A convenient and efficient synthesis of a novel class of acyclic nucleoside phosphonates derived from 2-(phosphonomethoxy)propanoic acid has been developed. The key step of the synthesis is the optimized oxidation of the 3-hydroxy-2-(phosphonomethoxy)propyl (HPMP) analogues to the corresponding 2'-carboxy-PME (CPME) derivatives using the TEMPO/NaClO2/NaClO oxidizing system. Although (S)-3-(adenin-9-yl)-2-(phosphonomethoxy)propanoic acid ((S)-CPMEA) has been designed as a compound with potential anti-HIV activity, none of the newly prepared CPME analogues exhibited any antiviral activity.

Institute of Organic Chemistry and Biochemistry Academy of Sciences of the Czech Republic v v i Flemingovo nám 2 CZ 16610 Prague 6 Czech Republic

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De Clercq E., Holý A., Rosenberg I., Sakuma T., Balzarini J., Maudgal P.C. Nature. 1986;323:464. PubMed

De Clercq E. J. Med. Microbiol. 1998;47:1. PubMed

Holý A. Curr. Pharm. Des. 2003;9:2567. PubMed

De Clercq E., Holý A. Nat. Rev. Drug Discov. 2005;4:928. PubMed

Holý A. Antiviral Res. 2006;71:248. PubMed

De Clercq E. Antiviral Res. 2007;75:1. PubMed

De Clercq E. Biochem. Pharmacol. 2007;73:911. PubMed

Holý A., Votruba I., Tloušťová E., Masojídková M. Collect. Czech. Chem. Commun. 2001;66:1545.

Zídek Z., Potměšil P., Holý A. Toxicol. Appl. Pharmacol. 2003;192:246. PubMed

Reiser H., Wang J., Chong L., Watkins W.J., Ray A.S., Shibata R., Birkus G., Cihlar T., Wu S., Li B., Liu X., Henne I.N., Wolfgang G.H.I., Desai M., Rhodes G.R., Fridland A., Lee W.A., Plunkett W., Vail D., Thamm D.H., Jeraj R., Tumas D.B. Clin. Cancer. Res. 2008;14:2824. PubMed

Keough D.T., Hocková D., Holý A., Naesens L.M.J., Skinner-Adams T.S., de Jersey J., Guddat L.W. J. Med. Chem. 2009;52:4391. PubMed

Hocková D., Holý A., Masojídková M., Keough D.T., de Jersey J., Guddat L.W. Bioorg. Med. Chem. 2009;17:6218. PubMed

Zídek Z., Franková D., Holý A. Int. J. Immunopharmacol. 2000;22:1121. PubMed

Zídek Z., Potměšil P., Kmoníčková E., Holý A. Eur. J. Pharmacol. 2003;475:149. PubMed

Potměšil P., Krečmerová M., Kmoníčková E., Holý A., Zídek Z. Eur. J. Pharmacol. 2006;540:191. PubMed

De Clercq E. Intervirology. 1997;40:295. PubMed

De Clercq E. Clin. Microbiol. Rev. 2003;16:569. PubMed PMC

De Clercq E. Expert Rev. Anti-infect. Ther. 2003;1:21. PubMed

De Clercq E., Holý A. Antimicrob. Agents Chemother. 1991;35:701. PubMed PMC

Neyts J., Snoeck R., Balzarini J., De Clercq E. Antiviral Res. 1991;16:41. PubMed

De Clercq E. Rev. Med. Virol. 1993;3:85.

Hitchcock M.J.M., Jaffe H.S., Martin J.C., Stagg R.J. Antiviral Chem. Chemother. 1996;7:115.

Holý A., Votruba I., Masojídková M., Andrei G., Snoeck R., Naesens L., De Clercq E., Balzarini J. J. Med. Chem. 2002;45:1918. PubMed

Balzarini J., Pannecouque C., De Clercq E., Aquaro S., Perno C.-F., Egberink H., Holý A. Antimicrob. Agents Chemother. 2002;46:2185. PubMed PMC

Hocková D., Holý A., Masojídková M., Andrei G., Snoeck R., De Clercq E., Balzarini J. J. Med. Chem. 2003;46:5064. PubMed

Hocková D., Holý A., Masojídková M., Andrei G., Snoeck R., De Clercq E., Balzarini J. Bioorg. Med. Chem. 2004;12:3197. PubMed

Ying C., Holý A., Hocková D., Havlas Z., De Clercq E., Neyts J. Antimicrob. Agents Chemother. 2005;49:1177. PubMed PMC

Wagner C.R., Iyer V.V., McIntee E.J. Med. Res. Rev. 2000;20:417. PubMed

Hecker S.J., Erion M.D. J. Med. Chem. 2008;51:2328. PubMed

Holý A., Rosenberg I. Collect. Czech. Chem. Commun. 1987;52:2775.

Rosenberg I., Holý A. Collect. Czech. Chem. Commun. 1987;52:2792.

Krečmerová M., Masojídková M., Holý A. Collect. Czech. Chem. Commun. 2004;69:1889.

Janeba Z., Masojídková M., Holý A. Collect. Czech. Chem. Commun. 2010;75:371.

Jindřich J., Holý A., Dvořáková H. Collect. Czech. Chem. Commun. 1993;58:1645.

Balzarini J., Holý A., Jindřich J., Dvořáková H., Hao Z., Snoeck R., Herdewijn P., John D.G., De Clercq E. Proc. Natl. Acad. Sci. U.S.A. 1991;88:4961. PubMed PMC

Balzarini J., Holý A., Jindřich J., Naesens L., Snoeck R., Schols D., De Clercq E. Antimicrob. Agents Chemother. 1993;37:332. PubMed PMC

De Clercq E., Descamps J., De Somer P., Holý A. Science. 1978;200:563. PubMed

De Clercq E., Holý A. J. Med. Chem. 1979;22:510. PubMed

Holý A., Votruba I., De Clercq E. Collect. Czech. Chem. Commun. 1982;47:1392.

Holý A., Votruba I., De Clercq E. Collect. Czech. Chem. Commun. 1985;50:262.

De Clercq E., Holý A. J. Med. Chem. 1985;28:282. PubMed

De Clercq E. Nucleosides Nucleotides Nucleic Acids. 2005;24:1395. PubMed

Votruba I., Hasobe M., Holý A., Borchardt R.T. Biochem. Pharmacol. 1990;39:1573. PubMed

Tuske S., Sarafianos S.G., Clark A.D., Jr., Ding J., Naeger L.K., White K.L., Miller M.D., Gibbs C.S., Boyer P.L., Clark P., Wang G., Gaffney B.L., Jones R.A., Jerina D.M., Hughes S.H., Arnold E. Nat. Struct. Mol. Biol. 2004;11:469. PubMed

Webb R.R., Martin J.C. Tetrahedron Lett. 1987;28:4963.

Holý A. Collect. Czech. Chem. Commun. 1993;58:649.

Bäckvall J.-E., editor. Modern Oxidation Methods. WILEY-VCH; Weinheim: 2004.

Hutchison A.J., Williams M., De Jesus R., Yokoyama R., Oei H.H., Ghai G.R., Webb R.L., Zoganas H.C., Stone G.A., Jarvis M.F. J. Med. Chem. 1990;33:1919. PubMed

Ha S.B., Nair V. Tetrahedron Lett. 1996;37:1567.

Mori N., Togo H. Tetrahedron. 2005;61:5915.

Singh A.K., Varma R.S. Tetrahedron Lett. 1992;33:2307.

Varma R.S., Hogan M.E. Tetrahedron Lett. 1992;33:7719.

Homma H., Watanabe Y., Abiru T., Murayama T., Nomura Y., Matsuda A. J. Med. Chem. 1992;35:2881. PubMed

Vogler T., Studer A. Synthesis. 2008:1979.

De Souza M.V.N. Mini-Rev. Org. Chem. 2006;3:155.

Nooy A.E.J., Besemer A.C., Van Bekkum H. Synthesis. 1996:1153.

De Mico A., Margarita R., Parlanti L., Vescovi A., Piancatelli G. J. Org. Chem. 1997;62:6974.

Epp J.B., Widlanski T.S. J. Org. Chem. 1999;64:293. PubMed

Zhao M., Li J., Mano E., Song Z., Tschaen D.M., Grabowski E.J.J., Reider P.J. J. Org. Chem. 1999;64:2564.

Holý A., Rosenberg I. Collect. Czech. Chem. Commun. 1982;47:3447.

Jansa P., Holý A., Dračínský M., Baszczyňski O., Česnek M., Janeba Z. Collect. Symp. Ser. 2011;12:347.

Jansa, P.; et al., Green. Chem., in press.

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Regioselective Palmitoylation of 9-(2,3-Dihydroxy- propyl)adenine Catalyzed by a Glycopolymer-enzyme Conjugate