Source material and recommended further reading related to “Fluorine in Protein Chemistry: Going Where Mother Nature Deigned to Go” by Chuck Sanders.
CF2H, a Hydrogen Bond Donor
J Am Chem Soc. 2017 139:9325-9332. doi: 10.1021/jacs.7b04457. Epub 2017 Jun 27.
Chanan D Sessler, Martin Rahm , Sabine Becker, Jacob M Goldberg, Fang Wang, Stephen J Lippard
Fluorinated proteins: from design and synthesis to structure and stability.
Acc Chem Res. (2014) 47:2878-86. doi: 10.1021/ar500125m.
Marsh ENG
Principles of fluoride toxicity and the cellular response: a review.
Arch Toxicol. (2020) 94:1051-1069. doi: 10.1007/s00204-020-02687-5.
Johnston NR, Strobel SA
Membrane Exporters of Fluoride Ion.
Annu Rev Biochem. (2021) 90:559-579. doi: 10.1146/annurev-biochem-071520-112507.
McIlwain BC, Ruprecht MT, Stockbridge RB.
Deciphering the mechanistic basis for perfluoroalkyl-protein interactions.|
Lawanprasert A, Sloand JN, Vargas MG, Singh H, Eldor T, Miller MA, Pimcharoen S, Wang J, Leighow SM,.
Chembiochem (2023) e202300159. doi: 10.1002/cbic.202300159.
Pritchard JR, Dokholyan NV, Medina SH
Current perspectives of artificial oxygen carriers as red blood cell substitutes: a review of old to cutting-edge technologies using in vitro and in vivo assessments
J Pharm Investig (2023) 53:153-190. doi: 10.1007/s40005-022-00590-y.
Nijaya Mohanto, Young-Joon Park, Jun-Pil Jee
Therapeutic oxygen delivery by perfluorocarbon-based colloids.
Adv Colloid Interface Sci. (2021) 294:102407. doi: 10.1016/j.cis.2021.102407
Krafft MP, Riess JG.
Fluorine in medicinal chemistry
Chem Soc Rev. (2008) 37:320-30. doi: 10.1039/b610213c.
Sophie Purser, Peter R Moore, Steve Swallow, Véronique Gouverneur
Organic fluorine: odd man out.
Chembiochem (2004) 5:614-21. doi: 10.1002/cbic.200300801.
|Dunitz JD.
Bioorthogonal noncovalent chemistry: Fluorous phases in chemical biology
Curr Opin Chem Biol. (2006) 10:576-83. doi: 10.1016/j.cbpa.2006.10.007.
Nicholas C Yoder, Deniz Yüksel, Laila Dafik, Krishna Kumar
Trifluoroethanol and colleagues: cosolvents come of age. Recent studies with peptides and proteins.
Q Rev Biophys. (1998) 31:297-355. doi: 10.1017/s003358359800345x.
Buck M.
Fluorination Promotes the Cytosolic Delivery of Genes, Proteins, and Peptides
Acc Chem Res. (2022) 55:722-733. doi: 10.1021/acs.accounts.1c00766.
Jia Lv, Hui Wang, Guangyu Rong, Yiyun Cheng
The fluorous effect in biomolecular applications
Chem Soc Rev. (2012) 41:31-42. doi: 10.1039/c1cs15084g.
Massimo Cametti , Benoit Crousse, Pierangelo Metrangolo, Roberto Milani, Giuseppe Resnati
Small, but powerful and attractive: 19F in biomolecular NMR
Structure (2022) 30:6-14. doi: 10.1016/j.str.2021.09.009
Angela M Gronenborn
Tuning phenylalanine fluorination to assess aromatic contributions to protein function and stability in cells.
Nat Commun. (2023) 14:59. doi: 10.1038/s41467-022-35761-w.
Galles GD, Infield DT, Clark CJ, Hemshorn ML, Manikandan S, Fazan F, Rasouli A, Tajkhorshid E, Galpin JD, Cooley RB, Mehl RA, Ahern CA.
Folding of diphtheria toxin T-domain in the presence of amphipols and fluorinated surfactants: Toward thermodynamic measurements of membrane protein folding.
Biochim Biophys Acta. (2012) 1818:1006-12. doi: 10.1016/j.bbamem.2011.09.012.
Kyrychenko A, Rodnin MV, Vargas-Uribe M, Sharma SK, Durand G, Pucci B, Popot JL, Ladokhin AS.
Highly fluorinated amphiphiles and colloidal systems, and their applications in the biomedical field. A contribution.
Biochimie (1998) 80:489-514. doi: 10.1016/s0300-9084(00)80016-4.
Krafft MP, Riess JG.
Progress in the synthesis of fluorinated phosphatidylcholines for biological applications.
Gagnon MC, Auger M, Paquin JF.
Org Biomol Chem. 2018 16:4925-4941. doi: 10.1039/c8ob00991k.
Fluorinated interfaces drive self-association of transmembrane alpha helices in lipid bilayers
Angew Chem Int Ed Engl. (2006) 45:2588-91. doi: 10.1002/anie.200503567.
Natascha Naarmann 1, Başar Bilgiçer, He Meng, Krishna Kumar, Claudia Steinem
Qualitative comparison of the bilayer-associated structures of diacylglycerol and a fluorinated analog based upon oriented sample NMR data.
Chem Phys Lipids (1994) 72:41-57. doi: 10.1016/0009-3084(94)90016-7.
Sanders CR