6-氯嘌呤-2'-脱氧核糖核苷5'-二甲氧基三苯甲基3'-(2-氰基乙基-N,N-二异丙基氨基)亚磷酰胺的半合成及其在荧光标记寡核苷酸合成中的应用。
Semisynthesis of 6-chloropurine-2'-deoxyriboside 5'-dimethoxytrityl 3'-(2-cyanoethyl-N,N-diisopropylamino)phosphoramidite and its use in the synthesis of fluorescently labeled oligonucleotides.
作者信息
Uddin Md Jashim, Schulte Michael I, Maddukuri Leena, Harp Joel, Marnett Lawrence J
机构信息
A. B. Hancock Jr. Memorial Laboratory for Cancer Research, Departments of Biochemistry, Chemistry, and Pharmacology, Vanderbilt Institute of Chemical Biology, Vanderbilt University School of Medicine, Nashville, TN 37232-0146, USA.
出版信息
Nucleosides Nucleotides Nucleic Acids. 2010 Nov;29(11):831-40. doi: 10.1080/15257770.2010.530332.
An efficient enzymatic synthesis of 6-chloropurine-2'-deoxyriboside from the reaction of 6-chloropurine with 2'-deoxycytidine catalyzed by nucleoside-2'-deoxyribosyltransferase (E.C. 2.4.2.6) followed by chemical conversion into the 5'-dimethoxytrityl 3'-(2-cyanoethyl-N,N-diisopropylamino) phosphoramidite derivative is described. The phosphoramidite derivative was incorporated site-specifically into an oligonucleotide and used for the introduction of a tethered tetramethylrhodamine-cadaverine conjugate. The availability of an efficient route to 6-chloropurine-2'-deoxyriboside 5'-dimethoxytrityl 3'-(2-cyanoethyl-N,N-diisopropylamino)phosphoramidite enables the facile synthesis of oligonucleotides containing a range of functional groups tethered to deoxyadenosine residues.
描述了一种高效的酶促合成方法，即通过核苷-2'-脱氧核糖基转移酶（E.C. 2.4.2.6）催化6-氯嘌呤与2'-脱氧胞苷反应生成6-氯嘌呤-2'-脱氧核糖苷，然后通过化学转化为5'-二甲氧基三苯甲基3'-(2-氰基乙基-N,N-二异丙基氨基)亚磷酰胺衍生物。该亚磷酰胺衍生物被位点特异性地掺入寡核苷酸中，并用于引入连接的四甲基罗丹明-尸胺缀合物。有了一条通往6-氯嘌呤-2'-脱氧核糖苷5'-二甲氧基三苯甲基3'-(2-氰基乙基-N,N-二异丙基氨基)亚磷酰胺的有效路线，就能够轻松合成含有一系列连接到脱氧腺苷残基上的官能团的寡核苷酸。
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