New reagents and methods for the synthesis of internal and 3′-labeled DNA

被引:14
作者
Lyttle, MH [1 ]
Walton, TA [1 ]
Dick, DJ [1 ]
Carter, TG [1 ]
Beckman, JH [1 ]
Cook, RM [1 ]
机构
[1] Biosearch Technol Inc, Novato, CA 94949 USA
关键词
D O I
10.1021/bc020011c
中图分类号
Q5 [生物化学];
学科分类号
071010 ; 081704 ;
摘要
The syntheses of two new nucleoside phosphoramidites containing a hydroxyl functionality masked by a levulinate protecting group are presented; N-4-(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 parameters for 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 chain attached at the 5 position, was also revisited using new techniques developed for 3.
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页码:1146 / 1154
页数:9
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