合成与大肠杆菌16S核糖体RNA 3'-末端序列相同或相似的寡核苷酸：通过磷酸三酯中间体制备m-6-2-A-C-C-U-C-C和A-C-C-U-C-m-4-2C
Synthesis of oligonucleotides with sequences identical with or analogous to the 3'-end of 16S ribosomal RNA of Escherichia coli: preparation of m-6-2-A-C-C-U-C-C and A-C-C-U-C-m-4-2C via phosphotriester intermediates.
作者信息
van Boom J H, Burgers P M, van der Marel G, Wille G
出版信息
Nucleic Acids Res. 1977 Mar;4(3):747-59. doi: 10.1093/nar/4.3.747.
Abstract
The synthesis of two fully-protected hexanucleotides (11a and 11b) via a phosphotriester approach, which is based on the use of two types of protecting groups for the internucleotide linkages, i.e. one 2,2,2-tribromo-ethyl at the 5'-terminus and four 2-chlorophenyl groups for the remaining linkages, is reported. The hexanucleotides 11a and 11b, assembled via a block-wise two-step phosphotriester method, can be deblocked conveniently to give the two hexamers 12a and 12b containing only 3'leads to5' internucleotide linkages.
摘要
报道了通过磷酸三酯法合成两种完全保护的六核苷酸（11a和11b），该方法基于对核苷酸间连接使用两种保护基团，即5'-末端的一个2,2,2-三溴乙基和其余连接的四个2-氯苯基。通过逐步两步磷酸三酯法组装的六核苷酸11a和11b可以方便地脱保护，得到仅含有3'到5'核苷酸间连接的两种六聚体12a和12b。
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本文引用的文献
1
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Tetrahedron. 1967 May;23(5):2301-13. doi: 10.1016/0040-4020(67)80067-x.
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
The use of beta,beta,beta-tribromoethyl chloroformate for the protection of nucleoside hydroxyl groups.
J Org Chem. 1968 Sep;33(9):3589-93. doi: 10.1021/jo01273a052.
4
Synthesis of oligonucleotides by use of phosphoric triesters.
Angew Chem Int Ed Engl. 1967 Aug;6(8):695-7. doi: 10.1002/anie.196706951.
5
A protein-nucleic acid crosslink in 30S ribosomes.30S核糖体中的一种蛋白质-核酸交联物。
Biochem Biophys Res Commun. 1973 Apr 16;51(4):932-8. doi: 10.1016/0006-291x(73)90016-8.
6
Deoxy oligonucleotide synthesis via the triester method.通过三酯法合成脱氧寡核苷酸。
J Org Chem. 1973 Jan 26;38(2):245-50. doi: 10.1021/jo00942a011.
7
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8
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