IR spectra of guanine and hypoxanthine isolated molecules

Sheina, G. G.; Stepanian, S. G.; Radchenko, E. D.; Blagoı̆, Yu. P.

doi:10.1016/0022-2860(87)80024-8

Cited by 151 publications

(108 citation statements)

References 17 publications

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“…The vibrational spectra of guanine and hypoxanthine as well as their respective nucleosides and nucleotides have been published and discussed previously (Psoda & Shugar, 1971;Lane & Thomas, 1979;Ferreira & Thomas, 1981;Majoube, 1985;Sheina et al, 1987;Lagant et al, 1991). However, we show solution data of GDP and IDP for reference as well as those for 6-thio-GDP in Figure 2, and we follow the previous spectral assignments in our discussion below.…”

Section: Nucleotide Spectroscopysupporting

confidence: 73%

Hydrogen bond interactions of G proteins with the guanine ring moiety of guanine nucleotides

et al. 1994

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We have utilized Raman difference spectroscopy to investigate hydrogen bonding interactions of the guanine moiety in guanine nucleotides with the binding site of two G proteins, EF-Tu (elongation factor Tu from Escherichia colt) and the c-Harvey rus protein, p21 (the gene product of the human c-H-rus proto-oncogene). Raman spectra of proteins complexed with GDP (guanosine 5' diphosphate), IDP (inosine 5' diphosphate), 6-thio-GDP, and 6-'*O-GDP were measured, and the various difference spectra were determined. These were compared to the difference spectra obtained in solution, revealing vibrational features of the nucleotide that are altered upon binding. Specifically, we observed significant frequency shifts in the vibrational modes associated with the 6-keto and 2-amino positions of the guanine group of GDP and IDP that result from hydrogen bonding interactions between these groups and the two proteins. These shifts are interpreted as being proportional to the local energy of interaction ( A H ) between the two groups and protein residues at the nucleotide binding site. Consistent with the tight binding between the nucleotides and the two proteins, the shifts indicate that the enthalpic interactions are stronger between these two polar groups and protein than with water. In general, the spectral shifts provide a rationale for the stronger binding of GDP and IDP with p21 compared to EF-Tu. Despite the structural similarity of the binding sites of EF-Tu and p21, the strengths of the observed hydrogen bonds at the 6-keto and 2-amino positions vary substantially, by up to a factor of 2. The hydrogen bond between the protein and the 6-keto group is stronger for GDP in EF-Tu compared to p21, but this comparison is reversed for bound IDP. Thus, the removal of the 2-amino group from GDP to form IDP affects binding properties distal to the amino site.Keywords: EF-Tu; G proteins; hydrogen bonding; nucleotide binding; p21; Raman spectroscopy A variety o f key cellular processes such as signal transduction, protein transport, and protein biosynthesis are regulated in vivo by members of the guanine nucleotide binding protein (also termed GTPase) superfamily. These proteins share strong functional and structural homologies (for reviews, see Masters et al., 1986;Wooley & Clark, 1989;Bourne et al., 1990Bourne et al., , 1991, and their biochemical activities are tightly regulated by the nature of the bound nucleotide. In general, they are biochemically active ("on") in the GTP-bound form, and their internal GTPase

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Section: Nucleotide Spectroscopysupporting

confidence: 73%

Hydrogen bond interactions of G proteins with the guanine ring moiety of guanine nucleotides

et al. 1994

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“…The first experimental observation of amino-keto and amino-enol tautomeric forms of Gua has been performed on isolated species in cold inert gas matrix by ground state infrared spectroscopy (Sheina et al, 1987;Szczepaniak & Szczesniak, 1987). By using UV-UV, IR-UV hole burning (Nir et al, 2001b(Nir et al, , 2002b and resonance-enhanced multiphoton ionization (REMPI) (Nir et al, 1999(Nir et al, , 2002b spectroscopy, de Vries and co-workers found spectral 70 features that they assigned to the N9H keto, N7H keto, and N9H enol (cis-or trans-) forms.…”

Section: Mutagenic Tautomers Of Dna Basesmentioning

confidence: 99%

“…But evidence for these types of tautomeric shifts remains sparse, because the limited sensitivity of the experimental methods prevents an accurate detection of the relative amount of the rare tautomers including mutagenic. Among all rare tautomers, only the imino tautomers of Cyt (Brown et al, 1989b;Dreyfus et al, 1976;Feyer et al, 2010;Szczesniak et al, 1988) and enol tautomers of Gua (Choi & Miller, 2006;Sheina et al, 1987;Plekan et al, 2009;Szczepaniak & Szczesniak, 1987) were experimentally detected. The lack of the experimental data on the rare tautomers of Ade (Brown et al, 1989a) and Thy can be explained by the high value of their relative energy (~12÷14 kcal/mol at 298.15 K) estimated by theoretical investigations (Basu et al, 2005;Brovarets' & Hovorun, 2010a;Fonseca Guerra et al, 2006;Mejía-Mazariegos & Hernández-Trujillo, 2009;Samijlenko et al, 2000Samijlenko et al, , 2004.…”

Section: Introductionmentioning

confidence: 99%

Elementary Molecular Mechanisms of the Spontaneous Point Mutations in DNA: A Novel Quantum-Chemical Insight into the Classical Understanding

Brovarets’¹,

Kolomiets²,

Hovorun³

2012

Quantum Chemistry - Molecules for Innovations

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“…In a wide variety of environments, including the gas phase, keto tautomers of hypoxan thine are most stable. This conclusion is supported by results of UV 19,21 , IR 17,18 , Raman 29 , 1H NMR 19 and 13C NMR 19,23 spectroscopies, and X-ray analysis 24 . Pullman and Pullman 28 have investigated the tautomerism of oxopurines by the theoretical CNDO/2 method and three groups of authors [29][30][31] have reported ab initio quantum mechanical calculations using 6-31G(d), 6-31G(d,p), or MIDI basis sets.…”

mentioning

confidence: 55%

“…In addition, knowing how these tautomerization energies change in different environments can provide insight into the influence of solvent effects on molecular stability. The physicochemical properties of the tautomerism of hypoxanthine have been investigated experimentally [17][18][19][20][21][22][23][24][25][26][27] and theoretically [28][29][30][31][32] . In a wide variety of environments, including the gas phase, keto tautomers of hypoxan thine are most stable.…”

mentioning

confidence: 99%

A DFT Study of Solvation Effects on Tautomerism of 6-oxo Purine by Polarisable Continuum Method (PCM)

Heidarnezhad¹,

Heidarnezhad²,

Heydari³

et al. 2013

Orientjchem.

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IR spectra of guanine and hypoxanthine isolated molecules

Cited by 151 publications

References 17 publications

Hydrogen bond interactions of G proteins with the guanine ring moiety of guanine nucleotides

Hydrogen bond interactions of G proteins with the guanine ring moiety of guanine nucleotides

Elementary Molecular Mechanisms of the Spontaneous Point Mutations in DNA: A Novel Quantum-Chemical Insight into the Classical Understanding

A DFT Study of Solvation Effects on Tautomerism of 6-oxo Purine by Polarisable Continuum Method (PCM)

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