Literature DB >> 31410655

Chiral Differentiation of Non-Covalent Diastereomers Based on Multichannel Dissociation Induced by 213-nm Ultraviolet Photodissociation.

Yingying Shi1, Min Zhou1,2, Kailin Zhang1,3, Lifu Ma3, Xianglei Kong4,5.   

Abstract

Here we present the implementation of 213-nm ultraviolet photodissociation (UVPD) in a FT-ICR mass spectrometer for chiral differentiation in the gas phase. The L/D amino acid-substituted serine octamer ions were selected as examples of diastereoisomers for chiral analysis. Several kinds of fragment ions were observed in these experiments, including fragment ions that are similar to the ones observed in corresponding collision-activated dissociation (CAD) experiments, fragment ions generated with different protonation sites by only destroying non-covalent bonds, and unique non-covalent cluster radical ions. The latter two kinds of fragment ions are found to be more sensitive to the chirality of the substituted units. Further experiments suggest that the formation of radical ions is mainly affected by chromophores on side chains of the substituted units and micro surroundings of the characterized non-covalent diastereoisomers. A comparing experiment performed by only changing the wavelength of UV laser to 266 nm shows that the 213-nm UV laser has the priority in the diversity of fragmentation pathways and potential of further application in chiral differentiation experiments.

Entities:  

Keywords:  Amino acids; Chiral differentiation; Fragmentation pathways; Radical ions; Serine octamer; Ultraviolet photodissociation

Year:  2019        PMID: 31410655     DOI: 10.1007/s13361-019-02302-7

Source DB:  PubMed          Journal:  J Am Soc Mass Spectrom        ISSN: 1044-0305            Impact factor:   3.109


  54 in total

Review 1.  Chiral analysis by MS.

Authors:  W Andy Tao; R Graham Cooks
Journal:  Anal Chem       Date:  2003-01-01       Impact factor: 6.986

2.  Chiral melamine derivatives: design, synthesis, and application to mass spectrometry-based chiral analysis.

Authors:  Qin Liu; Shuzhen Zhang; Bidong Wu; Jifen Guo; Jianwei Xie; Mingsong Gu; Yimin Zhao; Liuhong Yun; Keliang Liu
Journal:  Anal Chem       Date:  2005-08-15       Impact factor: 6.986

3.  Characterization of neutral fragments issued from the photodissociation of protonated tryptophane.

Authors:  V Lepère; B Lucas; M Barat; J A Fayeton; Y J Picard; C Jouvet; P Carçabal; I Nielsen; C Dedonder-Lardeux; G Grégoire; A Fujii
Journal:  Phys Chem Chem Phys       Date:  2007-08-08       Impact factor: 3.676

4.  Side chain chemistry mediates backbone fragmentation in hydrogen deficient peptide radicals.

Authors:  Qingyu Sun; Hosea Nelson; Tony Ly; Brian M Stoltz; Ryan R Julian
Journal:  J Proteome Res       Date:  2009-02       Impact factor: 4.466

5.  Mechanisms of photoinduced Calpha[Single Bond]Cbeta bond breakage in protonated aromatic amino acids.

Authors:  B Lucas; M Barat; J A Fayeton; M Perot; C Jouvet; G Grégoire; S Brondsted Nielsen
Journal:  J Chem Phys       Date:  2008-04-28       Impact factor: 3.488

6.  Enantiomeric Excess Determination for Monosaccharides Using Chiral Transmission to Cold Gas-Phase Tryptophan in Ultraviolet Photodissociation.

Authors:  Akimasa Fujihara; Naoto Maeda; Thuc N Doan; Shigeo Hayakawa
Journal:  J Am Soc Mass Spectrom       Date:  2016-10-13       Impact factor: 3.109

7.  Molecular recognition and quantitative analysis of leucine and isoleucine using photodissociation of cold gas-phase noncovalent complexes.

Authors:  Narumi Oki; Akimasa Fujihara
Journal:  J Mass Spectrom       Date:  2018-07       Impact factor: 1.982

8.  Kinetic Resolution of d,l-Amino Acids Based on Gas-Phase Dissociation of Copper(II) Complexes.

Authors:  W A Tao; D Zhang; F Wang; P D Thomas; R G Cooks
Journal:  Anal Chem       Date:  1999-10-01       Impact factor: 6.986

9.  Infrared spectrum and structure of the homochiral serine octamer-dichloride complex.

Authors:  Jongcheol Seo; Stephan Warnke; Kevin Pagel; Michael T Bowers; Gert von Helden
Journal:  Nat Chem       Date:  2017-07-10       Impact factor: 24.427

10.  213 nm Ultraviolet Photodissociation on Peptide Anions: Radical-Directed Fragmentation Patterns.

Authors:  Mohammad A Halim; Marion Girod; Luke MacAleese; Jérôme Lemoine; Rodolphe Antoine; Philippe Dugourd
Journal:  J Am Soc Mass Spectrom       Date:  2015-11-06       Impact factor: 3.109

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  1 in total

Review 1.  Application of Infrared Multiple Photon Dissociation (IRMPD) Spectroscopy in Chiral Analysis.

Authors:  Yingying Shi; Mengying Du; Juan Ren; Kailing Zhang; Yicheng Xu; Xianglei Kong
Journal:  Molecules       Date:  2020-11-05       Impact factor: 4.411

  1 in total

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