Synthesis of 4'-Selenoribonucleosides, the Building Blocks of 4'-SelenoRNA, Using a Hypervalent Iodine.
Curr Protoc Nucleic Acid Chem
; 70: 1.40.1-1.40.21, 2017 09 18.
Article
em En
| MEDLINE
| ID: mdl-28921498
Herein is described a detailed protocol for the synthesis of 4'-selenoribonucleoside derivatives that involves the use of a hypervalent iodine species. These derivatives are versatile units for the preparation of 4'-selenoRNA. Large-scale synthesis of a 4-selenosugar starting from D-ribose is achieved in eight steps, including a final chromatographic purification. The resulting 4-selenosugar is then subjected to the one-pot Pummerer-like reaction using hypervalent iodine in the presence of silylated nucleobases. The reaction with silylated uracil affords the desired 4'-selenouridine derivatives with excellent ß-selectivity and in good yield. Conversely, when purine nucleobases are used in the Pummerer-like reaction, N7 4'-selenoribonucleoside isomers are obtained alongside the desired N9 isomers. However, the undesired N7 isomers can be converted to the desired N9 ones under acidic conditions. © 2017 by John Wiley & Sons, Inc.
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Texto completo:
1
Bases de dados:
MEDLINE
Assunto principal:
Ribonucleosídeos
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Compostos Organosselênicos
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Iodetos
Idioma:
En
Revista:
Curr Protoc Nucleic Acid Chem
Ano de publicação:
2017
Tipo de documento:
Article
País de afiliação:
Japão