Fluorescent <i>o</i>-Phthalaldehyde Derivatives of Amino Acids

• TODOROKI Kenichiro

  Laboratory of Analytical and Bio-Analytical Chemistry, School of Pharmaceutical Sciences, University of Shizuoka

• NAKANO Tatsuki

  Laboratory of Analytical and Bio-Analytical Chemistry, School of Pharmaceutical Sciences, University of Shizuoka

• WATANABE Hiroki

  Laboratory of Analytical and Bio-Analytical Chemistry, School of Pharmaceutical Sciences, University of Shizuoka

• MIN Jun Zhe

  Laboratory of Analytical and Bio-Analytical Chemistry, School of Pharmaceutical Sciences, University of Shizuoka

• INOUE Koichi

  Laboratory of Analytical and Bio-Analytical Chemistry, School of Pharmaceutical Sciences, University of Shizuoka

• ISHIKAWA Yoshinobu

  Laboratory of Physical Chemistry, School of Pharmaceutical Sciences, University of Shizuoka

• TOYO’OKA Toshimasa

  Laboratory of Analytical and Bio-Analytical Chemistry, School of Pharmaceutical Sciences, University of Shizuoka

Bibliographic Information

Other Title

• Computational Prediction of Diastereomeric Separation Behavior of Fluorescent o-Phthalaldehyde Derivatives of Amino Acids

Abstract

We have developed a convenient method for predicting the LC resolution of amino acid diastereomers through computational calculations. For acquiring experimental data, we derivatized 10 amino acids using o-phthalaldehyde and N-acetyl-L-cysteine as fluorogenic diastereomer-forming reagents and analyzed the diastereomers using reversed-phase LC and fluorescence detection. For theoretical chemical calculations, we used the publicly available semi-empirical calculation software MOPAC2012. Using the obtained experimental and theoretical data, we determined the change in analytical resolution with differences in the structure of the diastereomers. From the results obtained, we concluded that greater conformational change through diastereomeric derivatization induced an increase in the contact area with the stationary phase, leading to higher resolution.

Journal

• Analytical Sciences

  Analytical Sciences 30 (9), 865-870, 2014

  The Japan Society for Analytical Chemistry

Keywords

• Amino acid
• chiral derivatization
• computational calculation
• diastereomer
• liquid chromatography

Details

• CRID: 1390001204260574464
• NII Article ID: 130004687412
• NII Book ID: AA10500785
• DOI: 10.2116/analsci.30.865
• COI: 1:STN:280:DC%2BC2M7gslKjug%3D%3D
• ISSN: 13482246
• ISSN: 09106340
• NDL BIB ID: 025775300
• PubMed: 25213814
• Web Site: https://ndlsearch.ndl.go.jp/books/R000000004-I025775300
• Web Site: https://link.springer.com/content/pdf/10.2116/analsci.30.865.pdf
• Web Site: https://link.springer.com/article/10.2116/analsci.30.865/fulltext.html
• Web Site: https://www.jstage.jst.go.jp/article/analsci/30/9/30_865/_pdf
• Web Site: https://search.jamas.or.jp/link/ui/2015159927
• Text Lang: en
• Data Source:
  • JaLC
  • NDL
  • Crossref
  • PubMed
  • CiNii Articles
  • KAKEN
• Abstract License Flag: Disallowed