受保护的5'-巯基-2',5'-二脱氧核糖核苷-3'-O-亚磷酰胺的合成；5'-巯基寡脱氧核糖核苷酸的用途。
The synthesis of protected 5'-mercapto-2',5'-dideoxyribonucleoside-3'-O-phosphoramidites; uses of 5'-mercapto-oligodeoxyribonucleotides.
作者信息
Sproat B S, Beijer B, Rider P, Neuner P
出版信息
Nucleic Acids Res. 1987 Jun 25;15(12):4837-48. doi: 10.1093/nar/15.12.4837.
Abstract
The syntheses of the four novel, base protected 5'-(S-triphenylmethyl)mercapto-2',5'-dideoxyribonucleoside-3 '-O-(2-cyanoethyl N,N-diisopropylphosphoramidites) are described. These compounds have been used to prepare 5'-(S-triphenylmethyl) mercapto-oligodeoxyribonucleotides, which are readily purified by reversed phase h.p.l.c., owing to the highly lipophilic trityl group. After cleavage of the S-trityl group by silver or mercuric ions, the free thiol moiety can be coupled to a wide variety of reagents, generating very useful probes. Fluorescent labelled 5'-mercapto-oligodeoxyribonucleotides are being used for automated DNA sequencing without radioactivity, and heavy metal labelled 5'-mercapto-oligonucleotides will be used in X-ray crystallography.
摘要
本文描述了四种新型的、碱基保护的5'-（S-三苯甲基）巯基-2'，5'-二脱氧核糖核苷-3'-O-（2-氰基乙基N，N-二异丙基磷酰胺）的合成方法。这些化合物已被用于制备5'-（S-三苯甲基）巯基-寡脱氧核糖核苷酸，由于三苯甲基基团具有高度亲脂性，这些寡核苷酸很容易通过反相高效液相色谱法进行纯化。在用银离子或汞离子裂解S-三苯甲基基团后，游离的巯基部分可以与多种试剂偶联，从而生成非常有用的探针。荧光标记的5'-巯基-寡脱氧核糖核苷酸正被用于无放射性的自动化DNA测序，而重金属标记的5'-巯基-寡核苷酸将用于X射线晶体学研究。
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The synthesis of protected 5'-mercapto-2',5'-dideoxyribonucleoside-3'-O-phosphoramidites; uses of 5'-mercapto-oligodeoxyribonucleotides.受保护的5'-巯基-2',5'-二脱氧核糖核苷-3'-O-亚磷酰胺的合成；5'-巯基寡脱氧核糖核苷酸的用途。
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