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Synthesis of novel deoxynucleoside S-methylphosphonic acids using S-(diisopropylphosphonomethyl)isothiouronium tosylate, a new equivalent of mercaptomethylphosphonate

SYSNO ASEP	0360664
Document Type	J - Journal Article
R&D Document Type	Journal Article
Subsidiary J	Článek ve WOS
Title	Synthesis of novel deoxynucleoside S-methylphosphonic acids using S-(diisopropylphosphonomethyl)isothiouronium tosylate, a new equivalent of mercaptomethylphosphonate
Author(s)	Markusová Kóšiová, Ivana (UOCHB-X)_{RID, ORCID} Buděšínský, Miloš (UOCHB-X)_{RID, ORCID} Panova, Natalya (UOCHB-X)_RID Rosenberg, Ivan (UOCHB-X)_{RID, ORCID}
Number of authors	4
Source Title	Organic & Biomolecular Chemistry. - : Royal Society of Chemistry - ISSN 1477-0520 Roč. 9, č. 8 (2011), s. 2856-2860
Number of pages	5 s.
Language	eng - English
Country	GB - United Kingdom
Keywords	phosphonate internucleotide linkage ; organosulfur compounds ; NTP analogues ; nucleosides ; nucleotides
Subject RIV	CC - Organic Chemistry
R&D Projects	KAN200520801 GA AV ČR - Academy of Sciences of the Czech Republic (AV ČR)
	GA202/09/0193 GA ČR - Czech Science Foundation (CSF)
	GA203/09/0820 GA ČR - Czech Science Foundation (CSF)
	LC06061 GA MŠMT - Ministry of Education, Youth and Sports (MEYS)
CEZ	AV0Z40550506 - UOCHB-X (2005-2011)
UT WOS	000288904500037
DOI	10.1039/c0ob00738b
Annotation	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.
Workplace	Institute of Organic Chemistry and Biochemistry
Contact	asep@uochb.cas.cz ; Kateřina Šperková, Tel.: 232 002 584 ; Viktorie Chládková, Tel.: 232 002 434
Year of Publishing	2012

Number of the records: 1