FRINK Linked Data Fragments server

Matches in SemOpenAlex for { <https://semopenalex.org/work/W2318074412> ?p ?o ?g. }

• W2318074412 endingPage "15653" @default.
• W2318074412 startingPage "15646" @default.
• W2318074412 abstract "Gemcitabine is a modified cytidine analog having two fluorine atoms at the 2'-position of the ribose ring. It has been proposed that gemcitabine inhibits RNR activity by producing a C3'• intermediate via direct H3'-atom abstraction followed by loss of HF to yield a C2'• with 3'-keto moiety. Direct detection of C3'• and C2'• during RNR inactivation by gemcitabine still remains elusive. To test the influence of 2'- substitution on radical site formation, electron spin resonance (ESR) studies are carried out on one-electron oxidized gemcitabine and other 2'-modified analogs, i.e., 2'-deoxy-2'-fluoro-2'-C-methylcytidine (MeFdC) and 2'-fluoro-2'-deoxycytidine (2'-FdC). ESR line components from two anisotropic β-2'-F-atom hyperfine couplings identify the C3'• formation in one-electron oxidized gemcitabine, but no further reaction to C2'• is found. One-electron oxidized 2'-FdC is unreactive toward C3'• or C2'• formation. In one-electron oxidized MeFdC, ESR studies show C2'• production presumably from a very unstable C3'• precursor. The experimentally observed hyperfine couplings for C2'• and C3'• match well with the theoretically predicted ones. C3'• to C2'• conversion in one-electron oxidized gemcitabine and MeFdC has theoretically been modeled by first considering the C3'• and H3O(+) formation via H3'-proton deprotonation and the subsequent C2'• formation via HF loss induced by this proximate H3O(+). Theoretical calculations show that in gemcitabine, C3'• to C2'• conversion in the presence of a proximate H3O(+) has a barrier in agreement with the experimentally observed lack of C3'• to C2'• conversion. In contrast, in MeFdC, the loss of HF from C3'• in the presence of a proximate H3O(+) is barrierless resulting in C2'• formation which agrees with the experimentally observed rapid C2'• formation." @default.
• W2318074412 created "2016-06-24" @default.
• W2318074412 creator A5001465581 @default.
• W2318074412 creator A5025405781 @default.
• W2318074412 creator A5025785039 @default.
• W2318074412 creator A5030001294 @default.
• W2318074412 creator A5041101731 @default.
• W2318074412 creator A5061668281 @default.
• W2318074412 creator A5063880477 @default.
• W2318074412 date "2014-10-23" @default.
• W2318074412 modified "2023-10-14" @default.
• W2318074412 title "One-Electron Oxidation of Gemcitabine and Analogs: Mechanism of Formation of C3′ and C2′ Sugar Radicals" @default.
• W2318074412 cites W1510914671 @default.
• W2318074412 cites W1931508686 @default.
• W2318074412 cites W1969023429 @default.
• W2318074412 cites W1972972944 @default.
• W2318074412 cites W1973159565 @default.
• W2318074412 cites W1974323152 @default.
• W2318074412 cites W1981912201 @default.
• W2318074412 cites W1984759551 @default.
• W2318074412 cites W1985181588 @default.
• W2318074412 cites W1988709046 @default.
• W2318074412 cites W1992099027 @default.
• W2318074412 cites W1996507998 @default.
• W2318074412 cites W1997151511 @default.
• W2318074412 cites W1999537037 @default.
• W2318074412 cites W2000798385 @default.
• W2318074412 cites W2001008810 @default.
• W2318074412 cites W2001584279 @default.
• W2318074412 cites W2003298794 @default.
• W2318074412 cites W2005783000 @default.
• W2318074412 cites W2012512658 @default.
• W2318074412 cites W2012730317 @default.
• W2318074412 cites W2013359823 @default.
• W2318074412 cites W2016344675 @default.
• W2318074412 cites W2017261079 @default.
• W2318074412 cites W2026122224 @default.
• W2318074412 cites W2026946054 @default.
• W2318074412 cites W2028371684 @default.
• W2318074412 cites W2031152582 @default.
• W2318074412 cites W2035833707 @default.
• W2318074412 cites W2045180549 @default.
• W2318074412 cites W2049465538 @default.
• W2318074412 cites W2054988125 @default.
• W2318074412 cites W2066285015 @default.
• W2318074412 cites W2068485994 @default.
• W2318074412 cites W2073886057 @default.
• W2318074412 cites W2083112495 @default.
• W2318074412 cites W2084743201 @default.
• W2318074412 cites W2087193480 @default.
• W2318074412 cites W2090684905 @default.
• W2318074412 cites W2103189978 @default.
• W2318074412 cites W2129811654 @default.
• W2318074412 cites W2133478112 @default.
• W2318074412 cites W2134773678 @default.
• W2318074412 cites W2161632777 @default.
• W2318074412 cites W2165480504 @default.
• W2318074412 cites W2313576982 @default.
• W2318074412 cites W2318222393 @default.
• W2318074412 cites W2319775556 @default.
• W2318074412 cites W2319911380 @default.
• W2318074412 cites W2505074369 @default.
• W2318074412 cites W2079241564 @default.
• W2318074412 doi "https://doi.org/10.1021/ja5083156" @default.
• W2318074412 hasPubMedCentralId "https://www.ncbi.nlm.nih.gov/pmc/articles/4227712" @default.
• W2318074412 hasPubMedId "https://pubmed.ncbi.nlm.nih.gov/25296262" @default.
• W2318074412 hasPublicationYear "2014" @default.
• W2318074412 type Work @default.
• W2318074412 sameAs 2318074412 @default.
• W2318074412 citedByCount "13" @default.
• W2318074412 countsByYear W23180744122015 @default.
• W2318074412 countsByYear W23180744122016 @default.
• W2318074412 countsByYear W23180744122017 @default.
• W2318074412 countsByYear W23180744122018 @default.
• W2318074412 countsByYear W23180744122019 @default.
• W2318074412 countsByYear W23180744122020 @default.
• W2318074412 countsByYear W23180744122022 @default.
• W2318074412 crossrefType "journal-article" @default.
• W2318074412 hasAuthorship W2318074412A5001465581 @default.
• W2318074412 hasAuthorship W2318074412A5025405781 @default.
• W2318074412 hasAuthorship W2318074412A5025785039 @default.
• W2318074412 hasAuthorship W2318074412A5030001294 @default.
• W2318074412 hasAuthorship W2318074412A5041101731 @default.
• W2318074412 hasAuthorship W2318074412A5061668281 @default.
• W2318074412 hasAuthorship W2318074412A5063880477 @default.
• W2318074412 hasBestOaLocation W23180744121 @default.
• W2318074412 hasConcept C121332964 @default.
• W2318074412 hasConcept C131538251 @default.
• W2318074412 hasConcept C134121241 @default.
• W2318074412 hasConcept C139066938 @default.
• W2318074412 hasConcept C141071460 @default.
• W2318074412 hasConcept C178790620 @default.
• W2318074412 hasConcept C184779094 @default.
• W2318074412 hasConcept C185592680 @default.
• W2318074412 hasConcept C187961010 @default.
• W2318074412 hasConcept C191897082 @default.
• W2318074412 hasConcept C192562407 @default.
• W2318074412 hasConcept C2776694085 @default.

• next