Synthesis and characterization of ferrocene-labeled oligodeoxynucleotides

被引:44
作者
Beilstein, AE [1 ]
Grinstaff, MW [1 ]
机构
[1] Duke Univ, Dept Chem, Paul M Gross Chem Lab, Durham, NC 27708 USA
关键词
ferrocene; oligodeoxynucleotides; on-column; solid-phase; cross-coupling; synthesis; bioorganometallic chemistry;
D O I
10.1016/S0022-328X(01)00943-3
中图分类号
O61 [无机化学];
学科分类号
070301 [无机化学]; 081704 [应用化学];
摘要
Using a facile on-column derivatization procedure, oligodeoxynucleotides (ODNs) are labeled with a ferrocene derivative at specific sites. A Sonagashira cross-coupling reaction, using Pd(PPh3)(4) and CuI, links ferrocene propargylamide to a halogenated base, such as 2'-deoxy-5-iodouridine or 8-bromo-2'-deoxyadenosine, which has been previously incorporated in the ODN strand. The structure and stability of the DNA duplex are not significantly altered after site-specific labeling with ferrocene, as demonstrated by T-m and CD spectroscopy. (C) 2001 Elsevier Science B.V. All rights reserved.
引用
收藏
页码:398 / 406
页数:9
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