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Statements

Subject Item
n2:RIV%2F61388963%3A_____%2F11%3A00360664%21RIV12-AV0-61388963
rdf:type
n8:Vysledek skos:Concept
dcterms:description
Synthesis of novel nucleotide analogues 5'-deoxynucleoside-5'-S-methylphosphonates, starting from 5'-deoxy-5'-haloribonucleosides, 5'-O-tosylribonucleosides, and 2'-O-triflylnucleosides, is described. The phosphonothiolation of these compounds was achieved using S-(diisopropylphosphonomethyl) isothiouronium tosylate, a new, odourless, and efficient equivalent of mercaptomethylphosphonate. The thiolate anion of mercaptomethylphosphonate was generated in situ from the isothiouronium salt in both protic and aprotic solvents using two equivalents of sodium iso-propoxide. The prepared nucleoside 5'-S-methylphosphonates were deprotected, and the free phosphonic acids transformed into diphosphoryl derivatives (the NTP analogues). Both mononucleotides and NTP analogues were studied as substrates/inhibitors of several enzymes that are involved in the nucleoside/nucleotide metabolism. Synthesis of novel nucleotide analogues 5'-deoxynucleoside-5'-S-methylphosphonates, starting from 5'-deoxy-5'-haloribonucleosides, 5'-O-tosylribonucleosides, and 2'-O-triflylnucleosides, is described. The phosphonothiolation of these compounds was achieved using S-(diisopropylphosphonomethyl) isothiouronium tosylate, a new, odourless, and efficient equivalent of mercaptomethylphosphonate. The thiolate anion of mercaptomethylphosphonate was generated in situ from the isothiouronium salt in both protic and aprotic solvents using two equivalents of sodium iso-propoxide. The prepared nucleoside 5'-S-methylphosphonates were deprotected, and the free phosphonic acids transformed into diphosphoryl derivatives (the NTP analogues). Both mononucleotides and NTP analogues were studied as substrates/inhibitors of several enzymes that are involved in the nucleoside/nucleotide metabolism.
dcterms:title
Synthesis of novel deoxynucleoside S-methylphosphonic acids using S-(diisopropylphosphonomethyl)isothiouronium tosylate, a new equivalent of mercaptomethylphosphonate Synthesis of novel deoxynucleoside S-methylphosphonic acids using S-(diisopropylphosphonomethyl)isothiouronium tosylate, a new equivalent of mercaptomethylphosphonate
skos:prefLabel
Synthesis of novel deoxynucleoside S-methylphosphonic acids using S-(diisopropylphosphonomethyl)isothiouronium tosylate, a new equivalent of mercaptomethylphosphonate Synthesis of novel deoxynucleoside S-methylphosphonic acids using S-(diisopropylphosphonomethyl)isothiouronium tosylate, a new equivalent of mercaptomethylphosphonate
skos:notation
RIV/61388963:_____/11:00360664!RIV12-AV0-61388963
n8:predkladatel
n16:ico%3A61388963
n3:aktivita
n4:P n4:Z
n3:aktivity
P(GA202/09/0193), P(GA203/09/0820), P(KAN200520801), P(LC06061), Z(AV0Z40550506)
n3:cisloPeriodika
8
n3:dodaniDat
n10:2012
n3:domaciTvurceVysledku
n6:6236219 n6:4235010 Panova, Natalya n6:4868579
n3:druhVysledku
n7:J
n3:duvernostUdaju
n18:S
n3:entitaPredkladatele
n19:predkladatel
n3:idSjednocenehoVysledku
233910
n3:idVysledku
RIV/61388963:_____/11:00360664
n3:jazykVysledku
n12:eng
n3:klicovaSlova
phosphonate internucleotide linkage; organosulfur compounds; NTP analogues; nucleosides; nucleotides
n3:klicoveSlovo
n14:nucleotides n14:NTP%20analogues n14:phosphonate%20internucleotide%20linkage n14:organosulfur%20compounds n14:nucleosides
n3:kodStatuVydavatele
GB - Spojené království Velké Británie a Severního Irska
n3:kontrolniKodProRIV
[ED205C68734B]
n3:nazevZdroje
Organic & Biomolecular Chemistry
n3:obor
n17:CC
n3:pocetDomacichTvurcuVysledku
4
n3:pocetTvurcuVysledku
4
n3:projekt
n9:GA203%2F09%2F0820 n9:KAN200520801 n9:LC06061 n9:GA202%2F09%2F0193
n3:rokUplatneniVysledku
n10:2011
n3:svazekPeriodika
9
n3:tvurceVysledku
Buděšínský, Miloš Rosenberg, Ivan Kóšiová, Ivana Panova, Natalya
n3:wos
000288904500037
n3:zamer
n20:AV0Z40550506
s:issn
1477-0520
s:numberOfPages
5
n13:doi
10.1039/c0ob00738b