Competing Noncovalent Host-guest Interactions and H/D Exchange: Reactions of Benzyloxycarbonyl-Proline Glycine Dipeptide Variants with ND3

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• 作者：Mahsan Miladi ; Abayomi D. Olaitan…
• 关键词：Ion mobility ; Host ; guest ; H/D exchange ; Adduct formation ; Ion ; molecule reactions
• 刊名：Journal of The American Society for Mass Spectrometry
• 出版年：2015
• 出版时间：November 2015
• 年：2015
• 卷：26
• 期：11
• 页码：1938-1949
• 全文大小：1,154 KB
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• 作者单位：Mahsan Miladi (1)
  Abayomi D. Olaitan (1)
  Behrooz Zekavat (1)
  Touradj Solouki (1)
  
  1. Department of Chemistry and Biochemistry, Baylor University, Waco, TX, 76706, USA
  
• 刊物主题：Analytical Chemistry; Biotechnology; Organic Chemistry; Proteomics; Bioinformatics;
• 出版者：Springer US
• ISSN：1879-1123

文摘

A combination of density functional theory calculations, hydrogen/deuterium exchange (HDX) reactions, ion mobility-mass spectrometry, and isotope labeling tandem mass spectrometry was used to study gas-phase “host–guest-type interactions of a benzyloxycarbonyl (Z)-capped proline (P) glycine (G) model dipeptide (i.e., Z-PG) and its various structural analogues with ND₃. It is shown that in a solvent-free environment, structural differences between protonated and alkali metal ion (Na+, K+, or Cs+)-complexed species of Z-PG affect ND₃ adduct formation. Specifically, [Z-PG + H]+ and [Z-PG-OCH₃ + H]+ formed gas-phase ND₃ adducts ([Z-PG (or Z-PG-OCH₃) + H + ND₃]+) but no ND₃ adducts were observed for [Z-PG + alkali metal]+ or [Z-PG + H -CO₂]+. Experimentally measured and theoretically calculated collision cross sections (CCSs) of protonated and alkali metal ion-complexed Z-PG species showed similar trends that agreed with the observed structural differences from molecular modeling results. Moreover, results from theoretical ND₃ affinity calculations were consistent with experimental HDX observations, indicating a more stable ND₃ adduct for [Z-PG + H]+ compared to [Z-PG + alkali metal]+ species. Molecular modeling and experimental MS results for [Z-PG + H]+ and [Z-PG + alkali metal]+ suggest that optimized cation–π and hydrogen bonding interactions of carbonyl groups in final products are important for ND₃ adduct formation.