Modification of guanine bases by nucleoside phosphoramidite reagents during the solid phase synthesis of oligonucleotides.
Modification of guanine bases by nucleoside phosphoramidite reagents during the solid phase synthesis of oligonucleotides.
复制标题
在寡核苷酸的固相合成过程中，核苷亚磷酰胺试剂对鸟嘌呤碱基进行修饰。
DOI：
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发表时间：
1985
影响因子：
14.9
通讯作者：
K. K. Ogilvie
中科院分区：
文献类型：
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作者：
R. Pon;M. Damha;K. K. Ogilvie
已经发现核苷3 '-亚磷酰胺和氯代亚磷酸酯试剂与鸟嘌呤的内酰胺官能团反应。当在自动固相合成仪中制备含有大量鸟嘌呤碱基的寡脱氧核糖核苷酸时，该反应导致不令人满意的结果。鸟嘌呤修饰是不稳定的，并导致脱嘌呤和链断裂。这种副反应可以通过保护O 6-位来消除。一种新的O 6-p-硝基苯乙基脱氧鸟苷亚磷酰胺衍生物，8，用于制备序列含有多达24个鸟嘌呤碱基，大大改善了结果。一个hexatriacontanucleotide，d（CGCGGGGTGGAGCAGCCTGGTAGCTCGTCGGGCTCA），也可以使用O 6-保护的脱氧鸟苷核苷制备。
Nucleoside 3'-phosphoramidite and chlorophosphite reagents have been found to react with the lactam function of guanine. This reaction caused unsatisfactory results when oligodeoxyribonucleotides containing a large number of guanine bases were prepared in an automated solid phase synthesizer. The guanine modification is unstable, and leads to depurination and chain cleavage. This side reaction can be eliminated by protecting the O6-position. A new O6-p-nitrophenylethyldeoxyguanosine phosphoramidite derivative, 8, was used to prepare sequences containing up to 24 guanine bases with greatly improved results. A hexatriacontanucleotide, d(CGCGGGGTGGAGCAGCCTGGTAGCTCGTCGGGCTCA), was also prepared using O6-protected deoxyguanosine nucleosides.