几种缩合试剂磺化用于化学合成脱氧寡核糖核苷酸的效率、问题及其机制的研究
A study of the efficiency and the problem of sulfonation of several condensing reagents and their mechanisms for the chemical synthesis of deoxyoligoribonucleotides.
作者信息
Seth A K, Jay E
出版信息
Nucleic Acids Res. 1980 Nov 25;8(22):5445-59. doi: 10.1093/nar/8.22.5445.
Abstract
The efficiencies and problems of sulfonation of several condensing reagents for deoxyoligoribonucleotide synthesis have been studied. While 2,4,6-triisopropylbenzenesulfonyl chloride (TPSC1) gave very low yield and slow rate of coupling, the new 1:3 mixture of TPSC1 and tetrazole afforded excellent yield and extremely fast rate of reaction with the lowest rate of sulfonation. The difference and advantages of this mixture over triisopropylbenzenesulfonyl tetrazole (TPSTe) and mesitylenesulfonyl tetrazole (MSTe) are discussed. Mechanisms for the coupling reactions with these condensing reagents to account for the difference in their rates and yields of coupling are discussed.
摘要
研究了几种用于脱氧寡核糖核苷酸合成的缩合试剂磺化反应的效率和问题。虽然2,4,6-三异丙基苯磺酰氯（TPSC1）的产率很低且偶联速率很慢，但新的TPSC1与四氮唑1:3混合物的产率极高，反应速率极快，磺化速率最低。讨论了该混合物相对于三异丙基苯磺酰四氮唑（TPSTe）和均三甲苯磺酰四氮唑（MSTe）的差异和优势。讨论了与这些缩合试剂进行偶联反应的机理，以解释它们偶联速率和产率的差异。
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本文引用的文献
1
The case of sulfonation in the chemical synthesis of oligonucleotides.寡核苷酸化学合成中的磺化反应实例。
Nucleic Acids Res. 1980 May 24;8(10):2301-5. doi: 10.1093/nar/8.10.2301.
2
Studies on polynucleotides. LI. Syntheses of the 64 possible ribotrinucleotides derived from the four major ribomononucleotides.多核苷酸的研究。第一部分。由四种主要核糖单核苷酸衍生而来的64种可能的核糖三核苷酸的合成。
J Am Chem Soc. 1966 Feb 20;88(4):819-29. doi: 10.1021/ja00956a039.
3
Total synthesis of the gene for an alanine transfer ribonucleic acid from yeast.酵母丙氨酸转移核糖核酸基因的全合成
Nature. 1970 Jul 4;227(5253):27-34. doi: 10.1038/227027a0.
4
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Nucleic Acids Res. 1977 Aug;4(8):2757-65. doi: 10.1093/nar/4.8.2757.
5
6
A synthetic tyrosine suppressor tRNA gene with an altered promoter sequence. Its cloning and relative expression in vivo.一个具有改变启动子序列的合成酪氨酸抑制tRNA基因。其克隆及在体内的相对表达。
J Biol Chem. 1979 Nov 10;254(21):10803-10.
7
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8
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