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Supramolecular Adducts of Cucurbit[7]uril and Amino Acids in the Gas Phase
- 作者:Ekaterina Kovalenko ; Marta Vilaseca…
- 关键词:Supramolecular chemistry ; Gas ; phase studies ; Cucurbituril ; Amino acid
- 刊名:Journal of The American Society for Mass Spectrometry
- 出版年:2016
- 出版时间:February 2016
- 年:2016
- 卷:27
- 期:2
- 页码:265-276
- 全文大小:1,083 KB
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- 作者单位:Ekaterina Kovalenko (1)
Marta Vilaseca (2) Mireia Díaz-Lobo (2) A. N. Masliy (3) Cristian Vicent (4) Vladimir P. Fedin (1)
1. Nikolaev Institute of Inorganic Chemistry, Siberian Branch of the Russian Academy of Sciences, Pr. Lavrentieva 3, 630090, Novosibirsk, Russia 2. Institute for Research in Biomedicine (IRB Barcelona), The Barcelona Institute of Science and Technology, Baldiri Reixac, 10, 08028, Barcelona, Spain 3. Kazan National Research Technological University, 420015, K.Marx St 68, Kazan, Russia 4. Serveis Centrals d’Instrumentació Científica, Universitat Jaume I, Avda. Sos Baynat s/n, E-12071, Castelló, Spain
- 刊物主题:Analytical Chemistry; Biotechnology; Organic Chemistry; Proteomics; Bioinformatics;
- 出版者:Springer US
- ISSN:1879-1123
文摘
The complexation of the macrocyclic cavitand cucurbit[7]uril (Q7) with a series of amino acids (AA) with different side chains (Asp, Asn, Gln, Ser, Ala, Val, and Ile) is investigated by ESI-MS techniques. The 1:1 [Q7 + AA + 2H]2+ adducts are observed as the base peak when equimolar Q7:AA solutions are electrosprayed, whereas the 1:2 [Q7 + 2AA + 2H]2+ dications are dominant when an excess of the amino acid is used. A combination of ion mobility mass spectrometry (IM-MS) and DFT calculations of the 1:1 [Q7 + AA + 2H]2+ (AA = Tyr, Val, and Ser) adducts is also reported and proven to be unsuccessful at discriminating between exclusion or inclusion-type conformations in the gas phase. Collision induced dissociation (CID) revealed that the preferred dissociation pathways of the 1:1 [Q7 + AA + 2H]2+ dications are strongly influenced by the identity of the amino acid side chain, whereas ion molecule reactions towards N-butylmethylamine displayed a common reactivity pattern comprising AA displacement. Special emphasis is given on the differences between the gas-phase behavior of the supramolecular adducts with amino acids (AA = Asp, Asn, Gln, Ser, Ala, Val, and Ile) and those featuring basic (Lys and Arg) and aromatic (Tyr and Phe) side chains.
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