36197-06-5Relevant academic research and scientific papers
Quinone methide phosphodiester alkylations under aqueous conditions
Zhou,Turnbull
, p. 7072 - 7077 (2001)
A detailed analysis of the alkylation of phosphodiesters with a p-quinone methide under aqueous conditions has been accomplished. The relative rates of phosphodiester alkylation and hydrolysis have been examined by 1H NMR analysis of the reacti
Hydrolysis of the quinone methide of butylated hydroxytoluene in aqueous solutions
Willcockson, Maren Gulsrud,Toteva, Maria M.,Stella, Valentino J.
, p. 3579 - 3585 (2013)
Butylated hydroxytoluene or BHT is an antioxidant commonly used in pharmaceutical formulations. BHT upon oxidation forms a quinone methide (QM). QM is a highly reactive electrophilic species that can undergo nucleophilic addition. Here, the kinetic reactivity of QM with water at various apparent pH values in a 50% (v/v) water-acetonitrile solution at constant ionic strength of I =?0.5 (NaCl)4, was studied. The hydrolysis of QM in the presence of added acid, base, sodium chloride, and phosphate buffer resulted in the formation of only one product--the corresponding 3,5-di-tert-butyl-4-hydroxybenzyl alcohol (BA). The rate of BA formation was catalyzed by the addition of acid and base, but not chloride and phosphate species. Nucleophilic excipients, used in the pharmaceutical formulation, or nucleophilic groups on active pharmaceutical ingredient molecule may form adducts with QM, the immediate oxidative product of BHT degradation, thus having implications for drug product impurity profiles. Because of these considerations, BHT should be used with caution in formulations containing drugs or excipients capable of acting as nucleophiles.
Phosphodiester alkylation with a quinone methide
Zhou, Qibing,Turnbull, Kenneth D.
, p. 2847 - 2851 (1999)
Despite the wide array of studies involving DNA alkylation and cleavage with quinone methide generating compounds, there have been no reports on the alkylation of phosphodiesters with quinone methides. We have investigated the reaction of dialkyl phosphat
Biomolecular labeling
-
Sheet 30; 84, (2010/01/31)
A method for using an organic compound to label polynucleotides is described. The method utilizes an organic compound including an oligonucleotide, and electrophilic active site, an active complex, and a phosphate binding site. The oligonucleotide has a sequence that is complimentary to a specific region of a polynucleotide. This facilitates labeling of DNA or RNA at a specific site in its sequence. The active site consists of a stable precursor, and only becomes reactive upon activation. Leaving and protecting functional groups may be attached to the active site in order to facilitate the formation of a stable precursor and subsequent activation. The active complex may be a drug, polypeptide or a reporter molecule such as an isotope or fluorescing compound. The phosphate binding sites may be any functional group capable of forming ionic bonds with phosphate oxygens. Nucleotide labeling using this compound does not interfere with a polynucleotide sequence. The described method for utilizing this compound may be performed in situ. Latent reactivity is utilized to make the reaction chemically specific, alkylating only phosphodiester groups on the polynucleotide. A lactonization reaction traps the trialkylphosphate in a stable form.
Oxidation by Cobalt(III) Acetate. Part 13. Oxidation of Substituted Phenols with Cobalt(III) Acetate in Acetic Acid
Hirano, Masao,Ishii, Tadamichi,Morimoto, Takashi
, p. 1434 - 1436 (2007/10/02)
The oxidation of 2,6-di- and 2,4,6-tri-substituted phenols with cobalt(III) acetate has been investigated in acetic acid under an inert atmosphere; the former gave the corresponding diphenoquinones in excellent yields, and the latter yielded side-chain or nuclear acetoxylated products in moderate to good yields.
