Bransome E D, Hendry L B, Muldoon T G, Mahesh V B, Hutson M S, Campbell L K
J Theor Biol. 1985 Jan 7;112(1):97-108. doi: 10.1016/s0022-5193(85)80118-1.
The shape of the space occupied by a model of the estrogenic steroid hormone estradiol-17 beta conforms closely to a helical cavity between neighboring base pairs in partially coiled B-DNA. The orientation of estradiol-17 beta when fitted into DNA allows stereochemically complementary hydrogen bonding of both the 3- and 17 beta-hydroxyl groups to phosphate oxygens of the deoxyribose-phosphate backbone on adjacent strands. Changes in the chirality (handedness) of the steroid skeleton or in the absolute stereochemistry of hydrogen bonding groups prevent formation of complementary fits in the DNA. Synthetic estrogens can also adopt conformations which are stereochemically complementary to the cavities between base pairs. The complementary relationships between active estrogens and nucleic acids may be related to constraints on the evolution of the structure and the biological function of steroids.
雌激素类固醇激素β-雌二醇模型所占据的空间形状与部分卷曲的B-DNA中相邻碱基对之间的螺旋腔紧密契合。当β-雌二醇嵌入DNA时，其取向使得3-羟基和17β-羟基都能与相邻链上脱氧核糖-磷酸主链的磷酸氧形成立体化学互补的氢键。类固醇骨架手性（旋向性）的改变或氢键基团绝对立体化学的改变会阻止在DNA中形成互补契合。合成雌激素也能采取与碱基对之间的腔立体化学互补的构象。活性雌激素与核酸之间的互补关系可能与对类固醇结构和生物学功能进化的限制有关。
