Base-boronated dinucleotides: synthesis and effect of N7-cyanoborane substitution on the base protons.
Base-boronated dinucleotides: synthesis and effect of N7-cyanoborane substitution on the base protons.
复制标题
碱基硼化二核苷酸：N7-氰基硼烷取代对碱基质子的合成和影响。
DOI：
10.1093/nar/24.11.2150
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发表时间：
1996
影响因子：
14.9
通讯作者：
Shaw,BR
中科院分区：
文献类型：
--
作者：
Hasan,A;Li,H;Tomasz,J;Shaw,BR
Boron-modified nucleic acids comprise a new set of DNA mimics that have potential biological and therapeutic applications. A series of nine dinucleotides containing N7-cyanoborane-2′-deoxyguanosine (7bdG) at the 3′, 5′ or both positions of the phosphodiester linkage have been synthesized using solution phase phosphoramidite chemistry. Fmoc was used as the 5′-protecting group because of incompatibility of the cyanoborane moiety with 5′-DMT cations generated during the deprotection step. The presence of the cyanoborane group was confirmed on the basis of Fab-MS and1H NMR spectroscopy. The H-8 proton of7bdG in the dinucleotides shifted 0.35-0.80 p.p.m. downfield relative to that of unmodified dG. A comparison of the D2O exchange kinetics of the H-8 proton at 60°C showed that H-8 of7bdG is very labile relative to unmodified dG, indicating that the N7-cyanoborane modification increases the acidity of the H-8 proton of7bdG. These studies illustrate the feasibility of synthesizing boron-containing oligonucleotides which are modified at the N7-guanine to block Hoogsteen pairing in the DNA major groove.
