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The Behaviour of 2′-Deoxy-2′-Fluorouridine Incorporated into Oligonucleotides by the Phosphoramidite Approach

 

作者: A. Krug,   T.S. Oretskaya,   E.M. Volkov,   D. Cech,   Z.A. Shabarova,   A. Rosenthal,  

 

期刊: Nucleosides and Nucleotides  (Taylor Available online 1989)
卷期: Volume 8, issue 8  

页码: 1473-1483

 

ISSN:0732-8311

 

年代: 1989

 

DOI:10.1080/07328318908048855

 

出版商: Taylor & Francis Group

 

数据来源: Taylor

 

摘要:

2′-Deoxy-2′-fluorouridine has been chemically incorporated into an oligodeoxynucleotide of the structure 5′ACGGAX 3′ (X=U(2′-F)) using the phosphoramidite method and the behaviour of the product has been studied. 5′-O-Monomethoxytrityl-2′-deoxy-2′-fluorouridine was fixed on silica gel at the 3′-end and the chain elongated on a DNA-synthesizer using nucleoside methoxyphosphoramidites. After alkaline work-up two products were observed. One was found to be the desired fluoro containing hexamer, whereas the other corresponds to an araU-hexamer (X=arabino-furanosyluridine). The latter compound is supposed to be a product of alkaline hydrolysis of the C-2′-F-bond. The oligomers containing 2′-fluoro- and ara-U at their 3′-end were chemically sequenced by a solid phase method on CCS-paper which confirmed the right primary structure.

 

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