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Progress in Chemistry 2021, Vol. 33 Issue (12): 2316-2333 DOI: 10.7536/PC201123 Previous Articles   Next Articles

• Review •

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: Revised: Online: Published:
  • Contact: Hongying Zhong
  • Supported by:
    the National Natural Science Foundation of China(21834002)
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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
Fig.1 Dissociation pathways of peptides. (A) Chemical bond cleavages and resulting characteristic fragment ions; (B) representative dissociation techniques and instruments
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
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
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
Fig.4 Ultraviolet photo ionization and characteristic neutral losses of three aromatic amino acids
Fig.5 Mechanisms of infrared multiphoton dissociation of drugs and biological small molecules. (A) Cephalosporins,(B) Penicillin, (C) Chlorophyl
Fig.6 Infrared multiphoton dissociation of monosaccharides and polysaccharides. (A) Erythromycin, (B) Neomycin
Fig.7 Ultraviolet photo dissociation of oligosaccharides
Fig.8 Vacuum ultraviolet photo dissociation of peptides/proteins
Fig.9 Infrared multiphoton dissociation of nucleic acids
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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