5-Fluoro-4-thiouridine phosphoramidite: New synthon for introducing photoaffinity label into oligodeoxynucleotides

The synthesis of phosphoramidite of 5-fluoro-4-thio-2′- O-methyluridine is described. An appropriate set of protecting groups was optimized including the 4-thio function introduced via 4-triazolyl as the 4-(2-cyanoethyl)thio derivative, and the t-butyldimethyl silyl for 2′ and 3′ hydroxyl protection...

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Bibliographic Details
Published in:Bioorganic & medicinal chemistry 2011-10, Vol.19 (20), p.6098-6106
Main Authors: Milecki, Jan, Nowak, Joanna, Skalski, Bohdan, Franzen, Stefan
Format: Article
Language:English
Subjects:
5-Fluoro-4-thiouridine
Analytical, structural and metabolic biochemistry
automation
Biological and medical sciences
Carbohydrates. Nucleosides and nucleotides
chemical reactions
Chemistry
Exact sciences and technology
Fundamental and applied biological sciences. Psychology
General aspects, investigation methods
Nucleic acids
Nucleosides, nucleotides and oligonucleotides
oligodeoxyribonucleotides
Oligodeoxyribonucleotides - chemical synthesis
Oligodeoxyribonucleotides - chemistry
Oligonucleotides
Oligonucleotides - chemical synthesis
Oligonucleotides - chemistry
Organic chemistry
Organophosphorus Compounds - chemical synthesis
Organophosphorus Compounds - chemistry
Phosphoramidite
Photoaffinity Labels - chemical synthesis
Photoaffinity Labels - chemistry
photochemistry
Photocrosslink
Preparations and properties
synthesis
Thiouridine - analogs & derivatives
Thiouridine - chemical synthesis
Thiouridine - chemistry
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Description
Summary:The synthesis of phosphoramidite of 5-fluoro-4-thio-2′- O-methyluridine is described. An appropriate set of protecting groups was optimized including the 4-thio function introduced via 4-triazolyl as the 4-(2-cyanoethyl)thio derivative, and the t-butyldimethyl silyl for 2′ and 3′ hydroxyl protection, enabling efficient synthesis of the phosphoramidite. These protecting groups prevented unwanted side reactions during oligonucleotide synthesis. The utility of the proposed synthetic route was proven by the preparation of several oligonucleotides via automated synthesis. Photochemical experiments confirmed the utility of the synthon.
ISSN:0968-0896
1464-3391
DOI:10.1016/j.bmc.2011.08.035