Procedure to obtain the 3′,5′-di-O-acetyl-5-formyl-2′-deoxyuridine.
Many types of DNA damage have been identified in cells exposed to ionizing radiation and oxidizing agents. 5-Formyl-2′-deoxyuridine has been identified in cells exposed to ionizing radiations and oxidizing agents and was recognized as a potentially mutagenic compound. Also, it can be an important an...
| Publicado en: | Revista CENIC Ciencias Quimicas Vol. 38; no. 1; pp. 237 - 243 |
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| Autores principales: | , , , , |
| Formato: | Artículo |
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Centro Nacional de Investigaciones Cientificas
2007
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| Materias: | |
| Acceso en línea: | Ver este registro en EBSCOhost |
| fields | @attributes: recordID: 1 pdfLink: plink: https://search.ebscohost.com/login.aspx?direct=true&db=lth&AN=31142811&site=ehost-live header: @attributes: shortDbName: lth uiTerm: 31142811 longDbName: MedicLatina uiTag: AN controlInfo: bkinfo: jinfo: jid: 10158553 UF0 jtl: Revista CENIC Ciencias Quimicas issn: 10158553 maglogo: N pubinfo: dt: 2007 vid: 38 iid: 1 pid: 21205 pub: Centro Nacional de Investigaciones Cientificas artinfo: ui: 31142811 ppf: 237 ppct: 6 formats: fmt: @attributes: type: P size: 244KB tig: atl: Procedure to obtain the 3′,5′-di-O-acetyl-5-formyl-2′-deoxyuridine. aug: au: Sablón-Carrazana, Marquiza Jiménez-Alemán, Guillermo Pérez Perera, Rafaela Vélez-Castro, Hermán Rodríguez-Tanty, Chryslaine affil: Molecular Biology Department, Neurosciences Center, 25 Avenue No. 15202, Postal Code 12100, Havana City, P.O. Box 6414, Cuba Chemistry Deparment, Center of Pharmaceutical Chemistry, 200 Street and 21 Avenue, Atabey su: Nucleosides Hydroxyl group Uridine DNA damage Biochemical genetics Oxidizing agents Ionizing radiation sug: subj: Nucleosides Hydroxyl group Uridine DNA damage Biochemical genetics Oxidizing agents Ionizing radiation keyword: 5-formyl-2′-deoxyuridine Jones reagent nucleoside analogues synthesis 5-formil-2′-desoxiuridina reactivo de Jones síntesis de análogos de nucleósidos ab: Many types of DNA damage have been identified in cells exposed to ionizing radiation and oxidizing agents. 5-Formyl-2′-deoxyuridine has been identified in cells exposed to ionizing radiations and oxidizing agents and was recognized as a potentially mutagenic compound. Also, it can be an important and versatile intermediate for the synthesis of various 5-substituted 2′-deoxyuridine. In this work, a convenient method is presented for the conversion of 2′-deoxythymidine to 3′,5′-di-O-acetyl-5-formyl-2′-deoxyuridine (4) via halogenation, hydrolysis and oxidation of 3′,5′-di-O-acetyl-2′-deoxythymidine (1) intermediate. Studies to select the suitable brominating, hydrolyzing and oxidizing agents were performed. Thus, molecular bromine and N-bromosuccinimide (NBS) were essayed in the halogenation step, and NBS permitted to obtain the desired product, 5-bromomethyl)-3′,5′-di-O-acetyl-2′-deoxyuridine (2), and only trace of dibromide compound. Several hydrolyse procedures were evaluated to afford the hydroxymethyl 3′,5′-di-O-acetyl-2′-deoxyuridine (3) from 2 and a neutral procedure with water was selected for this step. In the oxidation step, a comparative analysis between the active manganese dioxide and the Jones reagent was carried out for establishing the optimal conditions to give 4. The Jones reagent was successfully used to oxidize the allylic alcohol group of the nucleoside to formyl group through a method herein more practical since it is easier and more reproducible. Numerosos tipos de daños al ADN han sido identificados en células expuestas a radiación ionizante y a agentes oxidantes. La 5-formil-2′-desoxiuridina es un compuesto potencialmente mutagénico que ha sido identificado en células expuestas a radiaciones ionizantes y a agentes oxidantes. Este compuesto se emplea para la síntesis de varios derivados de la 2′-desoxiuridina sustituidos en la posición 5. En este trabajo se presenta un método práctico para la conversión de la 2′-desoxitimidina a 3′,5′-di-O-acetil-5-formil-2′-desoxiuridina (4), a través de la halogenación, hidrólisis y oxidación de la 3′,5′-di-O-acetil-2′-desoxitimidina (1). Se realizaron estudios para seleccionar los agentes adecuados para las etapas de bromación, hidrólisis y oxidación. El bromo molecular y la N-bromosuccinimida (NBS) fueron probados en la etapa de halogenación y la NBS permitió obtener el producto deseado, 5-(bromometil)-3′,5′-di-O-acetil-2′-deoxiuridina (2) y trazas del compuesto dibromado. Algunos procedimientos de hidrólisis fueron evaluados para obtener la hidroximetil-3′,5′-di-O-acetil-2′-deoxiuridina (3) a partir de 2 y se seleccionó para esta etapa un procedimiento neutro con agua. En la etapa de oxidación, se llevó a cabo un análisis comparativo entre el óxido de manganeso activo y el reactivo de Jones para establecer las condiciones óptimas para obtener 4. Se utilizó, con buenos resultados, el reactivo de Jones para oxidar el grupo alcohol alílico, del nucleósido, a grupo formilo a través de un método más práctico, fácil y reproducible. pubtype: Academic Journal doctype: Article src: R language: English refInfo: copyright: @attributes: flag: Y custom: Copyright of Revista CENIC Ciencias Quimicas is the property of Centro Nacional de Investigaciones Cientificas and its content may not be copied or emailed to multiple sites without the copyright holder's express written permission. Additionally, content may not be used with any artificial intelligence tools or machine learning technologies. However, users may print, download, or email articles for individual use. item: Revista CENIC Ciencias Quimicas holder: Centro Nacional de Investigaciones Cientificas dt: @attributes: year: 2007 holdings: @attributes: islocal: N |
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