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Analysis of the isomerization of diketopiperazine consisting of proline and aromatic amino acid residues using nuclear magnetic resonance

Analytical science advances, 2022-02, Vol.3 (1-2), p.38-46 [Peer Reviewed Journal]

2021 The Authors. Analytical Science Advances published by Wiley‐VCH GmbH. ;2022. This work is published under http://creativecommons.org/licenses/by-nc-nd/4.0/ (the “License”). Notwithstanding the ProQuest Terms and Conditions, you may use this content in accordance with the terms of the License. ;2021 The Authors. published by Wiley‐VCH GmbH ;ISSN: 2628-5452 ;EISSN: 2628-5452 ;DOI: 10.1002/ansa.202100047 ;PMID: 38716055

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  • Title:
    Analysis of the isomerization of diketopiperazine consisting of proline and aromatic amino acid residues using nuclear magnetic resonance
  • Author: Ishizu, Takashi ; Sato, Popuri ; Tsuyama, Shiori ; Nagao, Ryosuke ; Fujiki, Kanae ; Yamaji, Amia
  • Subjects: Amino acids ; Full ; Hydrocarbons ; Magnetic fields ; NMR ; Nuclear magnetic resonance ; Peptides
  • Is Part Of: Analytical science advances, 2022-02, Vol.3 (1-2), p.38-46
  • Description: Under different concentrations of the base potassium deuteroxide KOD, the progress of reactions, such as enolization, D-substitution, isomerization, and conformational changes of diketopiperazine cyclo(L-Pro-L-Xxx) and cyclo(D-Pro-L-Xxx) (Xxx = Phe, Tyr) in D O solution, was investigated by H nuclear magnetic resonance (NMR). Cyclo(L-Pro-L-Xxx) is mostly isomerized to cyclo(D-Pro-L-Xxx) in D O solution, whereas cyclo(D-Pro-L-Xxx) is only slightly isomerized to cyclo(L-Pro-L-Xxx) even under stronger basic conditions. After adding a deuterated organic solvent (CD COCD , CD SOCD or CD OD) to a D O solution of cyclo(L-Pro-L-Xxx), cyclo(D-Pro-L-Xxx), or increasing the temperature of the D O solution, CH-π interaction between H and the benzene ring of cyclo (D-Pro-L-Xxx) was stronger than that between H and the benzene ring of cyclo(L-Pro-L-Xxx).
  • Publisher: Germany: John Wiley & Sons, Inc
  • Language: English
  • Identifier: ISSN: 2628-5452
    EISSN: 2628-5452
    DOI: 10.1002/ansa.202100047
    PMID: 38716055
  • Source: AUTh Library subscriptions: ProQuest Central
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