2-pyridone as a model nucleophile
DESCRIPTION
2-Pyridone as a Model Nucleophile. 2-Pyridone as a model system for predicting site-specificity of mutagen attack on DNA by Ms. Xiang Wang Master of Science Thesis University of Minnesota Robert M. Carlson Adviser March 1994. Feasibility Study. - PowerPoint PPT PresentationTRANSCRIPT
FEASIBILITY STUDY
2-Pyridone as a model system for predicting site-specificity of mutagen attack on DNA
by Ms. Xiang WangMaster of Science ThesisUniversity of MinnesotaRobert M. Carlson AdviserMarch 1994
- HPLC/MS and GC/MS identification of adducts
- Sodium salt of 2-pyridone mixed 1:1 molar ratios
- Acetonitrile media at room temperature
- Measure adduct formation over time (<24 hours)
Electrophile N-Alkylated (10-4)
O-Alkylated (10-4)
O/N Ratio
I odomethane 32.8 ND OIodothane 24.4 3.16 0.132-idopropane 1.33 3.75 2.83Dimethyl sulfate 24.6 4.32 0.17Diethyl sulfate 22.7 9.79 0.43Nitroso methylurea
2.16 17.9 8.3
Nitroso methylurethane
21,0 19.4 0.92
Trimethylphosphite
ND ND ---
Dimethylphosphite
ND ND ---
Trimethylphosphate
ND ND ---
Styrene oxide ND ND ---
Electrophile N-Alkylated (10-4)
O-Alkylated (10-4)
O/N Ratio
Allyl iodide 33.1 3.19 0.097Allyl bromide 26.3 2.46 0.093Allyl chloride 17.3 ND 01,3-dichloro-1-propene
22.8 1.32 0.058
3-chloro-1-butene
0.41 ND 0
3-chlorocyclohexene
0.683 1.03 1.50
benzylchloride 22.3 1.46 0.066Crotyl chloride 1.8 1.51 0.13
Electrophile N-Alkylation(10-4)
O/N Ratio S. Typhimurium mutangenicity
Methyl nitrosourea 2.16 8.32 841Ethyl nitrosourea 3.51 6.11 202Ethylmethylane sulfate
15.6 0.18 1.70
Diethylsufate 22.7 0.43 24.4Dimethyl sulfate 24.6 0.17 5.8Methyl methane sulfonate
33.7 0.036 0.8