Accelerated hydrolysis of α-halo and α-cyano pyridinium relative to uracil derivatives: a model for ODCase-catalyzed hydrolysis of 6-cyanoUMP
Author:
Publisher
Elsevier BV
Subject
Organic Chemistry,Drug Discovery,Biochemistry
Reference24 articles.
1. Surprisingly Low Aqueous Acidity at the α-Positions of Pyridiniums and Pyrimidinium: The Role of Solvation
2. Equilibrium of Formation of the 6-Carbanion of UMP, a Potential Intermediate in the Action of OMP Decarboxylase
3. Stability of the 6-Carbanion of Uracil Analogues: Mechanistic Implications for Model Reactions of Orotidine-5‘-monophosphate Decarboxylase
4. Carbanions from decarboxylation of orotate analogs: Stability and mechanistic implications
5. Formation and Stability of a Vinyl Carbanion at the Active Site of Orotidine 5‘-Monophosphate Decarboxylase: pKa of the C-6 Proton of Enzyme-Bound UMP
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1. 15.1.4 Pyridines (Update 2016);Knowledge Updates 2016/1;2016
2. Nucleophilic Aromatic Substitution;Organic Reaction Mechanisms Series;2014-04-04
3. Reactivity in the nucleophilic aromatic substitution reactions of pyridinium ions;Org. Biomol. Chem.;2014
4. Stabilities of uracil and pyridone-based carbanions: a systematic study in the gas phase and solution and implications for the mechanism of orotidine-5′-monophosphate decarboxylase;Tetrahedron;2013-07
5. The Element Effect Revisited: Factors Determining Leaving Group Ability in Activated Nucleophilic Aromatic Substitution Reactions;The Journal of Organic Chemistry;2012-10-17
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