异丙氧基乙酰基用于在寡脱氧核糖核苷酸及其三酯类似物的固相合成过程中方便地进行碱基保护。
The isopropoxyacetic group for convenient base protection during solid-support synthesis of oligodeoxyribonucleotides and their triester analogs.
作者信息
Uznanski B, Grajkowski A, Wilk A
机构信息
Polish Academy of Sciences, Department of Bioorganic Chemistry, Lodz.
出版信息
Nucleic Acids Res. 1989 Jun 26;17(12):4863-71. doi: 10.1093/nar/17.12.4863.
Abstract
Isopropoxyacetic anhydride was successfully used for protection of exoaminofunctions of 2'-deoxyadenosine, -guanosine and -cytidine. N-isopropoxyacetylated nucleosides are stable under the conditions of the synthesis of oligodeoxyribonucleotides on the solid support. Removal of N-isopropoxyacetyl is much faster than that of commonly used benzoyl or isobutyryl groups viz. it is completed within the operation of cleavage of the oligodeoxyribonucleotide from the solid support. This observation enabled synthesis of -OCH2CH3 and -OCH2CF3 triesters, which hydrolyse partially or completely when standard deprotection conditions are applied.
摘要
异丙氧基乙酸酐已成功用于保护2'-脱氧腺苷、-鸟苷和-胞苷的氨基外官能团。N-异丙氧基乙酰化核苷在固体支持物上合成寡脱氧核糖核苷酸的条件下是稳定的。N-异丙氧基乙酰基的去除比常用的苯甲酰基或异丁酰基快得多，即在从固体支持物上切割寡脱氧核糖核苷酸的操作过程中即可完成。这一发现使得-OCH2CH3和-OCH2CF3三酯得以合成，当应用标准脱保护条件时，它们会部分或完全水解。
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本文引用的文献
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2
Alkyl phosphotriester modified oligodeoxyribonucleotides. V. Synthesis and absolute configuration of Rp and Sp diastereomers of an ethyl phosphotriester (Et) modified EcoRI recognition sequence, d[GGAA(Et)TTCC]. A synthetic approach to regio- and stereospecific ethylation-interference studies.烷基磷酸三酯修饰的寡脱氧核糖核苷酸。V. 磷酸三乙酯（Et）修饰的EcoRI识别序列d[GGAA(Et)TTCC]的Rp和Sp非对映异构体的合成及绝对构型。区域和立体特异性乙基干扰研究的合成方法。
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