Stereochemistry of reaction products of 1,3-dimethylthymine epoxide with amines

✍ Scribed by Takashi Harayama; Reiko Yanada; Tooru Taga; Fumio Yoneda

• Book ID: 104222389
• Publisher: Elsevier Science
• Year: 1985
• Tongue: French
• Weight: 221 KB
• Volume: 26
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)89197-2

✦ Synopsis

Reaction of 1,3_dimethylthymine epoxide with amines afforded cis and trans adducts, stereostructures of which were elucidated and treatment of trans adduct with boron trifluoride etherate afforded cis adduct; mechanism for the isomerization is presented. Much attention has focused on the oxidations of nucleic acids and their components with active oxygens and on the formation of nucleic acid-protein cross-linkages in relation to the study of mutagenesis and carcinogenesis. 192 Recently, we reported the oxidation of some pyrimidine bases with m-chloroperbenzoic acid as a representative of acylperoxide. 3,4 In this oxidation we supposed the epoxide Q5 as the reaction intermediate which was subjected to nucleophiles to afford products. 4 Then, we have envisaged the reaction of (l_) with amine or amino acid as a