Ponomar'ova A H, Iurenko Ie P, Zhurakivs'kyĭ R O, Hovorun D M
Ukr Biokhim Zh (1999). 2011 Mar-Apr;83(2):74-84.
Comprehensive conformational analysis of the biologically active nucleoside 2',3'-didehydro-2',3'-dideoxyadenosine (d4A) has been performed at the MP2/6-311++G(d,p)//DFT B3LYP/6-31G(d,p) level of theory. The energetic, geometrical and polar characteristics of twenty one d4A conformers as well as their conformational equilibrium were investigated. The electron density topological analysis allowed us to establish that the d4A molecule is stabilized by eight types of intramolecular interactions: O5'H...N3, O5'H...C8, C8H...O5', C2'H...N3, C5'H1...N3, C5'H2...N3 Ta C8H...H1/2C5'. The obtained results of conformational analysis lead us to think that d4A may be a terminator of the DNA chain sythesis in the 5'-3' direction. Thus it can be inferred that d4A competes with canonical 2'-deoxyadenosine in binding an active site of the corresponding enzyme.
在MP2/6-311++G(d,p)//DFT B3LYP/6-31G(d,p)理论水平上对生物活性核苷2',3'-二脱氢-2',3'-二脱氧腺苷（d4A）进行了全面的构象分析。研究了21种d4A构象异构体的能量、几何和极性特征及其构象平衡。电子密度拓扑分析使我们能够确定，d4A分子通过八种类型的分子内相互作用得以稳定：O5'H...N3、O5'H...C8、C8H...O5'、C2'H...N3、C5'H1...N3、C5'H2...N3以及C8H...H1/2C5'。构象分析的所得结果使我们认为，d4A可能是5'-3'方向上DNA链合成的终止剂。因此可以推断，d4A在结合相应酶的活性位点时会与标准的2'-脱氧腺苷竞争。
