FENG Leining,ZHANG Bo,JIN Youxi,et al.Synthesis of chiral derivatization reagent PPZ - Pro - NHS and its application in D/L - amino acids separation[J].Journal of Yanbian University,2021,47(03):260-265.
手性衍生化试剂PPZ - Pro - NHS的合成及其在D/L- 氨基酸分离中的应用
- Title:
- Synthesis of chiral derivatization reagent PPZ - Pro - NHS and its application in D/L - amino acids separation
- 文章编号:
- 1004-4353(2021)03-0260-06
- 关键词:
- 手性; 氨基酸; 衍生化试剂; PPZ - Pro - NHS
- Keywords:
- chirality; amino acids; derivatization reagent; PPZ - Pro - NHS
- 分类号:
- O658.9
- 文献标志码:
- A
- 摘要:
- 以(S)-1-(5-(4- 甲基哌嗪-1- 基)-2,4- 二硝基苯基)吡咯烷 -2- 羧酸(PPZ - Pro)和N- 羟基琥珀酰亚胺(NHS)为反应物合成了一种新型衍生化试剂(S)-2,5- 二氧吡咯烷 -1- 基 -1-(5-(4- 甲基哌嗪 -1- 基)-2,4- 二硝基苯基)吡咯烷 -2- 羧酸酯(PPZ - Pro - NHS),并采用核磁共振波谱法(1H NMR、13C NMR)和质谱(MS)对其结构进行了表征.研究显示:在碱性介质中 PPZ - Pro - NHS与氨基酸反应生成非对映体氨基酸衍生物,且当在反应条件为100 mmol/L三乙胺介质、反应温度为25 ℃和反应时间为40 min条件下所生成的非对映体氨基酸衍生物的色谱峰面积最大.以水- 乙腈为流动相,用C18柱对19种氨基酸对映体进行分离显示,其分离度(Rs)大于1.20(除天冬氨酸外),达到基线分离.因此,制备的PPZ - Pro - NHS在氨基酸对映体和手性药物的分离和分析方面具有较好的应用前景.
- Abstract:
- A new derivatization reagent(S)- 2,5 - dioxypyrrolidine - 1 - yl - 1 -(5 -(4 - methylpiperazine - 1 - yl)- 2,4 -dinitrophenyl)pyrrolidine - 2 - carboxylic acid ester(PPZ - Pro - NHS)was synthesized from(S)- 1 -(5 -(4 - methylpiperazine - 1 - yl)- 2,4 - dinitrophenyl)pyrrolidine - 2 - carboxylic acid(PPZ - Pro)and N - hydroxysuccinimide(NHS).Its structure was characterized bynuclearmagnetic resonance spectroscopy(1H NMR, 13C NMR)and mass spectroscopy(MS).The reswults showed that in alkaline medium, PPZ - Pro - NHS reacts with amino acidsto produce the diastereomeric derivatives of amino acids, and the highest peak area of amino acid derivatives was obtained when the reaction conditions were 100 mmol/L triethylamine medium, reaction temperature 25 ℃ and reaction time 40 min. Nineteen kinds of amino acid enantiomers were separated by C18 column with water - acetonitrile as mobile phase. The resolution(Rs)was greater than 1.20(except aspartic acid), which reached the baseline separation. Therefore, PPZ - Pro - NHS will have a good application prospect in the separation and analysis of amino acid enantiomers and chiral drugs.
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备注/Memo
收稿日期: 2021-06-23
基金项目: 国家自然科学基金(22064017)
*通信作者: 金东日(1965—),男,博士,教授,研究方向为药物分析.