Solid State Photo-CIDEP in Chiral Linked Systems

Magin, Ilya M.; Ivanov, Misha; Polyakov, Nikolay E.; Kruppa, Alexander I.; Fedin, Matvey V.; Leshina, Tatyana V.

doi:10.1007/s00723-021-01440-0

Cited by 1 publication

(5 citation statements)

References 22 publications

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“…In the previous section, CIDNP was used to prove stereoselectivity of ET in dyads; in this section, we discuss sensitivity of CIDNP and SS to the structure and properties of paramagnetic species with L- and D-Trp. Spin effects, specifically the chemical polarization of nuclei and electrons, have demonstrated a high sensitivity to the structure of diastereomers and their activity in photoinduced ET [ 14 , 16 ]. SS is a recently discovered property of chiral systems that appears in the difference of CIDNP enhancement coefficients (K) of ( R , S )- and ( S , S )-diastereomers under the UV irradiation [ 14 , 15 ].…”

Section: Peculiarities Of Spin Effects In Chiral Linked Systems: Expe...mentioning

confidence: 99%

“…In conclusion of this part, it should be noted that using the polarization of electrons that directly registers the paramagnetic species, BZ was also detected and the difference between ( S , S )- and ( S , R )-diastereomers of dyad II was shown [ 16 ].…”

Section: Peculiarities Of Spin Effects In Chiral Linked Systems: Expe...mentioning

confidence: 99%

“…Furthermore, many sources point to the toxic Methods of the exploration of model systems-dyads are spin chemistry (chemically induced dynamic polarization of nuclei (CIDNP) and electrons (CIDEP)) and optical spectroscopy (quenching of the fluorescence). The CIDNP and CIDEP phenomena are described everywhere, see for example [14][15][16]. Analysis of CIDNP and CIDEP effects demonstrated significant differences in the magnetic resonance characteristics of short-lived paramagnetic forms-biradical-zwitterions (BZ) of (S,S)-, (R,S)-and (S,R)-dyads, while the fluorescence data showed differences in their quenching (stereodifferentiation) [12][13][14][15][16]20].…”

Section: Introductionmentioning

confidence: 99%

“…The modified approach associated with the use of elementary photoinduced processes is described in detail in the works [ 12 , 13 , 14 ]. New approach employs model linked systems—donor-acceptor dyads, with L- or D-residues of tryptophan (Trp), which allow one to use spin effects and fluorescence quenching to study the difference in the reactivity of optical isomers in the intramolecular photoinduced electron or hydrogen atom transfer [ 15 , 16 , 17 ]. The results are compared with molecular modeling data [ 17 ].…”

Section: Introductionmentioning

confidence: 99%

“…The CIDNP and CIDEP phenomena are described everywhere, see for example [ 14 , 15 , 16 ]. Analysis of CIDNP and CIDEP effects demonstrated significant differences in the magnetic resonance characteristics of short-lived paramagnetic forms—biradical-zwitterions (BZ) of ( S , S )-, ( R , S )- and ( S , R )-dyads, while the fluorescence data showed differences in their quenching (stereodifferentiation) [ 12 , 13 , 14 , 15 , 16 , 20 ]. Molecular dynamics (MD) simulations, in turn, showed differences in the conformations of dyads with different optical configurations [ 20 ].…”

Section: Introductionmentioning

confidence: 99%

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Chiral Linked Systems as a Model for Understanding D-Amino Acids Influence on the Structure and Properties of Amyloid Peptides

Ageeva

Doktorov

Polyakov

et al. 2022

IJMS

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In this review, we provide an illustration of the idea discussed in the literature of using model compounds to study the effect of substitution of L- for D-amino acid residues in amyloid peptides. The need for modeling is due to the inability to study highly disordered peptides by traditional methods (high-field NMR, X-ray). At the same time, the appearance of such peptides, where L-amino acids are partially replaced by D-analogs is one of the main causes of Alzheimer’s disease. The review presents examples of the use diastereomers with L-/D-tryptophan in model process—photoinduced electron transfer (ET) for studying differences in reactivity and structure of systems with L- and D-optical isomers. The combined application of spin effects, including those calculated using the original theory, fluorescence techniques and molecular modeling has demonstrated a real difference in the structure and efficiency of ET in diastereomers with L-/D-tryptophan residues. In addition, the review compared the factors governing chiral inversion in model metallopeptides and Aβ42 amyloid.

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