Photochemistry of 5-fluorouracil dideoxyribonucleoside monophosphate.
5-Fluorouracil is an artificial nucleobase analog of thymine and uracil, with a substituent in the 5-position that has a mass similar to the methyl group in thymine, but very different electronic, steric and vibrational coupling properties. UVC irradiation of 5-fluorouracil dideoxyribonucleoside monophosphate (dXpdX) is examined here with mass spectrometry and UV-Vis absorption spectroscopy and is compared to the UV photochemistry of other pyrimidine dideoxyribonucleoside monophosphates. The results show that the photochemical products and kinetics of dXpdX are similar to those of uracil dideoxyribonucleoside monophosphate and similar to those of the isolated 5-fluorouracil nucleobase. The photochemistry of dXpdX is compared to the photochemistry of thymine and uracil dideoxyribonucleoside monophosphates.
Faichuk
Melissa
M
Department of Chemistry, University of Alberta, Edmonton, AB, Canada.
Mah
Allison
A
Loppnow
Glen R
GR
D003854:Deoxyribonucleotides / Q000737:chemistry*; D015224:Dideoxynucleosides / Q000737:chemistry*; D005472:Fluorouracil / Q000031:analogs & derivatives* / Q000737:chemistry; D013058:Mass Spectrometry; D015394:Molecular Structure; D010777:Photochemistry; D013053:Spectrophotometry
C526326:5-fluorouracil dideoxyribonucleoside monophosphate; D003854:Deoxyribonucleotides; D015224:Dideoxynucleosides; D005472:Fluorouracil