Geometry and Cooperativity Effects in Adenosine−Carboxylic Acid Complexes

Schlund, Sebastian; Mladenović, Milena; Janke, Eline M. Basílio; Engels, Bernd; Weisz, Klaus

doi:10.1021/ja0531430

Cited by 35 publications

(31 citation statements)

References 69 publications

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“…An investigation of some hydrogen-bonded complexes of 1-and 7-15 N-labeled adenine nucleosides and carboxylic acids was performed in a freon solvent [346]. Lowtemperature measurements on adenosine -chloroacetic acid mixtures in an aprotic solvent indicated various co-existing higher-order hydrogen-bonded complexes.…”

Section: Hydrogen Bonding and Prototropic Tautomerismmentioning

confidence: 99%

“…Using density functional theory, Czernek [347] has systematically explored changes in the 15 N and 1 H NMR chemical shielding tensors of the imino group in Watson-Crick nucleic acid base pairs upon hydrogen bonding. Hydrogen-bond donor and acceptor sites at the Watson-Crick (left) and Hoogsteen (right) faces of an adenine nucleobase [346]. He further discusses some possible implications for NMR studies of the dynamics of the 15 N-1 H bond vector and for transverse relaxation-optimized spectroscopy experiments on imino protons.…”

Section: Hydrogen Bonding and Prototropic Tautomerismmentioning

confidence: 99%

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15N NMR Spectroscopy in Structural Analysis: An Update (2001 - 2005)

Marek¹,

Lyčka²,

Kolehmainen³

et al. 2007

COC

131

110

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Since our previous review article (Curr. Org. Chem. 2002, 6, 35), significant improvements and an array of 15 N NMR applications in structural analysis have been published. This report aims to update coverage of improvements in methodology and various types of applications published over the period 2001 -2005. Substantial progress in cryogenic probe technology and the commercial availability of cryoprobes have facilitated the measurement of 15 N NMR parameters.The number of solid-state applications has increased significantly during the past few years. In contrast to our previous review, this article covers 15 N solid-state studies. The 15 N NMR chemical shifts of organic molecules are routinely measured by using cross-polarization magic-angle spinning (CP/MAS) techniques. The principal values of the chemical shift tensors can also be determined. 1 H-15 N and 2 H-15 N distance measurements made by means of 1 H detection are currently used in NMR crystallography.User friendly quantum chemical programs allow for the routine calculation of 15 N chemical shielding and indirect spinspin coupling constants, especially using density functional theory (DFT).Applications of 15 N NMR spectroscopy in various fields of chemistry are summarized here. Major sections represent tautomerism, complexation, protonation, and hydrogen bonding. The other topics comprise N-alkylation, N-oxidation, regioisomerism, and changes in configuration or conformation.

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Section: Hydrogen Bonding and Prototropic Tautomerismmentioning

confidence: 99%

Section: Hydrogen Bonding and Prototropic Tautomerismmentioning

confidence: 99%

15N NMR Spectroscopy in Structural Analysis: An Update (2001 - 2005)

Marek¹,

Lyčka²,

Kolehmainen³

et al. 2007

COC

131

110

View full text Add to dashboard Cite

show abstract

“…Hydrogen bonds are indicated with dotted lines.hydrogen bonds using the Watson-Crick sites[33] N(1) and N(6), hydrogen bonding motif[34] being R 2 2 ð8Þ. These dimers are further organized in hydrogen bonding network via N(6)-HB.…”

mentioning

confidence: 99%

X-ray structures of five variably tert-butoxycarbonyl-substituted adenines and their liquid and solid state NMR investigations

Ikonen

Valkonen

Kolehmainen

2009

Journal of Molecular Structure

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“…All QM/MM calculations were performed with the ChemShell program91 for the MM and the TURBOMOLE program suite 92. Density functional theory is well known to describe many properties with an excellent cost‐benefit ratio,93 but in other cases fails to provide the right answers 94. However, B3‐LYP95 seems to be sufficiently accurate to determine trends in electron densities 84…”

Section: Chapter 2: Comparability Of Electron Densities In Molecular mentioning

confidence: 99%

Can Experimental Electron‐Density Studies be Used as a Tool to Predict Biologically Relevant Properties of Low‐Molecular Weight Enzyme Ligands?

Grabowsky¹,

Jayatilaka²,

Fink³

et al. 2013

Zeitschrift anorg allge chemie

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The case of protease inhibitor model compounds incorporating an aziridine or epoxide ring is used to exemplify how application of experimental electron-density techniques can be used to explain the biological properties of low-molecular weight enzyme ligands. This is * Dr. S. Grabowsky 1905 furthermore seen in the light of a comparison of crystal and enzyme environments employing QM/MM computations to elucidate to which extent the properties in the crystal can be used to predict behavior in the biological surrounding. bidden 222 reflection in diamond. [9] Further major contributions to the development of the multipole model (incomplete list) were made by Kurki-Suonio, [10] Stewart, [11] Hirshfeld, [12] and Coppens. [13] The model developed by Hansen and Coppens in 1978 [1] has proven to be most flexible and is implemented in the most frequently used program packages for experimental electron-density investigations (XD, [14] Mo-Pro, [15] Jana [16] ). The Hansen-Coppens formula for an aspherical pseudoatom used in the refinement is ρ c (r Ǟ ) and ρ v (κ,r Ǟ ) represent the spherical core and spherical valence electron densities, respectively, which are derived from Hartree-Fock wavefunctions expanded over Slater-type basis functions, [17] and are contractible and expansible by the κ parameter. The last term of the sum describes the aspherical deformation of the valence electron density. It consists of a linear combination of real spherical harmonics Y lmϮ with radial functions R l taken as single-zeta orbitals with fixed energy-optimized Slater exponents, [18] contractible and expansible by the κЈ parameter. The populations P v and P lmϮ as well as κ and κЈ are the refinable electron-density parameters. In recent developments, these valence parameters have been transferred to a description of core polarization, i.e. they have been used in an additional refinement of the core electron densities to improve the final density model. [19] Koritsanszky et al. are currently working on an upgraded multipole formalism employing a stockholder-partitioned quantum-mechanical molecular density projected onto nucleus-centered spherical harmonics yielding so-called bonded-atom radial functions analogous to the R l term. [20] X-ray Wavefunction RefinementIn this technique developed by Jayatilaka during the last 15 years, structure and electron-density refinement comparable to

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Geometry and Cooperativity Effects in Adenosine−Carboxylic Acid Complexes

Cited by 35 publications

References 69 publications

15N NMR Spectroscopy in Structural Analysis: An Update (2001 - 2005)

15N NMR Spectroscopy in Structural Analysis: An Update (2001 - 2005)

X-ray structures of five variably tert-butoxycarbonyl-substituted adenines and their liquid and solid state NMR investigations

Can Experimental Electron‐Density Studies be Used as a Tool to Predict Biologically Relevant Properties of Low‐Molecular Weight Enzyme Ligands?

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