About: Gas-phase tautomers of protonated 1-methylcytosine. Preparation, energetics, and dissociation mechanisms     Goto   Sponge   NotDistinct   Permalink

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  • Tautomers of 1-methylcytosine that are protonated at N-3(1+) and C-5(2+) have been specifically synthesized in the gas phase and characterized by tandem mass spectrometry and quantum chemical calculation. Ion 1+ is the most stable tautomer in aqueous and methanol solution and is likely to be formed by electrospray ionization of 1-methylcytosine and transferred in the gas phase. Gas-phase protonation of 1-methylcytosine produces a mixture of 1+ and the O-2-protonated tautomer (3+), which are nearly isoenergetic. Dissociative ionization of 6-ethyl-5,6-dihydro-1-methylcytosine selectively forms isomer 2+. Upon collisional activation, ions 1+ and 3+ dissociate by loss of ammonia and [C,H,N,O], whose mechanis,s have been established by deuterium labeling and ab initio calculations. The main dissociations of 2+ following collisional activation are losses CH2=C=NH and HN=C=O.
  • Tautomers of 1-methylcytosine that are protonated at N-3(1+) and C-5(2+) have been specifically synthesized in the gas phase and characterized by tandem mass spectrometry and quantum chemical calculation. Ion 1+ is the most stable tautomer in aqueous and methanol solution and is likely to be formed by electrospray ionization of 1-methylcytosine and transferred in the gas phase. Gas-phase protonation of 1-methylcytosine produces a mixture of 1+ and the O-2-protonated tautomer (3+), which are nearly isoenergetic. Dissociative ionization of 6-ethyl-5,6-dihydro-1-methylcytosine selectively forms isomer 2+. Upon collisional activation, ions 1+ and 3+ dissociate by loss of ammonia and [C,H,N,O], whose mechanis,s have been established by deuterium labeling and ab initio calculations. The main dissociations of 2+ following collisional activation are losses CH2=C=NH and HN=C=O. (en)
  • Tautomery 1-methylcytosinu protonovaného v poloze N-3 (1+•) a C-5 (2+•) byly specificky připraveny v plynné fázi a charakterizovány pomocí tandemové hmotnostní spektrometrie a kvantově chemických výpočtů. Ion 1+• je nejstabilnějším tautomerem ve vodném a methanolickém roztoku a je tvořen při ionizaci 1-methylcytosinu elektrosprejem. Protonací 1-methylcytosinu v plynné fázi vzniká směs 1+• a O-2 protonovaného tautomeru (3+•), které jsou téměř isoenergetické. Disociativní ionizace 6-ethyl-5,6-dihydro-1-methylcytosinu poskytuje selektivně isomer 2+•. Při kolizní aktivaci ionty 1+• a 2+• disociují ztrátami amoniaku a [C,H,N,O], jejichž mechanizmy byly studovány pomocí izotopického značení deuteriem a ab initio výpočtů. Hlavními disociacemi kolizně aktivovaných iontů 2+• jsou ztráty CH2=C=NH a HN=C=O. Mechanizmy těchto reakcí byly objasněny izotopickým značením a teoretickými výpočty. (cs)
Title
  • Gas-phase tautomers of protonated 1-methylcytosine. Preparation, energetics, and dissociation mechanisms
  • Tautomery protonovaného 1-methylcytosinu v plynné fázi. Příprava, energetika a disociační mechanizmy (cs)
  • Gas-phase tautomers of protonated 1-methylcytosine. Preparation, energetics, and dissociation mechanisms (en)
skos:prefLabel
  • Gas-phase tautomers of protonated 1-methylcytosine. Preparation, energetics, and dissociation mechanisms
  • Tautomery protonovaného 1-methylcytosinu v plynné fázi. Příprava, energetika a disociační mechanizmy (cs)
  • Gas-phase tautomers of protonated 1-methylcytosine. Preparation, energetics, and dissociation mechanisms (en)
skos:notation
  • RIV/61388955:_____/05:00023555!RIV06-AV0-61388955
http://linked.open.../vavai/riv/strany
  • 1417;1428
http://linked.open...avai/riv/aktivita
http://linked.open...avai/riv/aktivity
  • P(GA203/02/0737), P(IAA400400502), Z(AV0Z40400503)
http://linked.open...iv/cisloPeriodika
  • 11
http://linked.open...vai/riv/dodaniDat
http://linked.open...aciTvurceVysledku
http://linked.open.../riv/druhVysledku
http://linked.open...iv/duvernostUdaju
http://linked.open...titaPredkladatele
http://linked.open...dnocenehoVysledku
  • 522421
http://linked.open...ai/riv/idVysledku
  • RIV/61388955:_____/05:00023555
http://linked.open...riv/jazykVysledku
http://linked.open.../riv/klicovaSlova
  • nucleobases; cytosine; tandem mass spectrometry; ab initio calculations (en)
http://linked.open.../riv/klicoveSlovo
http://linked.open...odStatuVydavatele
  • GB - Spojené království Velké Británie a Severního Irska
http://linked.open...ontrolniKodProRIV
  • [2F88939A33A5]
http://linked.open...i/riv/nazevZdroje
  • Journal of Mass Spectrometry
http://linked.open...in/vavai/riv/obor
http://linked.open...ichTvurcuVysledku
http://linked.open...cetTvurcuVysledku
http://linked.open...vavai/riv/projekt
http://linked.open...UplatneniVysledku
http://linked.open...v/svazekPeriodika
  • 40
http://linked.open...iv/tvurceVysledku
  • Polášek, Miroslav
  • Tureček, F.
  • Cuadrado-Peinado, M. L.
  • Yao, Ch.
http://linked.open...n/vavai/riv/zamer
issn
  • 1076-5174
number of pages
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