Chiral discrimination of alpha-hydroxy acids and N-Ts-alpha-amino acids induced by tetraaza macrocyclic chiral solvating agents by using H-1 NMR spectroscopy
文献类型：期刊论文
| 作者 | Lv, Caixia1; Feng, Lei1; Zhao, Hongmei2; Wang, Guo3; Stavropoulos, Pericles4; Ai, Lin1 |
| 刊名 | ORGANIC & BIOMOLECULAR CHEMISTRY
 |
| 出版日期 | 2017 |
| 卷号 | 15期号:7页码:1642-1650 |
| 英文摘要 | In the field of chiral recognition, reported chiral discrimination by H-1 NMR spectroscopy has mainly focused on various chiral analytes with a single chiral center, regarded as standard chiral substrates to evaluate the chiral discriminating abilities of a chiral auxiliary. Among them, chiral alpha-hydroxy acids, a-amino acids and their derivatives are chiral organic molecules involved in a wide variety of biological processes, and also play an important role in the area of preparation of pharmaceuticals, as they are part of the synthetic process in the production of chiral drug intermediates and protein-based drugs. In this paper, several alpha-hydroxy acids and N-Ts-alpha-amino acids were used to evaluate the chiral discriminating abilities of tetraaza macrocyclic chiral solvating agents (TAMCSAs) 1a-1d by 1H NMR spectroscopy. The results indicate that alpha-hydroxy acids and N-Ts-alpha-amino acids were successfully discriminated in the presence of TAMCSAs 1a-1d by H-1 NMR spectroscopy in most cases. The enantiomers of the alpha-hydroxy acids and N-Ts-alpha-amino acids were assigned based on the change of integration of the H-1 NMR signals of the corresponding protons. The enantiomeric excesses (ee) of N-Ts-alpha-amino acids 11 with different optical compositions were calculated based on the integration of the H-1 NMR signals of the CH3 protons (Ts group) of the enantiomers of (R)- and (S)-11 in the presence of TAMCSA 1b. At the same time, the possible chiral discriminating behaviors have been discussed by means of the Job plots of (+/-)-2 with TAMCSAs 1b and proposed theoretical models of the enantiomers of 2 and 6 with TAMCSA 1a, respectively. |
| 语种 | 英语 |
| 源URL | [http://ir.iccas.ac.cn/handle/121111/38153]  |
| 专题 | 化学研究所_其它 |
| 作者单位 | 1.Beijing Normal Univ, Coll Chem, Beijing 100875, Peoples R China 2.Chinese Acad Sci, Beijing Natl Lab Mol Sci, Inst Chem, Beijing 100190, Peoples R China 3.Capital Normal Univ, Dept Chem, Beijing 10048, Peoples R China 4.Missouri Univ Sci & Technol, Dept Chem, Rolla, MO 65409 USA |
| 推荐引用方式 GB/T 7714 | Lv, Caixia,Feng, Lei,Zhao, Hongmei,et al. Chiral discrimination of alpha-hydroxy acids and N-Ts-alpha-amino acids induced by tetraaza macrocyclic chiral solvating agents by using H-1 NMR spectroscopy[J]. ORGANIC & BIOMOLECULAR CHEMISTRY,2017,15(7):1642-1650. |
| APA | Lv, Caixia,Feng, Lei,Zhao, Hongmei,Wang, Guo,Stavropoulos, Pericles,&Ai, Lin.(2017).Chiral discrimination of alpha-hydroxy acids and N-Ts-alpha-amino acids induced by tetraaza macrocyclic chiral solvating agents by using H-1 NMR spectroscopy.ORGANIC & BIOMOLECULAR CHEMISTRY,15(7),1642-1650. |
| MLA | Lv, Caixia,et al."Chiral discrimination of alpha-hydroxy acids and N-Ts-alpha-amino acids induced by tetraaza macrocyclic chiral solvating agents by using H-1 NMR spectroscopy".ORGANIC & BIOMOLECULAR CHEMISTRY 15.7(2017):1642-1650. |
入库方式： OAI收割
来源：化学研究所
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