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O-β-D-呋喃核糖基（1”→2'）核糖核苷及寡核苷酸的合成与结构研究

Studies on synthesis and structure of O-beta-D-ribofuranosyl(1"-->2')ribonucleosides and oligonucleotides.

作者信息

Markiewicz W T, Niewczyk A, Gdaniec Z, Adamiak D A, Dauter Z, Rypniewski W, Chmielewski M

机构信息

Institute of Bioorganic Chemistry, Polish Academy of Sciences, Poznań, Poland.

出版信息

Nucleosides Nucleotides. 1998 Jan-Mar;17(1-3):411-24. doi: 10.1080/07328319808005187.

DOI:10.1080/07328319808005187
PMID:9708355
Abstract

Minor nucleosides found in several eukaryotic initiator tRNASiMet, O-beta-D-ribofuranosyl(1"-->2')adenosine and -guanosine (Ar and Gr), as well as their pyrimidine analogues, were obtained from N-protected 3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)ribonucle osides and 1-O-acetyl-2,3,5-tri-O-benzoyl-beta-D-ribofuranose in the presence of tin tetrachloride in 1,2-dichloroethane. A crystal structure has been solved for 2'-O-ribosyluridine. The 3'-phosphoramidites of protected 2'-O-ribosylribonucleosides were prepared as the reagents for 2'-O-ribofuranosyloligonucleotides synthesis. O-beta-D-Ribofuranosyl(1"-->2')adenylyl(3'-->5')guanosine (ArpG) was obtained and its structure was analysed by NMR spectroscopy.

摘要

在几种真核起始甲硫氨酸转运核糖核酸（tRNASiMet）中发现的微量核苷、O-β-D-呋喃核糖基（1"→2'）腺苷和鸟苷（Ar和Gr），以及它们的嘧啶类似物，是在四氯化锡存在下，于1,2-二氯乙烷中，由N-保护的3',5'-O-（1,1,3,3-四异丙基二硅氧烷-1,3-二基）核糖核苷和1-O-乙酰基-2,3,5-三-O-苯甲酰基-β-D-呋喃核糖制备得到的。已解析出2'-O-核糖基尿苷的晶体结构。制备了受保护的2'-O-核糖基核糖核苷的3'-亚磷酰胺，作为合成2'-O-呋喃核糖基寡核苷酸的试剂。获得了O-β-D-呋喃核糖基（1"→2'）腺苷酰基（3'→5'）鸟苷（ArpG），并通过核磁共振光谱对其结构进行了分析。

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