Hydrolysis, polarity, and conformational impact of C-terminal partially fluorinated ethyl esters in peptide models

Scholarly Works

• Barata-Vallejo, S.; Bonesi, S. M.; Postigo, A. Advances in Direct Fluoroalkylation of Organic Substrates with Partially Fluorinated Alkyl Motivs. ACS Catalysis 2024, 14, 15879–15907. doi:10.1021/acscatal.4c04986
• Kubyshkin, V.; Rubini, M. Proline Analogues. Chemical reviews 2024, 124, 8130–8232. doi:10.1021/acs.chemrev.4c00007
• Kubyshkin, V. Application of (4R)-aminoproline in peptide engineering: conformational bias and pH-responsiveness revisited. New Journal of Chemistry 2022, 46, 9587–9594. doi:10.1039/d2nj00305h
• Kubyshkin, V.; Bürck, J.; Babii, O.; Budisa, N.; Ulrich, A. S. Remarkably high solvatochromism in the circular dichroism spectra of the polyproline-II conformation: limitations or new opportunities?. Physical chemistry chemical physics : PCCP 2021, 23, 26931–26939. doi:10.1039/d1cp04551b
• Kubyshkin, V. Experimental lipophilicity scale for coded and noncoded amino acid residues. Organic & biomolecular chemistry 2021, 19, 7031–7040. doi:10.1039/d1ob01213d
• Jeffries, B.; Wang, Z.; Troup, R. I.; Goupille, A.; Le Questel, J.-Y.; Fallan, C.; Scott, J. S.; Chiarparin, E.; Graton, J.; Linclau, B. Lipophilicity trends upon fluorination of isopropyl, cyclopropyl and 3-oxetanyl groups. Beilstein journal of organic chemistry 2020, 16, 2141–2150. doi:10.3762/bjoc.16.182
• Ochkhikidze, N.; Titvinidze, G.; Gverdtsiteli, M.; Otinashvili, G.; Tugushi, D.; Katsarava, R. Synthesis of AABB-polydepsipeptides, poly(ester amide)s and functional polymers on the basis of O,O′-diacyl-bis-glycolic acids. Journal of Macromolecular Science, Part A 2020, 57, 854–864. doi:10.1080/10601325.2020.1800411
• Muchowska, K. B.; Pascoe, D. J.; Borsley, S.; Smolyar, I. V.; Mati, I. K.; Adam, C.; Nichol, G. S.; Ling, K. B.; Cockroft, S. L. Reconciling Electrostatic and n→π* Orbital Contributions in Carbonyl Interactions. Angewandte Chemie 2020, 132, 14710–14716. doi:10.1002/ange.202005739
• Muchowska, K. B.; Pascoe, D. J.; Borsley, S.; Smolyar, I. V.; Mati, I. K.; Adam, C.; Nichol, G. S.; Ling, K.; Cockroft, S. L. Reconciling Electrostatic and n→π* Orbital Contributions in Carbonyl Interactions. Angewandte Chemie (International ed. in English) 2020, 59, 14602–14608. doi:10.1002/anie.202005739
• Jeffries, B.; Wang, Z.; Felstead, H. R.; Le Questel, J.-Y.; Scott, J. S.; Chiarparin, E.; Graton, J.; Linclau, B. Systematic Investigation of Lipophilicity Modulation by Aliphatic Fluorination Motifs. Journal of medicinal chemistry 2020, 63, 1002–1031. doi:10.1021/acs.jmedchem.9b01172
• Levi, N.; Amir, D.; Gershonov, E.; Zafrani, Y. Recent Progress on the Synthesis of CF2H-Containing Derivatives. Synthesis 2019, 51, 4549–4567. doi:10.1055/s-0039-1690027
• Kubyshkin, V.; Budisa, N. Promotion of the collagen triple helix in a hydrophobic environment. Organic & biomolecular chemistry 2019, 17, 2502–2507. doi:10.1039/c9ob00070d
• León, I.; Alonso, E. R.; Cabezas, C.; Mata, S.; Alonso, J. L. Unveiling the n→π* interactions in dipeptides. Communications Chemistry 2019, 2, 1–8. doi:10.1038/s42004-018-0103-2
• Kubyshkin, V.; Pridma, S. O.; Budisa, N. Comparative effects of trifluoromethyl- and methyl-group substitutions in proline. New Journal of Chemistry 2018, 42, 13461–13470. doi:10.1039/c8nj02631a
• Kubyshkin, V.; Budisa, N. Exploring hydrophobicity limits of polyproline helix with oligomeric octahydroindole-2-carboxylic acid. Journal of peptide science : an official publication of the European Peptide Society 2018, 24, e3076. doi:10.1002/psc.3076

Explore citations to this article at