Van den Eeckhout E, De Bruyn A, Pepermans H, Esmans E L, Vryens I, Claereboudt J, Claeys M, Sinsheimer J E
University of Ghent, College of Pharmacy, Belgium.
J Chromatogr. 1990 Mar 30;504(1):113-28. doi: 10.1016/s0021-9673(01)89518-2.
Thymidine and 2'-deoxyadenosine were reacted with phenyl glycidyl ether in order to study the formation of the corresponding 2'-deoxynucleoside adducts. Separation methods were elaborated using either reversed-phase high-performance liquid chromatography with photodiode-array detection, or centrifugal circular thin-layer chromatography. The adducts were isolated on a preparative scale and were fully characterized by UV spectroscopy, desorption chemical ionization and fast atom bombardment mass spectrometry and 270- and 360-MHz 1H NMR spectrometry. For thymidine the main adduct was characterized as N-3-(2-hydroxy-3-phenoxypropyl)thymidine. With 2'-deoxyadenosine, predominantly N-1-(2-hydroxy-3-phenoxypropyl)-2'-deoxyadenosine was formed. With longer reaction times, the formation of a minor amount of dialkylated 2'-deoxyadenosine was observed. These nucleoside adducts will be used as marker compounds for studies of DNA adduct formation.
将胸苷和2'-脱氧腺苷与苯基缩水甘油醚反应，以研究相应的2'-脱氧核苷加合物的形成。采用反相高效液相色谱-光电二极管阵列检测法或离心圆形薄层色谱法精心制定了分离方法。在制备规模上分离出加合物，并通过紫外光谱、解吸化学电离和快原子轰击质谱以及270兆赫和360兆赫的1H核磁共振光谱对其进行了全面表征。对于胸苷，主要加合物被表征为N-3-(2-羟基-3-苯氧基丙基)胸苷。对于2'-脱氧腺苷，主要形成N-1-(2-羟基-3-苯氧基丙基)-2'-脱氧腺苷。反应时间延长时，观察到少量二烷基化2'-脱氧腺苷的形成。这些核苷加合物将用作研究DNA加合物形成的标记化合物。
