反应详情

N-(4-pentenoyl)valyl-pdCpA was prepared. Treatment of S-valine methyl ester with 4-pentenoic anhydride afforded the respective amide as a colorless oil in 73% yield. Following hydrolysis of the ester moiety (LiOH, aq THF), the derived intermediate was converted to the respective cyanomethyl ester (4). Admixture of 4 and pdCpA Robertson, et al., Nucleic Acids Res. 17:9649 (1989), in freshly distilled DMF afforded N-(4-pentenoyl)valyl-pdCpA (5) as a colorless solid in 94% yield. A sample of N-(2-nitroveratryloxycarbonyl)valyl-pdCpA was prepared as described, Robertson, et al., J. Am. Chem. Soc. 113:2722 (1991) for comparative purposes.