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一种通过改进的新亚磷酸酯法合成中等长度寡脱氧核糖核苷酸的简便方法。

A convenient approach to the synthesis of medium size oligodeoxyribonucleotides by improved new phosphite method.

作者信息

Hosaka H, Suzuki Y, Sato H, Gug-Kim S, Takaku H

机构信息

Department of Industrial Chemistry, Chiba Institute of Technology, Japan.

出版信息

Nucleic Acids Res. 1991 Jun 11;19(11):2935-40. doi: 10.1093/nar/19.11.2935.

Abstract

Improvement of the new phosphite method for the synthesis of oligodeoxyribonucleotides using the deoxyribonucleoside 3'-bis(1,1,1,3,3,3- hexafluoro-2-propyl) phosphite unit has been carried out via the hydrolysis and capping steps, without any side reaction products. The new phosphite unit and capping agent, bis(1,1,1,3,3,3-hexafluoro-2-propyl)-2-propyl phosphite, is readily activated by N-methylimdazole under very mild condition on a solid support. This operation involves a one pot reaction, which is an advantage over both the phosphite and H- phosphonate approaches. The mechanism of internucleotidic bond formation of the new phosphite method is also discussed.

摘要

通过水解和封端步骤对使用亚磷酸脱氧核苷3'-双(1,1,1,3,3,3-六氟-2-丙基)亚磷酸酯单元合成寡脱氧核糖核苷酸的新亚磷酸酯方法进行了改进,未产生任何副反应产物。新的亚磷酸酯单元和封端剂双(1,1,1,3,3,3-六氟-2-丙基)-2-丙基亚磷酸酯在非常温和的条件下于固体支持物上很容易被N-甲基咪唑活化。该操作涉及一锅反应,这是相对于亚磷酸酯法和H-亚膦酸酯法的一个优势。还讨论了新亚磷酸酯法中核苷酸间键形成的机制。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/865c/328254/86b495f2e816/nar00091-0127-a.jpg

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