环氧三氯丙烷、环氧氯丙烷和缩水甘油的7-烷基脱氧鸟苷的稳定性。

Stability of 7-alkyldeoxyguanosines of trichloropropylene oxide, epichlorohydrin and glycidol.

作者信息

Hemminki K, Lax M

出版信息

Acta Pharmacol Toxicol (Copenh). 1986 Jul;59(1):80-5. doi: 10.1111/j.1600-0773.1986.tb00137.x.

DOI:10.1111/j.1600-0773.1986.tb00137.x

Abstract

Deoxyguanosine was reacted with trichloropropylene oxide (TCPO), epichlorohydrin and glycidol in aqueous solution and the products were isolated by high pressure liquid chromatography (HPLC). For each compound 7-alkyldeoxyguanosine was the main adduct; TPCO reacted about 3 times faster than epichlorohydrin and about 10 times faster than glycidol. The pKa's of the 7-alkyldeoxyguanosines were 6.7, 6.8 and 6.9 for the TCPO-, epichlorohydrin-, and glycidol-adducts, respectively. The respective half-lives of imidazole ring-opening were 6.3, 15 and 27 hrs (pH 8.5, 28 degrees) and those of depurination 1.9, 3.4 and 4.4 hrs (pH 5.5, 28 degrees).

摘要

脱氧鸟苷在水溶液中与三氯环氧丙烷（TCPO）、环氧氯丙烷和缩水甘油反应，产物通过高压液相色谱（HPLC）分离。对于每种化合物，7-烷基脱氧鸟苷是主要加合物；TCPO的反应速度比环氧氯丙烷快约3倍，比缩水甘油快约10倍。TCPO加合物、环氧氯丙烷加合物和缩水甘油加合物的7-烷基脱氧鸟苷的pKa分别为6.7、6.8和6.9。咪唑环开环的各自半衰期分别为6.3、15和27小时（pH 8.5，28℃），脱嘌呤的半衰期分别为1.9、3.4和4.4小时（pH 5.5，28℃）。