手性化合物绝对构型确定的方法与应用

doi:10.6023/cjoc202108047

有机化学 ›› 2022, Vol. 42 ›› Issue (2): 424-433.DOI: 10.6023/cjoc202108047 上一篇下一篇

综述与进展

手性化合物绝对构型确定的方法与应用

葛锐^a, 朱园园^b, 王海峰^a^,^c^,^*(), 古双喜^a^,^c^,^*()

a 武汉工程大学化工与制药学院绿色化工过程教育部重点实验室武汉 430205
b 武汉工程大学化学与环境工程学院武汉 430205
c 武汉工程大学新型反应器与绿色化学工艺湖北省重点实验室武汉 430205

收稿日期:2021-08-24 修回日期:2021-09-18 发布日期:2022-02-24
通讯作者: 王海峰, 古双喜
基金资助:
国家自然科学基金(21877087); 国家自然科学基金(22074114); 国家自然科学基金(20602164); 湖北省自然科学基金(2020CFB623); 绿色化工过程教育部重点实验室开放基金(GCP20200201); 新型反应器与绿色化学工艺湖北省重点实验室(武汉工程大学)开放基金(40201002)

Methods and Application of Absolute Configuration Assignment for Chiral Compounds

Rui Ge^a, Yuanyuan Zhu^b, Haifeng Wang^a^,^c(), Shuangxi Gu^a^,^c()

a Key Laboratory for Green Chemical Process of Ministry of Education, School of Chemical Engineering & Pharmacy, Wuhan Institute of Technology, Wuhan 430205
b School of Chemistry and Environmental Engineering, Wuhan Institute of Technology, Wuhan 430205
c Hubei Key Laboratory of Novel Reactor and Green Chemical Technology, Wuhan Institute of Technology, Wuhan 430205

Received:2021-08-24 Revised:2021-09-18 Published:2022-02-24
Contact: Haifeng Wang, Shuangxi Gu
Supported by:
National Natural Science Foundation of China(21877087); National Natural Science Foundation of China(22074114); National Natural Science Foundation of China(20602164); Natural Science Foundation of Hubei Province(2020CFB623); Key Laboratory for Green Chemical Process of Ministry of Education Open Fund(GCP20200201); Hubei Key Laboratory of Novel Reactor and Green Chemical Technology (Wuhan Institute of Technology) Open Fund(40201002)

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摘要/Abstract

手性分子绝对构型(AC)的确定在手性化学研究与应用中至关重要. 近年测定手性化合物AC的各种方法, 根据其原理可主要分为三大类. 第一类是在手性环境下激发手性化合物的原子核从而测定手性化合物AC的核磁共振(NMR)法, 包括应用芳环抗磁屏蔽效应的NMR法和应用配糖位移效应的NMR法; 第二类是基于原子共振散射的X射线衍射(XRD)法, 包括单晶和粉末XRD; 第三类是基于对映异构体对偏振光的折射和吸收不同从而测定手性化合物AC的光谱法, 包括旋光光谱法、电子圆二色谱法、振动圆二色谱法和振动拉曼光谱法. 此外, 还有一些其它方法如酶法和3,4-二氢-2-苯基-2H-嘧啶并[2,1-b]苯并噻唑(HBTM)法. 作者结合在手性荧光识别和手性药物领域的研究经历, 对上述方法的原理和应用进行了综述, 以期为手性化学及相关工作者提供有益的参考.

关键词: 手性化学, 手性化合物, 绝对构型确定, 核磁共振(NMR)法, X射线衍射(XRD)法, 光谱法

The absolute configuration (AC) assignment of chiral molecules is crucial to the research and application of chiral chemistry. In recent years, various methods for the AC determination for chiral compound fall mainly into three categories according to their principles. The first is the nuclear magnetic resonance (NMR)-based method for determining the AC of chiral compound by exciting the nucleus of the chiral compound in the chiral environment, including the NMR-based method using aromatic ring diamagnetic shielding effect and the NMR method using sugar shift effect. The second is X-ray diffraction (XRD) methods based on atomic resonance scattering, including single crystal and powder XRD. The third is based on the enantiomer refraction and absorption of polarized light, including optical rotation spectroscopy, electronic circular dichroism, vibration circular dichroism and vibration Raman spectroscopy. In addition, other methods such as enzyme-based and homobenzotetramisole (HBTM)-based methods are supplementary. Based on our research experiences in chiral fluorescent recognition and chiral drugs, the principles and application of these methods, aiming to afford beneficial references for chiral chemists and related workers are reviewed.

Key words: chiral chemistry, chiral compounds, absolute configuration assignment, nuclear magnetic resonance (NMR), X-ray diffraction (XRD), spectroscopy

引用此文

葛锐, 朱园园, 王海峰, 古双喜. 手性化合物绝对构型确定的方法与应用[J]. 有机化学, 2022, 42(2): 424-433.

Rui Ge, Yuanyuan Zhu, Haifeng Wang, Shuangxi Gu. Methods and Application of Absolute Configuration Assignment for Chiral Compounds[J]. Chinese Journal of Organic Chemistry, 2022, 42(2): 424-433.

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图/表 12

图1. 绝对构型确定的方法总览

Figure 1. An overview of absolute configuration determination methods

图2. 改进的Mosher酯构型模式图

Figure 2. Diagram of modified Mosher ester configuration pattern

图3. 化合物1~3的双MPA酯的ΔδRS值

Figure 3. ΔδRS values for bis-MPA esters of compounds 1~3

图4. 不同芳基甲氧基乙酸的化学结构

Figure 4. Chemical structures of various aryl methoxy acetic acids

图5. MBNC和MNCB的化学结构

Figure 5. Chemical structures of MBNC and MNCB

图6. THENA, THENA-d2和F-THENA试剂的化学结构

Figure 6. Chemical structures of THENA, THENA-d2 and F-THENA reagents

图8. (a) β-岩藻呋喃糖与α-阿拉伯呋喃糖的两个对映体结构; (b)叔醇类化合物4~6的Δδ值

Figure 8. (a) Structure of two enantiomers of β-fucofuranoside and α-arabinofuranoside; (b) Δδ values of tertiary alcohols 4~6

图9. XRD原理示意图

Figure 9. Schematic diagram of XRD

图10. 化合物7的晶体结构

Figure 10. Crystal structure of compound 7

图11. ECD原理示意图

Figure 11. Schematic diagram of ECD

图12. 化合物8~10的化学结构

Figure 12. Chemical structures of compounds 8~10

图13. HBTM法确定仲醇绝对构型

Figure 13. Absolute configuration of secondary alcohols by the HBTM catalyst

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手性化合物绝对构型确定的方法与应用

Methods and Application of Absolute Configuration Assignment for Chiral Compounds

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