The non-bonded interactions in D-glucose and β-maltose: an ab initio study of conformations produced by empirical force-field calculations

Melberg, Steen; Rasmussen, Kjeld; Scordamaglia, R.; Tosi, Camillo

doi:10.1016/0008-6215(79)80003-8

Cited by 36 publications

(13 citation statements)

References 12 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…However, because of the hydrogen-bond energy advantage noted above, when the total harmonic Table 3. B3LYP/6-311++G ÃÃ electronic energy, harmonic zero point vibrational energy (ZPVE), enthalpy (H), entropy (S), free energy (G), and numerical Hessian (NUMH) results for a-and b-D D -glucopyranose 4 Gibbs free energy ðG o 298 ¼ E elec þ ðH À TSÞ þ RT Þ is calculated, the a-anomer gg conformation remains $0.3 kcal/mol lower in free energy than the lowest energy gg conformer of the b-anomer. Of interest is the observation in Table 1 that after the NUMHESS frequency results are included, the a-anomer gg and gt free energies remain slightly lower than the b-anomer conformers, and are $0.4-0.7 kcal/mol lower in energy than the a-and b-anomer tg conformers, respectively.…”

Section: C 1 Chair Conformationsmentioning

confidence: 99%

“…Melberg et al, 4 Polavarapu and Ewig, 5 and Jebber et al 16 carried out ab initio studies using small basis sets (e.g., 3-21G, 16 and 4-31G 4 ) at the Hartree Fock level with some energies calculated at the 6-31G Ã level 5;16 on several conformations of glucose. From the 4-31G calculations, 5 the a-anomer energy was lower than the b-anomer by $2 kcal/mol, and upon calculation of the free energy at the 6-31G Ã level, the a-anomer remained $0.4 kcal/mol lower in energy.…”

Section: Introductionmentioning

confidence: 99%

“…There is considerable ab initio and density functional literature on a-and b-D D -glucopyranose [4][5][6][7][8][9][10][11][12][13][14][15][16][17] . Many of these studies are calculations in which small basis sets were applied to carbohydrates (i.e., semi-empirical, HF/ 4-31G, HF/6-31G Ã ), 4-10;12;16;17 or the geometry results of smaller basis sets have been used to get energies at larger basis sets without further geometry optimization using the larger basis sets 12;14;15 .…”

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

B3LYP/6-311++G** study of α- and β-d-glucopyranose and 1,5-anhydro-d-glucitol: 4C1 and 1C4 chairs, 3,OB and B3,O boats, and skew-boat conformations

Appell

Strati

Willett

et al. 2004

Carbohydrate Research

121

113

View full text Add to dashboard Cite

Section: C 1 Chair Conformationsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

B3LYP/6-311++G** study of α- and β-d-glucopyranose and 1,5-anhydro-d-glucitol: 4C1 and 1C4 chairs, 3,OB and B3,O boats, and skew-boat conformations

Appell

Strati

Willett

et al. 2004

Carbohydrate Research

121

113

View full text Add to dashboard Cite

“…4 hartrees. The energy difference between the two molecules is 0.0 1 1 hartree (6.9 kcal/mol), a-L-sorbopyranose being the more stable.…”

Section: Total Energies and Dipole Momentsmentioning

confidence: 99%

Examination of the molecular properties of D-fructose and L-sorbose by abinitio LCAO-MO calculations

Szarek¹,

Korppi-Tommola²,

Martin³

et al. 1984

Can. J. Chem.

View full text Add to dashboard Cite

Abinitio SCF LCAO-MO calculations at the STO-3G level have been performed on β-D-fructopyranose (1) and α-L-sorbopyranose (2) using crystallographic data as the geometrical input. Molecular properties of 1 and 2 are discussed in terms of orbital energies, total energy, ionization potentials, Mulliken population analysis, and electrostatic potentials, with a particular emphasis on the possible consequences of these features as regards the sweet taste of these two ketoses. No correlation was found, for example, with the electrostatic, point-charge distribution since the calculated hydrogen-bonding abilities would lead to the prediction of 2 being sweeter than 1. On the other hand, non-bonded overlap populations between oxygen and hydroxyl-hydrogen atoms reveal the presence of intramolecular interactions, which may have a determinant influence on the taste of these molecules and which could explain why D-fructose is much sweeter than its epimer at C-5, namely, L-sorbose.

show abstract

“…Tvarõska et al, 11 while investigating the stereochemistry of the two anomers of D-glucopyranose and some disaccharides derivatives in solution have also applied the semiempirical PCILO method. In addition, the ab initio method has been widely employed to compute conformations of isolated molecules of ␣-and ␤-D-glucose, especially in the works using the minimal basis set SCF-MO 12,13 and those using both the 4-31G and 6-31G* basis sets. 14 These kinds of molecules need prolonged computing time for ab initio calculations.…”

Section: Introductionmentioning

confidence: 99%

Structures and energies of D‐galactose and galabiose conformers as calculated by ab initio and semiempirical methods

et al. 2003

View full text Add to dashboard Cite

Optimized geometries and total energies of some conformers of alpha- and beta-D-galactose have been calculated using the RHF/6-31G* ab initio method. Vibrational frequencies were computed at the 6-31G* level for the conformers that favor internal hydrogen bonding, in order to evaluate their enthalpies, entropies, Gibbs free energies, and then their structural stabilities. The semiempirical AM1, PM3, MNDO methods have also been performed on the conformers GG, GT, and TG of alpha- and beta-D-galactose. In order to test the reliability of each semiempirical method, the obtained structures and energies from the AM1, PM3, and MNDO methods have been compared to those achieved using the RHF/6-31G* ab initio method. The MNDO method has not been investigated further, because of the large deviation in the structural parameters compared with those obtained by the ab initio method for the galactose. The semiempirical method that has yielded the best results is AM1, and it has been chosen to perform structural and energy calculations on the galabiose molecule (the disaccharides constituted by two galactose units alpha 1,4 linked). The goal of such calculations is to draw the energy surface maps for this disaccharide. To realize each map, 144 different possible conformations resulting from the rotations of the two torsional angles psi and phi of the glycosidic linkage are considered. In each calculation, at each increment of psi and phi, using a step of 30 degrees from 0 to 330 degrees, the energy optimization is employed. In this article, we report also calculations concerning the galabiose molecule using different ab initio levels such as RHF/6-31G*, RHF/6-31G**, and B3Lyp/6-31G*.

show abstract

The non-bonded interactions in D-glucose and β-maltose: an ab initio study of conformations produced by empirical force-field calculations

Cited by 36 publications

References 12 publications

B3LYP/6-311++G** study of α- and β-d-glucopyranose and 1,5-anhydro-d-glucitol: 4C1 and 1C4 chairs, 3,OB and B3,O boats, and skew-boat conformations

B3LYP/6-311++G** study of α- and β-d-glucopyranose and 1,5-anhydro-d-glucitol: 4C1 and 1C4 chairs, 3,OB and B3,O boats, and skew-boat conformations

Examination of the molecular properties of D-fructose and L-sorbose by abinitio LCAO-MO calculations

Structures and energies of D‐galactose and galabiose conformers as calculated by ab initio and semiempirical methods

Contact Info

Product

Resources

About