Author:
Cadet Jean,Voituriez Lucienne,Hruska Frank E.,Kan Lou-Sing,Leeuw Frank A. A. M. de,Altona Cornelis
Abstract
We describe the preparation of the six configurationally distinct cyclobutane-type photodimers generated by the acetone-sensitized uv irradiation of thymidine in aqueous solution. Also prepared as minor photoproducts are the 5R and 5S di-astereoisomers of 5,6-dihydrothymidine, and two novel molecules, the 5R and 5S diastereoisomers of 5-acetonyl-5,6-dihydrothymidine. The purification of the ten molecules by chromatographic techniques (hplc, tlc) is described, along with their extensive characterization by uv, ir, cd, FAB-ms and 1H nmr. The proton chemical shifts and coupling constants are discussed in terms of the geometry of the pyrimidine, cyclobutane, and sugar rings.
Publisher
Canadian Science Publishing
Subject
Organic Chemistry,General Chemistry,Catalysis
Cited by
62 articles.
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