Anhydrous monoalkylguanidines in aprotic and nonpolar solvents: models for deprotonated arginine side chains in membrane environments

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dc.contributor.authorBanyikwa, Andrew Toyi
dc.contributor.authorMiller, Stephen E.
dc.contributor.authorKrebs, Richard A.
dc.contributor.authorXiao, Yuewu
dc.contributor.authorCarney, Jeffrey M.
dc.contributor.authorBraiman, Mark S.
dc.date.accessioned2020-11-24T08:33:27Z
dc.date.available2020-11-24T08:33:27Z
dc.date.issued2017
dc.descriptionFull text article. Also available at https://doi.org/10.1021/acsomega.7b00281en_US
dc.description.abstractIn this study, the synthesis of crystalline dodecylguanidine free base and its spectroscopic characterization in nonpolar environments are described. IR as well as 1H and 15N NMR spectra of the free base dissolved in aprotic solvents are substantially different from the previously reported spectra of arginine, or other monoalkylguanidinium compounds, at high hydroxide concentrations. The current results provide improved modeling for the spectroscopic signals that would be expected from a deprotonated arginine in a nonpolar environment. On the basis of our spectra of the authentic dodecylguanidine free base, addition of large amounts of aqueous hydroxide to arginine or other monoalklyguanidinium salts does not deprotonate them. Instead, hydroxide addition leads to the formation of a guanidinium hydroxide complex, with a dissociation constant near ∼500 mM that accounts for the established arginine pK value of ∼13.7. We also report a method for synthesizing a compound containing both phenol and free-base guanidine groups, linked by a dodecyl chain that should be generalizable to other hydrocarbon linkers. Such alkyl-guanidine and phenolyl-alkyl-guanidine compounds can serve as small-molecule models for the conserved arginine–tyrosine groupings that have been observed in crystallographic structures of both microbial rhodopsins and G-protein-coupled receptors.en_US
dc.identifier.citationBanyikwa, A. T., Miller, S. E., Krebs, R. A., Xiao, Y., Carney, J. M., & Braiman, M. S. (2017). Anhydrous monoalkylguanidines in aprotic and nonpolar solvents: Models for deprotonated arginine side chains in membrane environments. ACS Omega, 2(10), 7239-7252.en_US
dc.identifier.otherDOI: 10.1021/acsomega.7b00281
dc.identifier.urihttp://hdl.handle.net/20.500.12661/2517
dc.language.isoenen_US
dc.publisherACS Publicationsen_US
dc.subjectCrystalline dodecylguanidineen_US
dc.subjectEnvironmentsen_US
dc.subjectAnhydrous monoalkylguanidinesen_US
dc.subjectMonoalkylguanidinium compoundsen_US
dc.subjectGuanidinium hydroxide complexen_US
dc.subjectMicrobial rhodopsinsen_US
dc.subjectDeprotonated arginineen_US
dc.subjectNonpolar solventsen_US
dc.subjectAprotic solventsen_US
dc.subjectMembraneenvironmenten_US
dc.subjectArginineen_US
dc.subjectAlkylguanidinium bromideen_US
dc.subjectArginine side chainen_US
dc.titleAnhydrous monoalkylguanidines in aprotic and nonpolar solvents: models for deprotonated arginine side chains in membrane environmentsen_US
dc.typeArticleen_US
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