Synthesis of two 8-[(anthraquinone-2-yl)-linked]-2′-deoxyadenosine 3′-benzyl hydrogen phosphates for studies of photoinduced hole transport in DNA

被引:18
作者
Abou-Elkhair, RAI [1 ]
Netzel, TL [1 ]
机构
[1] Georgia State Univ, Dept Chem, Atlanta, GA 30302 USA
关键词
photoinduced electron transfer; modified DNA; modified nucleoside; anthraquinone-modified 2 '-deoxyadenosine; 2-ethynylanthraquinone; anthraquinone-2 '-deoxyadenosine phosphate;
D O I
10.1081/NCN-200051894
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
The challenge in working with anthraquinone-2'-deoxyadenosine (AQ-dA) conjugates is that they are insoluble in water and only sparingly soluble in most organic solvents. However, water-soluble AQ-dA conjugates with short linkers are required for study of their electrochemical and intramolecular electron transfer Properties in this solvent prior to their use in laser kinetics investigations of photoinduced hole (cation) transport in DNA. This article first describes the synthesis Of a water-soluble, ethynyl-linked AQ-dA conjugate, 8-[(anthraquinone-2-yl)ethynyl]-2'-deoxyadenosine 3'-benzyl hydrogen phosphate, based on initial formation of a 5-O-(4,4'-dimethoxytrityl) (5'-O-DMTr) intermediate. Because intended H-2 over Pd/C reduction of the ethyryl linker in 5-O-DMTr-protected 2'-deoxyadenosines cleaves the DMTr protecting group and precipitates multiple side products, this work also describes the synthesis Of an ethylenyl-linked AQ-dA conjugate, 8-[2-(anthraquinone-2-yl)ethyl]-2'-deoxyadenosine 3'-benzyl hydrogen phosphate, starting with a 5-O-tert-butyldiphenylsilyl protecting group.
引用
收藏
页码:85 / 110
页数:26
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