Different Activities of 5-Hydroxy-dUMP and 5-Hydroxymethyl-dUMP in Thymidylate Synthase-Catalyzed Reaction in View of Molecular Modeling and Structural Studies

Jarmuła, Adam; Leś, Andrzej; Rode, Wojciech

doi:10.1006/bioo.2000.1172

Cited by 3 publications

(1 citation statement)

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“…Our experience based on over 15 years using the model [30][31][32] suggests that considering too many canonical structures leads to inefficient differentiation between the weights. [37][38][39] In spite of the approximations of the model, it was recently successfully applied by Bird 40 for the estimation of resonance energies of azines and azoles. It was shown that in the case of benzenoid hydrocarbons the HOSE calculated weights are closely equivalent to those of Randić.…”

Section: Equationmentioning

confidence: 99%

Angular Group Induced BondAlternation (AGIBA). A New Face of Substituent Effect Detectedin Molecular Geometry

Krygowski¹,

Cyrański²

2003

Synlett

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Angular Group Induced Bond Alternation is a new face of a substituent effect well documented by careful analysis of molecular geometry. The angular groups attached to monocyclic 6-πelectron systems cause substantial changes to π-electron distribution in the ring. Different patterns are found for X-Y and X=Y types of groups. The overall effect is due to the rehybridization effect, the through space π-electron interactions between a group and the ring, possibly also by other subtle effects, eg. the negative hyperconjugation. The effect is strongly conformational dependent. While the AGIBA is energetically weak, it is structurally strong enough that other interactions in monocyclic systems, eg. through -resonance type interactions do not reduce it. In polycyclic benzenoid hydrocarbons AGIBA works only locally while in non-cyclic π-electron systems the effect does not work at all.

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