通过改良的磷酸三酯法合成环状寡核苷酸。
Synthesis of cyclic oligonucleotides by a modified phosphotriester approach.
作者信息
de Vroom E, Broxterman H J, Sliedregt L A, van der Marel G A, van Boom J H
机构信息
Gorlaeus Laboratory, Leiden, The Netherlands.
出版信息
Nucleic Acids Res. 1988 May 25;16(10):4607-20. doi: 10.1093/nar/16.10.4607.
Abstract
Evidence will be presented to show that the allyl group is suitable for the protection of a 3'-terminal phosphodiester function. The latter will be demonstrated by the synthesis, via a phosphotriester approach, of two cyclic tetraribonucleotides [r(AAAA) and r(UAMe2UAMe2)], two cyclic hexadeoxyribonucleotides [d(CGCGCG) and d(TAAAAA)] and a cyclic octadeoxyribonucleotide [d(CGTGCGTG)].
摘要
将提供证据表明烯丙基适用于保护3'-末端磷酸二酯功能。这将通过磷酸三酯法合成两种环状四核糖核苷酸[r(AAAA)和r(UAMe2UAMe2)]、两种环状十六脱氧核糖核苷酸[d(CGCGCG)和d(TAAAAA)]以及一种环状十八脱氧核糖核苷酸[d(CGTGCGTG)]来证明。
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本文引用的文献
1
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2
RNA polymerase: linear competitive inhibition by bis-(3' to 5')-cyclic dinucleotides,NpNp.RNA聚合酶：双（3'至5'）环二核苷酸NpNp的线性竞争性抑制作用
Nucleic Acids Res. 1982 Sep 25;10(18):5637-47. doi: 10.1093/nar/10.18.5637.
3
Chemical synthesis of a messenger ribonucleic acid fragment: AUGUUCUUCUUCUUCUUC.信使核糖核酸片段的化学合成：AUGUUCUUCUUCUUCUUC
Biochemistry. 1982 Mar 2;21(5):1009-18. doi: 10.1021/bi00534a028.
4
Flow of information in the light-triggered cyclic nucleotide cascade of vision.视觉中光触发的环核苷酸级联反应中的信息流动。
Proc Natl Acad Sci U S A. 1981 Jan;78(1):152-6. doi: 10.1073/pnas.78.1.152.
5
Synthesis of short RNA fragments by the benzotriazolyl phosphotriester approach.通过苯并三唑基磷酸三酯法合成短RNA片段。
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6
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