Role of chiral configuration in the photoinduced interaction of d-and l-tryptophan with optical isomers of ketoprofen in linked systems

Aleksandra A. Ageeva, Ilya M. Magin, Alexander B. Doktorov, Victor F. Plyusnin, Polina S. Kuznetsova, Alexander A. Stepanov, Alexander A. Alekseev, Nikolay E. Polyakov, Tatyana V. Leshina

Результат исследования: Научные публикации в периодических изданияхстатьярецензирование

Аннотация

The study of the L-and D-amino acid properties in proteins and peptides has attracted considerable attention in recent years, as the replacement of even one L-amino acid by its D-analogue due to aging of the body is resulted in a number of pathological conditions, including Alzheimer’s and Parkinson’s diseases. A recent trend is using short model systems to study the peculiarities of proteins with D-amino acids. In this report, the comparison of the excited states quenching of Land D-tryptophan (Trp) in a model donor–acceptor dyad with (R)-and (S)-ketoprofen (KP-Trp) was carried out by photochemically induced dynamic nuclear polarization (CIDNP) and fluorescence spectroscopy. Quenching of the Trp excited states, which occurs via two mechanisms: prevailing resonance energy transfer (RET) and electron transfer (ET), indeed demonstrates some peculiarities for all three studied configurations of the dyad: (R,S)-, (S,R)-, and (S,S)-. Thus, the ET efficiency is identical for (S,R)-and (R,S)-enantiomers, while RET differs by 1.6 times. For (S,S)-, the CIDNP coefficient is almost an order of magnitude greater than for (R,S)-and (S,R)-. To understand the source of this difference, hyperpolarization of (S,S)-and (R,S)-has been calculated using theory involving the electron dipole–dipole interaction in the secular equation.

Язык оригиналаанглийский
Номер статьи6198
ЖурналInternational Journal of Molecular Sciences
Том22
Номер выпуска12
DOI
СостояниеОпубликовано - 2 июн 2021

Предметные области OECD FOS+WOS

  • 1.04 ХИМИЧЕСКИЕ НАУКИ
  • 2.04 ХИМИЧЕСКИЕ ТЕХНОЛОГИИ
  • 1.06 БИОЛОГИЧЕСКИЕ НАУКИ
  • 1.06.CQ БИОХИМИЯ И МОЛЕКУЛЯРНАЯ БИОЛОГИЯ

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