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

Content Provider	Royal Society of Chemistry (RSC)
Author	Panova, Natalya Kóšiová, Ivana Buděšínský, Miloš Rosenberg, Ivan
Copyright Year	2011
Abstract	The synthesis of the 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 were 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.
Starting Page	2856
Ending Page	2860
Page Count	5
File Format	HTM / HTML PDF
ISSN	14770520
Volume Number	9
Issue Number	8
Journal	Organic & Biomolecular Chemistry
DOI	10.1039/c0ob00738b
Language	English
Publisher	Royal Society of Chemistry
Access Restriction	Open
Subject Keyword	Sodium Nucleotide Tosyl Ion Nucleoside Nucleoside triphosphate NTP Isothiouronium Metabolism
Content Type	Text
Resource Type	Article
Subject	Organic Chemistry Biochemistry Physical and Theoretical Chemistry

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