用于在寡脱氧核苷酸合成中保护脱氧腺苷N6-氨基的环状二酰基基团。
Cyclic diacyl groups for protection of the N6-amino group of deoxyadenosine in oligodeoxynucleotide synthesis.
作者信息
Kume A, Iwase R, Sekine M, Hata T
出版信息
Nucleic Acids Res. 1984 Nov 26;12(22):8525-38. doi: 10.1093/nar/12.22.8525.
Abstract
Three kinds of substituted phthaloyl groups and a succinyl group were introduced onto the N6-amino function of deoxyadenosine derivatives. Among them, the succinyl group was found to be the most effective for prevention of depurination upon detritylation in acidic media and the most stable in basic media. Protection of the N6-amino function of 5'-O-dimethoxytrityldeoxyadenosine and introduction of a succinate linker into the 3'-hydroxyl were achieved simultaneously by a one-step reaction with succinic anhydride. A tetradeoxyribonucleotide, dTpTpTpA containing a 3'-terminal deoxyadenosine was successfully synthesized on a polystyrene support via the phosphotriester method.
摘要
将三种取代的邻苯二甲酰基和一个琥珀酰基引入到脱氧腺苷衍生物的N6-氨基官能团上。其中，发现琥珀酰基对于在酸性介质中脱三苯甲基时防止脱嘌呤最为有效，并且在碱性介质中最稳定。通过与琥珀酸酐的一步反应，同时实现了5'-O-二甲氧基三苯甲基脱氧腺苷的N6-氨基官能团的保护以及在3'-羟基中引入琥珀酸连接基。通过磷酸三酯法在聚苯乙烯载体上成功合成了含有3'-末端脱氧腺苷的四脱氧核糖核苷酸dTpTpTpA。
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