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首页> 外文期刊>Chemistry: A European journal >Pentafluorophenyl-Phenyl Interactions in Biphenyl-DNA
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Pentafluorophenyl-Phenyl Interactions in Biphenyl-DNA

机译：联苯DNA中的五氟苯基-苯基相互作用

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摘要

We prepared and investigated oligonucleotide duplexes of the sequence d(GATGAC(X)_nGCTAG)centre dotd(C-TAGC(Y)_nGTCATC),in which X and Y designate biphenyl- (bph) and penta-fluorobiphenyl- (~(5F)bph) C-nucleotides,respectively,and n varies from 0-4.These hydrophobic base substitutes are expected to adopt a zipperlike,inter-strand stacking motif,in which not only bph/bph or ~(5F)bph/~(3F)bph homo pairs,but also ~(5F)bph/bph mixed pairs can be formed.By performing UV-melting curve analysis we found that incorporation of a single ~(5F)bph/~(5F)bph pair leads to a duplex that is essentially as stable as the unmodified duplex (n=0),and 2.4 K more stable than the duplex with the nonfluorinated bph/bph pair.The T_m of the mixed bph/~(5F)bph pair was in between the T_m values of the respective homo pairs.Additional,unnatural aromatic pairs increased the T_m by +3.0-4.4 K/couple,irrespective of the nature of the aromatic residue.A thermody-namic analysis Using isothermal titra-tion calorimetry (ITC) of a series of duplexes with n=3 revealed lower (less negative) duplex formation enthalpies (DELTAH) in the ~(5F)bph/~(5F)bph case than in the bph/bph case,and confirmed the higher thermodynamic stability (DELTAG) of the fluorinated duplex,suggesting it to be of entropic origin.Our data are compatible with a model in which the stacking of ~(5F)bph versus bph is dominated by dehydration of the aromatic units upon duplex formation.They do not support a model in which van der Waals dispersive forces (induced dipoles) or electrostatic (quadrupole) interactions play a dominant role.
机译：我们准备并研究了以d（GATGAC（X）_nGCTAG）中心点缀（C-TAGC（Y）_nGTCATC）序列形成的寡核苷酸双链体，其中X和Y分别表示联苯-（bph）和五氟联苯-（〜（5F） bph）C核苷酸，且n介于0-4之间。这些疏水性碱基替代物有望采用拉链状链间堆积基序，其中不仅bph / bph或〜（5F）bph /〜（3F bph同形对，但也可以形成〜（5F）bph / bph混合对。通过进行UV熔解曲线分析，我们发现掺入单个〜（5F）bph /〜（5F）bph对可导致双链体基本上与未修饰的双链体（n = 0）一样稳定，并且比非氟化bph / bph对的双链体稳定2.4 K.bph /〜（5F）bph混合对的T_m在T_m值之间不依赖于芳族残基的性质，额外的非天然芳族对使T_m增加+ 3.0-4.4 K /对。使用等温滴定热法进行热动力学分析一系列n = 3的双链体（ITC）显示〜（5F）bph /〜（5F）bph情况下的双链形成焓（DELTAH）低于bph / bph情况下的双链形成焓（DELTAH），并证实较高氟化双链体的热力学稳定性（DELTAG），表明它是熵的来源。我们的数据与其中双链形成时芳族单元脱水占主导地位的〜（5F）bph与bph的堆积模型兼容。不支持范德华分散力（感应偶极子）或静电（四极子）相互作用起主导作用的模型。

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