Stapling of leu-enkephalin analogs with bifunctional reagents for prolonged analgesic activity

Kijewska, Monika; Wołczański, Grzegorz; Kosson, Piotr; Wieczorek, Robert; Lisowski, Marek; Stefanowicz, Piotr

doi:10.1039/d3cc06345c

Cited by 1 publication

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“…Furthermore, this new amino acid could be useful for peptide stapling and cyclization. The example of using its sulfur analogue, N -(2-thioethyl)glycine, for the cyclization of leu-enkephalin has been given in our recent paper . The potential synthetic application of N -(2-selenoethyl)glycine was an additional motivation to study diselenide metathesis in peptides containing this residue.…”

Section: Introductionmentioning

confidence: 99%

“…The example of using its sulfur analogue, N -(2-thioethyl)glycine, for the cyclization of leu-enkephalin has been given in our recent paper. 36 The potential synthetic application of N -(2-selenoethyl)glycine was an additional motivation to study diselenide metathesis in peptides containing this residue. Therefore, we performed studies between low-molecular-weight diselenide and both linear and cyclic peptides under visible-light irradiation, where we observed decomposition of the metathesis products that led to the formation of mono-, di-, and polyselenides.…”

Section: Introductionmentioning

confidence: 99%

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Photochemical Transformations of Peptides Containing the N-(2-Selenoethyl)glycine Moiety

Pehlivan,

Wojtkowiak,

Jezierska

et al. 2024

ACS Omega

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The diselenide bond has attracted considerable attention due to its ability to undergo the metathesis reaction in response to visible light. In our previous study, we demonstrated visible-light-induced diselenide metathesis of selenocysteine-containing linear peptides, allowing for the convenient generation of peptide libraries. Here, we investigated the transformation of linear and cyclic peptides containing the N-(2selenoethyl)glycine moiety. The linear peptides were highly susceptible to the metathesis reaction, whereas the cyclic systems gave only limited conversion yields of the metathesis product. In both cases, side reactions leading to the formation of mono-, di-, and polyselenides were observed upon prolonged irradiation. To confirm the radical mechanism of the reaction, the radical initiator 2,2′-azobis[2-(2-imidazolin-2-yl)propane] dihydrochloride (VA-044) was tested, and it was found to induce diselenide metathesis without photochemical activation. The data were interpreted in the light of quantum-chemical simulations based on density functional theory (DFT). The simulations were performed at the B3LYP-D3BJ/def2-TZVP level of theory using a continuum solvation model (IEF-PCM) and methanol as a solvent.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Photochemical Transformations of Peptides Containing the N-(2-Selenoethyl)glycine Moiety

Pehlivan,

Wojtkowiak,

Jezierska

et al. 2024

ACS Omega

Self Cite

View full text Add to dashboard Cite

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Stapling of leu-enkephalin analogs with bifunctional reagents for prolonged analgesic activity

Abstract: The design and synthesis of leu-enkephalin analogs with replaced the glycine residues by N-(2-thioethyl)glycines and opening the cyclisation potential is presented. The cyclization (stapling) was achieved using bifunctional reagents (hexafluorobenzene...

Cited by 1 publication

References 54 publications

Photochemical Transformations of Peptides Containing the N-(2-Selenoethyl)glycine Moiety

Photochemical Transformations of Peptides Containing the N-(2-Selenoethyl)glycine Moiety

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