New Reagents and Methods for the Synthesis of Internal and 3'-Labeled DNA

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• 作者：Matthew H. Lyttle ; Troy A. Walton ; Daren J. Dick ; Timothy G. Carter ; Jacob H. Beckman ; and Ronald M. Cook
• 刊名：Bioconjugate Chemistry
• 出版年：2002
• 出版时间：September 2002
• 年：2002
• 卷：13
• 期：5
• 页码：1146 - 1154
• 全文大小：135K
• 年卷期：v.13,no.5(September 2002)
• ISSN：1520-4812

文摘

The syntheses of two new nucleoside phosphoramidites containing a hydroxyl functionality maskedby a levulinate protecting group are presented; N⁴-(2-(ethylene glycol-2-levulinate)ethyl)-5-methyl-5'-(4,4'-dimethoxytrityl)-3'-O-(2-cyanoethyldiisopropylphosphoramidite)-2'-deoxycytidine 1 and 5-(N-(6-O-levulinoyl-1-aminohexyl)-3(E)-acrylamido)-5'-(4,4'-dimethoxytrityl)-3'-(2-cyanoethyldiisopropylphosphoramidite)-2'-deoxyuridine 3. Optimization of solid-phase-supported synthetic parametersfor incorporation of these into DNA, removal of the levulinate group by exposure to dilute hydrazine,and subsequent attachment of dye labels is described. Synthesis of the known compound 5-(N-(6-trifluoroacetylaminohexyl)-3(E)-acrylamido)-5'-(4,4'-dimethoxytrityl)-3'-(2-cyanoethyldiisopropylphosphoramidite)-2'-deoxyuridine 2 (1), containing a masked amine at the end of an alkyl chainattached at the 5 position, was also revisited using new techniques developed for 3.