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Amide-imide tautomerization presents a pervasive class of chemical transformations in organic chemistry of natural compounds. In this Perspective, we describe two distinctively different protein systems, in which the amide-imide tautomerization in the glutamine side chain takes place in enzymatic or photochemical reactions. First, hydrolysis of guanosine triphosphate (GTP) catalyzed by the Ras-GAP protein complex suggests the occurrence of the imide tautomer of glutamine in reaction intermediates. Second, photoexcitation of flavin-binding protein domains (BLUFs) initiates a chain of reactions in the chromophore-binding pocket, including amide-imide tautomerization of glutamine. Mechanisms of these reactions at the atomic level have been revealed in quantum mechanics/molecular mechanics (QM/MM) simulations. To reinforce conclusions on the critical role of amide-imide tautomerization of glutamine in these reactions we describe results of new quantum chemistry and QM/MM calculations for relevant molecular model systems. We reexamine results of the recent IR spectroscopy studies of BLUF domains, which provide experimental evidences of Gln tautomerization in proteins. We also propose to validate the glutamine-assisted mechanism of enzymatic GTP hydrolysis by using IR spectroscopy in a proper range of wavenumbers.
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http://dx.doi.org/10.1039/c8cp04817g | DOI Listing |
ACS Appl Mater Interfaces
October 2021
Functional Materials Division, Materials & Manufacturing Directorate, Air Force Research Laboratory, AFRL/RXA, Wright-Patterson Air Force Base, Ohio 45433-7750, United States.
To discern multiple intertwined effects, a set of azobenzene-functionalized amide-imide block copolymers, azo(PA--PI)-, where is amide-block content, ., [azoPA] = 25, 50, 75 mol %, was synthesized from 2,2-bis{4-[4-(4-aminophenyldiazenyl)phenoxy]phenyl}propane(azoBPA), 4,4'-oxydibenzoyl chloride (ODBC), and 4,4'-oxydiphthalic anhydride (OPDA). Including homopolymers (azoPA and azoPI), this series of amorphous azopolymers possesses a high glass-transition temperature ( > 210 °C) and a modulus (' ∼ 1.
View Article and Find Full Text PDFColloids Surf B Biointerfaces
October 2019
Institute of Physics, University of Silesia, 75 Pulku Piechoty 1, 41-500 Chorzow, Poland; Silesian Center for Education and Interdisciplinary Research, 75 Pulku Piechoty 1a, 41-500 Chorzow, Poland.
The uniform thin films with variable thicknesses (d = 49, 120, 220 nm) of active pharmaceutical ingredient (API) glibenclamide (GCM) was spin-coated and investigated using broadband dielectric, grazing incident FTIR spectroscopies, atomic force microscopy, and ellipsometry. Data analysis revealed that nanoconfined systems consist of a mixture of amide and imidic acid forms of this pharmaceutical, wherein the ratios of both tautomeric forms in the thin films were different with respect to the molten supercooled bulk system. Moreover, changes in the populations of glibenclamide tautomers, i.
View Article and Find Full Text PDFPhys Chem Chem Phys
October 2018
Department of Chemistry, Lomonosov Moscow State University, Leninskie Gory 1/3, 119991 Moscow, Russian Federation.
Amide-imide tautomerization presents a pervasive class of chemical transformations in organic chemistry of natural compounds. In this Perspective, we describe two distinctively different protein systems, in which the amide-imide tautomerization in the glutamine side chain takes place in enzymatic or photochemical reactions. First, hydrolysis of guanosine triphosphate (GTP) catalyzed by the Ras-GAP protein complex suggests the occurrence of the imide tautomer of glutamine in reaction intermediates.
View Article and Find Full Text PDFChemosphere
July 2016
Department of Sciences and Technological Innovation, University of Eastern Piedmont A. Avogadro, 51121 Alessandria, Italy.
The adsorption efficiency of a high silica zeolite Y towards sulfamethoxazole, a sulfonamide antibiotic, was evaluated in the presence of two humic monomers, vanillin and caffeic acid, representative of phenolic compounds usually occurring in water bodies, owing their dimension comparable to those of the zeolite microporosity. In the entire range of investigated pH (5-8), adsorption of vanillin, as a single component, was reversible whereas it was irreversible for sulfamethoxazole. In equimolar ternary mixtures, vanillin coadsorbed with sulfamethoxazole, conversely to what observed for caffeic acid, accordingly to their adsorption kinetics and pKa values.
View Article and Find Full Text PDFActa Crystallogr Sect E Struct Rep Online
January 2014
Department of Chemistry, NITK Surathkal, Mangalore 575 025, India.
In the crystal structure of the title compound, C7H5NO4·C9H9N3O2S2, the sulfa-thia-zole and 4-nitro-benzoic acid mol-ecules are held together by short π-π contacts between the thia-zole and nitro-benzene rings, with a centroid-centroid distance of 3.8226 (7) Å. The sulfa-thia-zole mol-ecules form dimers via N-H⋯N hydrogen bonds involving the thia-zole and sulfonamide moieties, owing to the fact that sulfathizole exhibits amide-imide tautomerism.
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