Chiralty Analysis on Chiral Molecular Recognition Using Mass Spectrometry

2014 Fiscal Year Final Research Report

• Project/Area Number: 24619015
• Research Category: Grant-in-Aid for Scientific Research (C)
• Allocation Type: Multi-year Fund
• Section: 一般
• Research Field: オミクス計測科学
• Research Institution: Osaka Municipal Technical Research Institute
• Principal Investigator: SHIZUMA Motohiro 地方独立行政法人大阪市立工業研究所, 生物・生活材料研究部, 研究主任 (40416318)
• Co-Investigator(Kenkyū-buntansha): KISO Taro 地方独立行政法人大阪市立工業研究所, 生物生活材料研究部, 研究主任 (90416313)
• Project Period (FY): 2012-04-01 – 2015-03-31
• Keywords: キラリティー / 質量分析 / エナンチオマー / ホスト-ゲスト化学 / 同位体標識 / キラルアミン / アミノ酸 / 光学純度

Outline of Final Research Achievements

The subject of this study is to establish new method for evaluation of chirality using mass spectrometry only. Chiral hosts were used to detect chirality in mass spectrometry. One enantiomer of the host was labeled with isotope atoms to distinguish each enantiomer in mass spectrometry. Pairs of isotope labeled enantiomer and the other unlabeled enantiomer of hosts such as chiral crown ethers were synthesized to recognize enantiomers of chiral ammonium ions. For free amino acids, labeled/unlabeled enantiomeric pair of copper complex was synthesized. The chiral crown ethers showed high chiral discrimination ability toward chiral ammonium ion guest in FABMS. That ability of the chiral hosts was clarified to depend on the steric structure neighboring the stereo-center of the guests. The correlation between the steric factors of the guests and the results of MS was found in multivariate analysis. Using copper complex, enantiomeric excess of free amino acids was determined using ESIMS.

Free Research Field

質量分析