Biochemistry of fluoroprolines: the prospect of making fluorine a bioelement

Scholarly Works

• Kubyshkin, V.; Mykhailiuk, P. K. Proline Analogues in Drug Design: Current Trends and Future Prospects. Journal of Medicinal Chemistry 2024. doi:10.1021/acs.jmedchem.4c01987
• Karbalaei-Heidari, H. R.; Budisa, N. Advanced and Safe Synthetic Microbial Chassis with Orthogonal Translation System Integration. ACS synthetic biology 2024, 13, 2992–3002. doi:10.1021/acssynbio.4c00437
• Kubyshkin, V.; Rubini, M. Proline Analogues. Chemical reviews 2024, 124, 8130–8232. doi:10.1021/acs.chemrev.4c00007
• Nieto-Domínguez, M.; Sako, A.; Enemark-Rasmussen, K.; Gotfredsen, C. H.; Rago, D.; Nikel, P. I. Enzymatic synthesis of mono- and trifluorinated alanine enantiomers expands the scope of fluorine biocatalysis. Communications chemistry 2024, 7, 104. doi:10.1038/s42004-024-01188-1
• Ganguly, H. K.; Ludwig, B. A.; Tressler, C. M.; Bhatt, M. R.; Pandey, A. K.; Quinn, C. M.; Bai, S.; Yap, G. P. A.; Zondlo, N. J. 4,4-Difluoroproline as a Unique 19F NMR Probe of Proline Conformation. Biochemistry 2024, 63, 1131–1146. doi:10.1021/acs.biochem.3c00697
• Loughlin, J. O.; Zinovjev, K.; Napolitano, S.; van der Kamp, M.; Rubini, M. 4-Thiaproline accelerates the slow folding phase of proteins containing cis prolines in the native state by two orders of magnitude. Protein science : a publication of the Protein Society 2024, 33, e4877. doi:10.1002/pro.4877
• Nieto-Dominguez, M.; Sako, A.; Enemark-Rasmussen, K.; Gotfredsen, C. H.; Rago, D.; Nikel, P. I. High-yield enzymatic synthesis of mono– and trifluorinated alanine enantiomers. Cold Spring Harbor Laboratory 2023. doi:10.1101/2023.11.28.569005
• Karbalaei-Heidari, H. R.; Budisa, N. Genomically integrated orthogonal translation inEscherichia coli, a new synthetic auxotrophic chassis with altered genetic code, genetic firewall, and enhanced protein expression. Cold Spring Harbor Laboratory 2023. doi:10.1101/2023.11.18.567690
• Goettig, P.; Koch, N. G.; Budisa, N. Non-Canonical Amino Acids in Analyses of Protease Structure and Function. International journal of molecular sciences 2023, 24, 14035. doi:10.3390/ijms241814035
• Miles, S. A.; Nillama, J. A.; Hunter, L. Tinker, Tailor, Soldier, Spy: The Diverse Roles That Fluorine Can Play within Amino Acid Side Chains. Molecules (Basel, Switzerland) 2023, 28, 6192. doi:10.3390/molecules28176192
• O' Loughlin, J.; Zinovjev, K.; Napolitano, S.; van der Kamp, M.; Rubini, M. 4-Thiaproline accelerates the slow folding phase of proteins containingcisprolines in the native state by two orders of magnitude. Cold Spring Harbor Laboratory 2023. doi:10.1101/2023.06.23.546227
• Li, Y.; Lu, D.; Gong, Y. Cu-catalysed three-component C–H trifluoroalkylation of glycine derivatives: access to diverse CF3-containing amino acids. Organic Chemistry Frontiers 2023, 10, 2301–2309. doi:10.1039/d3qo00267e
• Chernykh, A. V.; Aloshyn, D.; Kuchkovska, Y. O.; Daniliuc, C. G.; Tolmachova, N. A.; Kondratov, I. S.; Zozulya, S.; Grygorenko, O. O.; Haufe, G. Impact of β-perfluoroalkyl substitution of proline on the proteolytic stability of its peptide derivatives. Organic & biomolecular chemistry 2022, 20, 9337–9350. doi:10.1039/d2ob01430k
• Mykhailiuk, P. K. Fluorine-Containing Prolines: Synthetic Strategies, Applications, and Opportunities. The Journal of organic chemistry 2022, 87, 6961–7005. doi:10.1021/acs.joc.1c02956
• Mardirossian, M.; Rubini, M.; Adamo, M. F. A.; Scocchi, M.; Saviano, M.; Tossi, A.; Gennaro, R.; Caporale, A. Natural and Synthetic Halogenated Amino Acids-Structural and Bioactive Features in Antimicrobial Peptides and Peptidomimetics. Molecules (Basel, Switzerland) 2021, 26, 7401. doi:10.3390/molecules26237401
• Sinnaeve, D.; Bouzayene, A. B.; Ottoy, E.; Hofman, G.-J.; Erdmann, E.; Linclau, B.; Kuprov, I.; Martins, J. C.; Torbeev, V. Y.; Kieffer, B. Fluorine NMR study of proline-rich sequences using fluoroprolines. Magnetic resonance (Gottingen, Germany) 2021, 2, 795–813. doi:10.5194/mr-2-795-2021
• Loughlin, J. O.; Napolitano, S.; Rubini, M. Protein Design with Fluoroprolines: 4,4-Difluoroproline Does Not Eliminate the Rate-Limiting Step of Thioredoxin Folding. Chembiochem : a European journal of chemical biology 2021, 22, 3326–3332. doi:10.1002/cbic.202100418
• Zhu, Z.; Krishnamurti, V.; Ispizua-Rodriguez, X.; Barrett, C.; Prakash, G. K. S. Chemoselective N- and O-Difluoromethylation of 2-Pyridones, Isoquinolinones, and Quinolinones with TMSCF2Br. Organic letters 2021, 23, 6494–6498. doi:10.1021/acs.orglett.1c02305
• Kubyshkin, V. Experimental lipophilicity scale for coded and noncoded amino acid residues. Organic & biomolecular chemistry 2021, 19, 7031–7040. doi:10.1039/d1ob01213d

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