Towards a detailed description of pyridoxamine tautomeric species

Adrover, Miquel; Caldés, Catalina; Vilanova, Bartolomé; Frau, Juan; Donoso, Josefa; Muñoz, Francisco

doi:10.1039/c2nj40230k

Cited by 8 publications

(9 citation statements)

References 44 publications

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“…Table II shows the corresponding electronic excitation energies (E exc ), their oscillator strengths (f), and the orbital transitions most markedly contributing to the excitation in each case. Consistent with previous results [37,55,56], the E exc values provided by the B3LYP functional were higher than those obtained with the HCTH functional.…”

Section: Theoretical and Experimental Study Of The Excitation Energiesupporting

confidence: 94%

“…The C3AC4AC5AC6 dihedral angles reveal that the aromatic ring loses its planarity upon excitation, consistent with previous results for similar compounds [37,50]. The distortion occurs in both S 1 and S 2 , and is especially marked in the species with a protonated O2 0 atom.…”

Section: Excited State Calculationssupporting

confidence: 86%

“…Protonation of N1 00 or O2 0 has virtually no effect on LUMO þ 1, LUMO, and HOMO; that of both groups, however, has a strong effect on HOMO À 1. Similar behavior has been described in the 4-aminomethylpyridine [37].…”

Section: Ground State Calculationssupporting

confidence: 59%

“…The theoretical results thus obtained were highly consistent with the experimental electronic excitation energies as determined from the deconvoluted UV-Vis spectra. This methodology was previously applied with success to IR spectra [36] and used recently by our group to examine electronic transitions in 4-aminomethylpyridine [37].…”

Section: Introductionmentioning

confidence: 99%

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Impact of the ionic forms on the UV–Vis spectra 2‐hydroxybenzylamine. A TD‐DFT study

Adrover¹,

Frau²,

Caldés³

et al. 2010

Int J of Quantum Chemistry

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PCM-TD-DFT computations were used to examine the electronic transitions exhibited by the molecular species of 2-hydroxybenzylamine (2-BNZ). The theoretical results thus obtained were found to accurately fit their experimental counterparts and to afford the assignation of the different experimental electronic transitions to 2-BNZ tautomers present in the solution. Also, the HCTH functional was found to accurately reproduce electronic excitations in the cationic species and neutral tautomer, and the B3LYP functional to provide accurate predictions of the transitions for the anionic species and zwitterionic tautomer.

show abstract

Section: Theoretical and Experimental Study Of The Excitation Energiesupporting

confidence: 94%

Section: Excited State Calculationssupporting

confidence: 86%

Section: Ground State Calculationssupporting

confidence: 59%

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Impact of the ionic forms on the UV–Vis spectra 2‐hydroxybenzylamine. A TD‐DFT study

Adrover¹,

Frau²,

Caldés³

et al. 2010

Int J of Quantum Chemistry

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“…Scheme 2 shows the ionic and tautomeric species for this compound. In a recent 13 C-NMR study [28], we found a to be the major tautomer for HPAM þ at pH 6.5. Equilibrium Constants for the Reactions of PM and PAM with FA.…”

mentioning

confidence: 94%

Phenol Group in Pyridoxamine Acts as a Stabilizing Element for Its Carbinolamines and Schiff Bases

Caldés

Vilanova

Adrover

et al. 2011

Chemistry & Biodiversity

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Pyridoxamine (PM), a natural derivative of vitamin B(6) , possesses a high biological and biomedical significance by virtue of its acting as enzyme cofactor in amino acid metabolism and as inhibitor in the nonenzymatic glycation of proteins. Both types of processes require the initial formation of a Schiff base. In this work, we used NMR spectroscopy to study the formation mechanism for a Schiff base between PM and formaldehyde (FA). This allowed the Schiff base and an intermediate carbinolamine (CA) to be detected. The Schiff base was found to be in isomeric equilibrium with a hemiaminal (HE) form. The formation equilibrium constants for the CA and HE over the pD range of 6.0-13.0 were determined and compared with those for the reaction between 4-picolylamine (PAM) and formaldehyde (FA). The comparison revealed a strong influence of the phenol group on the equilibrium constant. Based on the results, the phenol group in PM is a key structural element towards stabilizing the resulting carbinolamine and Schiff base.

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Extreme Carbon Dioxide Sorption Hysteresis in Open‐Channel Rigid Metal–Organic Frameworks

et al. 2015

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A systematic study is presented of three closely related microporous metal‐organic frameworks the pore dimensions of which vary according to the choice of 4,4′‐bipyridyl linker. The tunable linker allows exploration of the effect of increasing pore dimensions on the sorption behavior of the frameworks. The MOFs described capture CO2 under supercritical conditions and continue to sequester the gas under ambient conditions. Gas sorption isotherms for CO2 are compared with thermogravimetric data, and the CO2 molecules in the channels of the frameworks could be modeled using single‐crystal X‐ray diffraction analysis. Crystallographic data were used to construct a theoretical model based on DFT methods to calculate framework electrostatic potential maps with a view to understanding the nature of the sorbate–sorbent interactions.

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Towards a detailed description of pyridoxamine tautomeric species

Cited by 8 publications

References 44 publications

Impact of the ionic forms on the UV–Vis spectra 2‐hydroxybenzylamine. A TD‐DFT study

Impact of the ionic forms on the UV–Vis spectra 2‐hydroxybenzylamine. A TD‐DFT study

Phenol Group in Pyridoxamine Acts as a Stabilizing Element for Its Carbinolamines and Schiff Bases

Extreme Carbon Dioxide Sorption Hysteresis in Open‐Channel Rigid Metal–Organic Frameworks

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