BIOMAT Database Logo BIOMAT Database Logo

Synthesis of the fully protected phosphoramidite of the benzene-DNA adduct, N2-(4-Hydroxyphenyl)-2'-deoxyguanosine and incorporation of the later into DNA oligomers. 2008

Ahmed Chenna, and Ramesh C Gupta, and Radha R Bonala, and Francis Johnson, and Bo Hang
Monogram Biosciences Inc, South San Francisco, California, USA.

N(2)- (4-Hydroxyphenyl)-2'-deoxyguanosine-5'-O-DMT-3'-phosphoramidite has been synthesized and used to incorporate the N(2)-(4-hydroxyphenyl)-2'-dG (N(2)-4-HOPh-dG) into DNA, using solid-state synthesis technology. The key step to obtaining the xenonucleoside is a palladium (Xantphos-chelated) catalyzed N(2)-arylation (Buchwald-Hartwig reaction) of a fully protected 2'-deoxyguanosine derivative by 4-isobutyryloxybromobenzene. The reaction proceeded in good yield and the adduct was converted to the required 5'-O-DMT-3'-O-phosphoramidite by standard methods. The latter was used to synthesize oligodeoxynucleotides in which the N(2)-4-HOPh-dG adduct was incorporated site-specifically. The oligomers were purified by reverse-phase HPLC. Enzymatic hydrolysis and HPLC analysis confirmed the presence of this adduct in the oligomers.

UI MeSH Term Description Entries
D008956 Models, Chemical Theoretical representations that simulate the behavior or activity of chemical processes or phenomena; includes the use of mathematical equations, computers, and other electronic equipment. Chemical Models,Chemical Model,Model, Chemical
D009838 Oligodeoxyribonucleotides A group of deoxyribonucleotides (up to 12) in which the phosphate residues of each deoxyribonucleotide act as bridges in forming diester linkages between the deoxyribose moieties. Oligodeoxynucleotide,Oligodeoxyribonucleotide,Oligodeoxynucleotides
D009943 Organophosphorus Compounds Organic compounds that contain phosphorus as an integral part of the molecule. Included under this heading is broad array of synthetic compounds that are used as PESTICIDES and DRUGS. Organophosphorus Compound,Organopyrophosphorus Compound,Organopyrophosphorus Compounds,Compound, Organophosphorus,Compound, Organopyrophosphorus,Compounds, Organophosphorus,Compounds, Organopyrophosphorus
D010165 Palladium A chemical element having an atomic weight of 106.4, atomic number of 46, and the symbol Pd. It is a white, ductile metal resembling platinum, and following it in abundance and importance of applications. It is used in dentistry in the form of gold, silver, and copper alloys.
D002384 Catalysis The facilitation of a chemical reaction by material (catalyst) that is not consumed by the reaction. Catalyses
D002851 Chromatography, High Pressure Liquid Liquid chromatographic techniques which feature high inlet pressures, high sensitivity, and high speed. Chromatography, High Performance Liquid,Chromatography, High Speed Liquid,Chromatography, Liquid, High Pressure,HPLC,High Performance Liquid Chromatography,High-Performance Liquid Chromatography,UPLC,Ultra Performance Liquid Chromatography,Chromatography, High-Performance Liquid,High-Performance Liquid Chromatographies,Liquid Chromatography, High-Performance
D001554 Benzene Toxic, volatile, flammable liquid hydrocarbon byproduct of coal distillation. It is used as an industrial solvent in paints, varnishes, lacquer thinners, gasoline, etc. Benzene causes central nervous system damage acutely and bone marrow damage chronically and is carcinogenic. It was formerly used as parasiticide. Benzol,Benzole,Cyclohexatriene
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
D018736 DNA Adducts The products of chemical reactions that result in the addition of extraneous chemical groups to DNA. DNA Adduct,Adduct, DNA,Adducts, DNA

Related Publications

Ahmed Chenna, and Ramesh C Gupta, and Radha R Bonala, and Francis Johnson, and Bo Hang
Benzene-derived N2-(4-hydroxyphenyl)-deoxyguanosine adduct: UvrABC incision and its conformation in DNA.
March 2010, Toxicology letters,
Ahmed Chenna, and Ramesh C Gupta, and Radha R Bonala, and Francis Johnson, and Bo Hang
Synthesis of a benzene metabolite adduct, 3"-hydroxy-1,N2-benzetheno-2'-deoxyguanosine, and its site-specific incorporation into DNA oligonucleotides.
February 1997, Chemical research in toxicology,
Ahmed Chenna, and Ramesh C Gupta, and Radha R Bonala, and Francis Johnson, and Bo Hang
Synthesis of the PhIP adduct of 2'-deoxyguanosine and its incorporation into oligomeric DNA.
June 2006, Chemical research in toxicology,
Ahmed Chenna, and Ramesh C Gupta, and Radha R Bonala, and Francis Johnson, and Bo Hang
Synthesis of N2-(4-hydroxyphenyl)-2'-deoxyguanosine 3'-phosphate: comparison by 32P-postlabeling with the DNA adduct formed in HL-60 cells treated with hydroquinone.
January 1996, Chemical research in toxicology,
Ahmed Chenna, and Ramesh C Gupta, and Radha R Bonala, and Francis Johnson, and Bo Hang
Synthesis of 2'-N-methylamino-2'-deoxyguanosine and 2'-N,N-dimethylamino-2'-deoxyguanosine and their incorporation into RNA by phosphoramidite chemistry.
November 2011, The Journal of organic chemistry,
Ahmed Chenna, and Ramesh C Gupta, and Radha R Bonala, and Francis Johnson, and Bo Hang
Synthesis of 2'-deoxyoxanosine from 2'-deoxyguanosine, conversion to its phosphoramidite, and incorporation into oxanine-containing oligodeoxynucleotides.
June 2010, Current protocols in nucleic acid chemistry,
Ahmed Chenna, and Ramesh C Gupta, and Radha R Bonala, and Francis Johnson, and Bo Hang
Incorporation of N2-deoxyguanosine metabolic adducts of 2-aminonaphthalene and 2-aminofluorene into oligomeric DNA.
March 2005, Chemical research in toxicology,
Ahmed Chenna, and Ramesh C Gupta, and Radha R Bonala, and Francis Johnson, and Bo Hang
Predominance of the 1,N2-propano 2'-deoxyguanosine adduct among 4-hydroxy-2-nonenal-induced DNA lesions.
July 2004, Free radical biology & medicine,
Ahmed Chenna, and Ramesh C Gupta, and Radha R Bonala, and Francis Johnson, and Bo Hang
Synthesis of a 4-selenothymidine phosphoramidite and incorporation into oligonucleotides.
March 2008, Current protocols in nucleic acid chemistry,
Ahmed Chenna, and Ramesh C Gupta, and Radha R Bonala, and Francis Johnson, and Bo Hang
Synthesis of 1,N2-(1,3-propano)-2'-deoxyguanosine and incorporation into oligodeoxynucleotides: a model for exocyclic acrolein-DNA adducts.
January 1990, Chemical research in toxicology,
Copied contents to your clipboard!