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| Campo DC | Valor | Lengua/Idioma |
|---|---|---|
| dc.creator | Sun, Huabing | - |
| dc.creator | Taverna Porro, Marisa Lia | - |
| dc.creator | Greenberg, Marc M. | - |
| dc.date | 2018-06-06T20:32:58Z | - |
| dc.date | 2018-06-06T20:32:58Z | - |
| dc.date | 2017-10 | - |
| dc.date | 2018-06-06T19:44:14Z | - |
| dc.date.accessioned | 2019-04-29T15:52:53Z | - |
| dc.date.available | 2019-04-29T15:52:53Z | - |
| dc.date.issued | 2017-10 | - |
| dc.identifier | Sun, Huabing; Taverna Porro, Marisa Lia; Greenberg, Marc M.; Independent Generation and Reactivity of Thymidine Radical Cations; American Chemical Society; Journal of Organic Chemistry; 82; 20; 10-2017; 11072-11083 | - |
| dc.identifier | 0022-3263 | - |
| dc.identifier | http://hdl.handle.net/11336/47605 | - |
| dc.identifier | CONICET Digital | - |
| dc.identifier | CONICET | - |
| dc.identifier.uri | http://rodna.bn.gov.ar:8080/jspui/handle/bnmm/304494 | - |
| dc.description | Thymidine radical cation (1) is produced by ionizing radiation and has been invoked as an intermediate in electron transfer in DNA. Previous studies on its structure and reactivity have utilized thymidine as a precursor, which limits quantitative product analysis because thymidine is readily reformed from 1. In this investigation, radical cation 1 is independently generated via β-heterolysis of a pyrimidine radical generated photochemically from an aryl sulfide. Thymidine is the major product (33%) from 1 at pH 7.2. Diastereomeric mixtures of thymidine glycol and the corresponding 5-hydroxperoxides resulting from water trapping of 1 are formed. Significantly lower yields of products such as 5-formyl-2′-deoxyuridine that are ascribable to deprotonation from the C5-methyl group of 1 are observed. Independent generation of the N3-methyl analogue of 1 (NMe-1) produces considerably higher yields of products derived from water trapping, and these products are formed in much higher yields than those attributable to the C5-methyl group deprotonation in NMe-1. N3-Methyl-thymidine is, however, the major product and is produced in as high as 70% yield when the radical cation is produced in the presence of excess thiol. The effects of exogenous reagents on product distributions are consistent with the formation of diffusively free radical cations (1, NMe-1). This method should be compatible with producing radical cations at defined positions within DNA. | - |
| dc.description | Fil: Sun, Huabing. University Johns Hopkins; Estados Unidos | - |
| dc.description | Fil: Taverna Porro, Marisa Lia. University Johns Hopkins; Estados Unidos. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina | - |
| dc.description | Fil: Greenberg, Marc M.. University Johns Hopkins; Estados Unidos | - |
| dc.format | application/pdf | - |
| dc.format | application/pdf | - |
| dc.language | eng | - |
| dc.publisher | American Chemical Society | - |
| dc.relation | info:eu-repo/semantics/altIdentifier/doi/https://dx.doi.org/10.1021/acs.joc.7b02017 | - |
| dc.relation | info:eu-repo/semantics/altIdentifier/url/https://pubs.acs.org/doi/10.1021/acs.joc.7b02017 | - |
| dc.rights | info:eu-repo/semantics/restrictedAccess | - |
| dc.rights | https://creativecommons.org/licenses/by-nc-sa/2.5/ar/ | - |
| dc.source | reponame:CONICET Digital (CONICET) | - |
| dc.source | instname:Consejo Nacional de Investigaciones Científicas y Técnicas | - |
| dc.source | instacron:CONICET | - |
| dc.subject | RADICAL CATION | - |
| dc.subject | DNA LESIONS | - |
| dc.subject | IRRADIATION | - |
| dc.subject | Otras Ciencias Químicas | - |
| dc.subject | Ciencias Químicas | - |
| dc.subject | CIENCIAS NATURALES Y EXACTAS | - |
| dc.title | Independent Generation and Reactivity of Thymidine Radical Cations | - |
| dc.type | info:eu-repo/semantics/article | - |
| dc.type | info:eu-repo/semantics/publishedVersion | - |
| dc.type | info:ar-repo/semantics/articulo | - |
| Aparece en las colecciones: | CONICET | |
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