Biomaterial Database

Alkylation of guanosine and 2'-deoxyguanosine by o-quinone alpha-(p-anisyl)methide in aqueous solution. 2004

Yvonne Chiang, and A Jerry Kresge

Department of Chemistry, University of Toronto, Toronto, Ontario M5S 3H6, Canada.

Rates of alkylation of guanosine and 2'-deoxyguanosine with o-quinone alpha-(p-anisyl)methide were measured by flash photolysis in a series of aqueous sodium hydroxide solutions and bicarbonate ion, t-butylhydrogenphosphonate ion, and biphosphate ion buffers. The data so obtained provide rate profiles for these nucleoside plus quinone methide reactions over the range pH = 7-14, which furnish guanosine and deoxyguanosine acidity constants consistent with literature information. These profiles also provide rate constants that show the reaction of o-quinone alpha-(p-anisyl)methide with guanosine and deoxyguanosine to be fairly fast processes, considerably faster than the biologically wasteful reaction of the quinone methide with water, which is the ubiquitous medium in biological systems; that makes the quinone methide a potent guonosine and deoxyguanosine alkylator.

UI	MeSH Term	Description	Entries
D007700	Kinetics	The rate dynamics in chemical or physical systems.
D011809	Quinones	Hydrocarbon rings which contain two ketone moieties in any position. They can be substituted in any position except at the ketone groups.
D003849	Deoxyguanosine	A nucleoside consisting of the base guanine and the sugar deoxyribose.
D006151	Guanosine	A purine nucleoside that has guanine linked by its N9 nitrogen to the C1 carbon of ribose. It is a component of ribonucleic acid and its nucleotides play important roles in metabolism. (From Dorland, 28th ed)
D000478	Alkylation	The covalent bonding of an alkyl group to an organic compound. It can occur by a simple addition reaction or by substitution of another functional group.	Alkylations
D014867	Water	A clear, odorless, tasteless liquid that is essential for most animal and plant life and is an excellent solvent for many substances. The chemical formula is hydrogen oxide (H2O). (McGraw-Hill Dictionary of Scientific and Technical Terms, 4th ed)	Hydrogen Oxide
D015394	Molecular Structure	The location of the atoms, groups or ions relative to one another in a molecule, as well as the number, type and location of covalent bonds.	Structure, Molecular,Molecular Structures,Structures, Molecular