The (α-4) photoconjugates of 5-methylcytosine, 1,5-dimethylcytosine, 1-methylthymine and thymidine.

Abstract:

:The pyrimidine nucleobases contained in DNA undergo a variety of photoinduced reactions in which two moieties become joined to form a product (e.g. formation of cyclobutane dimers and [6-4] adducts). Herein, we describe a new type of photoconjugation reaction that has been shown to occur for 5-methylcytosine (5-MeC), 1,5-dimethylcytosine (1,5-diMeC), 1-methylthymine and thymidine; in this reaction the 5-methyl group of one nucleobase (or nucleoside) becomes attached to the 4-position of the second moiety. For example, 5-MeC forms α-4'-(5'-methylpyrimidin-2'-one)-5-methylcytosine. The various (α-4) conjugates are produced upon irradiation of the parent compound in frozen aqueous solution at -78.5°C. The UV spectra of these compounds display a characteristic "double humped" profile, similar to that expected from overlaying the spectrum of parent nucleobase with that of a 2'-pyrimidone moiety. Preliminary results suggest that thymine and 5-methyl-2'-deoxycytidine (5-MedCyd) form analogous photoproducts. A variety of other previously unreported photoproducts are described as well for the 5-MeC, 1,5-diMeC and 5-MedCyd systems.

journal_name

Photochem Photobiol

authors

Shetlar MD,Chung J

doi

10.1111/j.1751-1097.2011.01070.x

subject

Has Abstract

pub_date

2012-03-01 00:00:00

pages

336-43

issue

2

eissn

0031-8655

issn

1751-1097

journal_volume

88

pub_type

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