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化学进展 2021, Vol. 33 Issue (12): 2316-2333 DOI: 10.7536/PC201123 前一篇   后一篇

• 综述 •

质谱光电离/解离技术和生物分子结构鉴定

杨笑宇, 贾珊珊, 张娟, 亓英华, 胡雪雯, 沈宝洁, 钟鸿英*()   

  1. 华中师范大学化学学院质谱实验室 农药和化学生物学教育部重点实验室 武汉 430079
  • 收稿日期:2020-11-18 修回日期:2021-04-05 出版日期:2021-12-20 发布日期:2021-12-27
  • 通讯作者: 钟鸿英
  • 基金资助:
    国家自然科学基金项目(21834002)
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Photo Ionization and Dissociation in Mass Spectrometry for Structural Identification of Biological Molecules

Xiaoyu Yang, Shanshan Jia, Juan Zhang, Yinghua Qi, Xuewen Hu, Baojie Shen, Hongying Zhong()   

  1. Laboratory of Mass Spectrometry, College of Chemistry, Central China Normal University, Key Laboratory of Pesticides and Chemical Biology of Ministry of Education,Wuhan 430079, China
  • Received:2020-11-18 Revised:2021-04-05 Online:2021-12-20 Published:2021-12-27
  • Contact: Hongying Zhong
  • Supported by:
    the National Natural Science Foundation of China(21834002)

质谱是一种广泛应用于化学、生物医学、药学、环境、农业和能源等各领域的分子结构鉴定技术,这种技术通过准确测定分子离子和碎片离子的质量-电荷比来推导分子结构。如何将试样中待测组分有效气化、离子化,转变为具有不同质-荷比的气态离子是质谱仪器和分析方法研究的关键。基于不同物理化学原理的电离、解离方法各有特点,适合不同分析目的。常见的软电离技术一般产生稳定的偶电子离子,往往需要与其他技术联用才能实现分子离子的进一步解离。除了基于碰撞活化和电子得失的两类常见解离方法,光解离技术利用波长/能量可调控的光辐射来使样品分子电离,并引发特定化学键断裂。本文旨在综述不同电离/解离技术,重点探讨近年来发展的红外和紫外光电离/解离技术基本工作原理、仪器特点及其在生物分子(包括有机小分子、蛋白质、核酸和多糖等)结构鉴定中的应用。

关键词： 红外, 紫外, 光电离/解离, 质谱分析, 生物分子

Mass spectrometry is an analytical technique that has been extensively used in the areas of chemistry, biomedicine, pharmacology, environment, agriculture and energy. It is based on the detection of accurate mass-to-charge ratios of molecular ions and fragment ions for the structural identification of diverse biological molecules. How to efficiently ionize and dissociate neutral molecules present in various samples and generate positive or negative ions are the key to the instrumentation of mass spectrometry and the development of enabling analytical methods. There are various ionization and dissociation techniques based on different physical chemical mechanisms that have unique advantages suitable for specific analytical goals. Most soft ionization techniques generate ions with even-numbered electrons that are very stable and need the coupling to other dissociation techniques for further molecular fragmentation. Besides those techniques based on collision activation and electron gains/losses, photo irradiation based techniques can provide wavelength/energy adjustable photons to initiate specific cleavages of chemical bonds. This work is aimed to review fundamental principles and instrumentations of infrared and ultraviolet photo-induced ionization and dissociation. The application to the analysis of different biological molecules including small organic molecules, proteins, nucleic acids, lipids and carbohydrates are also addressed.

Contents

1 Introduction

2 Overview of ionization techniques in mass spectrometry

2.1 Electron impact/electron capture ionization

2.2 Electrospray ionization and matrix assisted ionization

2.3 Surface ionization

2.4 Atomic/ionic beam ionization

3 Overview of dissociation techniques in mass spectrometry

4 Fundamental principles of photo ionization/dissociation

4.1 Direct photo ionization and dissociation

4.2 Coupling of photo dissociation with other ionization techniques

5 Instrumentation

5.1 Infrared multiphoton dissociation

5.2 Ultraviolet photo dissociation

6 Structural identification of biomolecules

6.1 Small organic molecules

6.2 Monosaccharides and polysaccharides

6.3 Peptides/proteins

6.4 Nucleic acids

7 Conclusion and prospect

Key words: infrared, ultraviolet, photoionization and dissociation, mass spectrometric analysis, biological molecules
()
图1 多肽的不同解离方式。(A)不同化学键断裂及其特征碎片离子;(B)典型解离技术和仪器
Fig.1 Dissociation pathways of peptides. (A) Chemical bond cleavages and resulting characteristic fragment ions; (B) representative dissociation techniques and instruments
图2 激光解吸电离甲基紫的两种途径。(A)激光热效应直接气化固态甲基紫盐酸盐;(B)激光激励中性甲基紫丢失低电离电位电子
Fig.2 Laser desorption dissociation of methyl violet. (A) Direct evaporation of solid methyl violet hydrochloride by laser heating effect; (B) Losses of low ionization potential electrons of neutral methyl violet by laser excitation
表1 质谱中不同电离技术的原理及应用
Table 1 Principle and application of different ionization techniques in mass spectrometry
No. Ionization Principles and products Molecular ions Fragment ions Whether the coupling to other techniques for fragmentation is needed (Y/N) Applications
1 Electron-initiated ionization Electron impact
(EI)		 Loss of electrons with low ionization potential
Radical cation		 Ions with odd-numbered electrons Radical/charge-initiated homolytic or heterolytic bond cleavages N Volatile small organic molecules
Laser activated
electron tunneling
(LAET)		 Electron capture by charge deficient atoms
Radical anions		 Ions with odd-numbered electrons Radical/charge-initiated homolytic or heterolytic bond cleavages N small organic molecules
2 Electrospray ionization (ESI) Protonation/deprotonation
Metal ion adducts		 Ions with even-numbered electrons
multiple-charged ions		 Difficult to occur spontaneously Y
Collision-activated dissociation, electron transfer dissociation and photo dissociation		 biological macromolecules/small organic molecules
3
Matrix assisted laser desorption ionization (MALDI)		 Protonation/deprotonation

Metal ion adducts		 Ions with even-numbered electrons Difficult to occur spontaneously Y

Collision-activated dissociation and photo dissociation		 biological macromolecules
4 Surface ionization Surface Enhanced Laser Desorption Ionization
(SALDI)		 Protonation/deprotonation

Metal ion adducts		 Ions with even-numbered electrons Difficult to occur spontaneously Y
Collision-activated dissociation and photo dissociation		 biological macromolecules/small organic molecules
Desorption Ionization on Porous Silicon (DIOS) Protonation/deprotonation
Metal ion adducts		 Ions with even-numbered electrons Difficult to occur spontaneously Y
Collision-activated dissociation and photo dissociation		 biological macromolecules/small organic molecules
Nanostructure-Initiator Mass Spectrometry (NIMS) Protonation/deprotonation
Metal ion adducts		 Ions with even-numbered electrons Difficult to occur spontaneously Y
Collision-activated dissociation and photo dissociation		 biological macromolecules/small organic molecules
5 Atomic/ion beam ionization Fast Atom Bombardment (FAB) Protonation/deprotonation
Metal ion adducts		 Ions with even-numbered electrons Difficult to occur spontaneously Y
Collision-activated dissociation		 Polypeptide/small organic molecules
Secondary Ion Mass Spectrometry (SIMS) Positive/negative ions Ions with even-numbered electrons Vibration activated dissociation N Material elements/small organic molecules/insulators
Desorption Electrospray Ionization (DESI) Protonation/deprotonation
Metal ion adducts		 Ions with even-numbered electrons
multiple-charged ions		 Difficult to occur spontaneously Y
Collision-activated dissociation, electron transfer dissociation and photo dissociation		 biological macromolecules/small organic molecules
图3 红外多光子解离与电子轰击电离的比较。(A)电子轰击产生的自由基中心和正电荷中心及其引发的化学键断裂;(B)红外多光子振动激活的化学键断裂
Fig.3 Comparison of infrared multiphoton dissociation and electron impact ionization. (A) Radical/charge centers generated by electron impact ionization and resultant chemical bond cleavages; (B) Infrared multiphoton activated chemical bond cleavages
图4 三种芳香氨基酸的紫外光解离和特征中性丢失
Fig.4 Ultraviolet photo ionization and characteristic neutral losses of three aromatic amino acids
图5 药物和生物小分子的红外多光子解离机理。(A)头孢菌素,(B)青霉素,(C)叶绿素
Fig.5 Mechanisms of infrared multiphoton dissociation of drugs and biological small molecules. (A) Cephalosporins,(B) Penicillin, (C) Chlorophyl
图6 单糖和多糖的红外多光子解离。(A)红霉素,(B)新霉素
Fig.6 Infrared multiphoton dissociation of monosaccharides and polysaccharides. (A) Erythromycin, (B) Neomycin
图7 多糖的紫外光电离
Fig.7 Ultraviolet photo dissociation of oligosaccharides
图8 蛋白质/多肽的真空紫外光解离
Fig.8 Vacuum ultraviolet photo dissociation of peptides/proteins
图9 核酸的红外多光子解离
Fig.9 Infrared multiphoton dissociation of nucleic acids
表2 通过光电离和解离对生物分子的质谱鉴定
Table 2 Mass spectrometric identification of biological molecules with photo ionization and dissociation
Samples IR1 UV2
Principles Features Disadvantages Principles Features Disadvantages
Small organic molecules Bond cleavages by vibrational excitation Selective absorption in IR region by different bonds Need multiple IR photons to activate bond cleavages due to the low energy of each IR photon Electron/charge-directed bond cleavages + vibration excited bond cleavages Do not need multiple UV photons Extensive bond cleavages/Need chemical derivatization in the near UV light region
Monosaccharides/polysaccharides Distinguish O-, N-, C- and S- glycosidic bonds ·Characteristic a, b, y and x ions as well as neutral losses in the vacuum UV region.
Peptides/Proteins ·Characteristic b and y ions resulting from C-N bond cleavages.
·Identification of fragile posttranslational modification that is difficult in CAD3.		 ·Selective cleavages of S-S bonds in the near UV region.
·Characteristic a, x, d, v and w ions in the vacuum UV region.
·Arginine effects on the production of a or x ions
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