Cinnamoylation of the sugar hydroxyls of 3-methylthymidine. Formation of a relatively stable ester derivative.
A trace amount (51 ng) of 3-methylthymidine is derivatized with cinnamic anhydride in the presence of the acylation catalyst 4-dimethylaminopyridine. The yield of the diacylated product, 3'-5'-bis-(O-cinnamoyl)-3-methylthymidine, is 102 +/- 3.6%. The product is stable at pH 4-8 in aqueous acetonitrile for 16 days and can be determined at the low pg level by gas chromatography with electron-capture detection. These results encourage the further development of alpha,beta-unsaturated acylating reagents for use in this and related chromatographic analyses.
D055598:Chemical Phenomena; D002621:Chemistry; D002849:Chromatography, Gas; D002851:Chromatography, High Pressure Liquid; D002934:Cinnamates / Q000032:analysis / Q000138:chemical synthesis; D004355:Drug Stability; D006900:Hydroxylation; D007202:Indicators and Reagents; D013936:Thymidine / Q000031:analogs & derivatives* / Q000032:analysis
D002934:Cinnamates; D007202:Indicators and Reagents; C012439:methylthymidine; D013936:Thymidine