Synthesis of novel bicyclic nucleosides with 3,6-anhydro sugar moiety

Nucleosides, Nucleotides and Nucleic Acids

Volumn 27, Issue 10-11, 2008, Pages 1097-1106

  Kim, Myong Jung ^a,b  

^a FOUNDATION FOR APPLIED MOLECULAR EVOLUTION   (United States)

^b University of Florida ^*  (United States)

Author keywords

Antiviral agents; Bicyclic nucleoside; Intramolecular cyclization

Indexed keywords

1 (3'6' ANHYDRO 3' C HYDROXYMETHYL BETA DEXTRO GLUCOFURANOSYL) THYMINE; 6 AMINO (3'6' ANHYDRO 3' C HYDROXYMETHYL BETA DEXTRO GLUCOFURANOSYL)PURINE; ANTIVIRUS AGENT; CARBOHYDRATE DERIVATIVE; GLUCOSE DERIVATIVE; METHYL GROUP; NUCLEOSIDE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; DRUG CONFORMATION; DRUG SYNTHESIS; EPOXIDATION; HUMAN; HUMAN CELL; HUMAN IMMUNODEFICIENCY VIRUS 1; HYDROLYSIS; POLYMERIZATION; STEREOCHEMISTRY;

ANTIVIRAL AGENTS; BICYCLO COMPOUNDS; GLUCOSE; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; NUCLEOSIDES;

EID: 51649103892     PISSN: 15257770     EISSN: 15322335     Source Type: Journal    
DOI: 10.1080/15257770802341269     Document Type: Article

References (16)

1. de la Haba, G.; Cantoni, G.L. The enzymatic synthesis of S-adenosyl-L-homocysteine from adenosine and homocysteine. J. Biol. Chem. 1959, 234, 603-608.
2. Cantoni, G.L. In Biological Methylation and Drug Design, eds. R.T. Borchardt, C.R. Creveling, P.M. Ueland, Humana Press, Clifton, NJ, 1986, 227-238.
3. Montgomery, J.A.; Clayton, S.J.; Thomas, H.J.; Shannon, W.M.; Arnett, G.; Bodner, A.J.; Kion, I.-K.; Cantoni, G.L.; Chiang, P.K. Carbocyclic analog of 3-deazaadenosine: a novel antiviral agent using S-adenosylhomocysteine hydrolase as a pharmacological target. J. Med. Chem. 1982, 25, 626-629.
4. Glazer, R.I.; Hartman, K.D.; Knode, M.C.; Richard, M.M.; Chiang, P.K.; Tseng, C.K.H.; Marquez, V.E. 3-Deazaneplanocin: A new and potent inhibitor of S-adenosylhomocysteine hydrolase and its effects on human promyelocytic leukemia cell line HL-60. Biochem. Biophys. Res. Commun. 1986, 135, 688-694.
5. Kitade, Y.; Kojima, H.; Zulfiqur, F.; Kim, H.-S.; Wataya, Y. Synthesis of 2-fluoronoraristeromycin and its inhibitory activity against Plasmodium falciparum S-adenosyl-L-homocysteine hydrolase. Bioorg. Med. Chem. Lett. 2003, 13, 3963-3965.
6. Ando, T.; Iwata, M.; Zulfiqar, F.; Miyamoto, T.; Nakanishi, M.; Kitade, Y. Synthesis of 2-modified aristeromycins and their analogs as potent inhibitors against Plasmodium falciparum S-adenosyl-L-homocysteine hydrolase. Bioorg. Med. Chem. 2008, 16, 3809-3815.
7. Tanaka, N.; Nakanishi, M.; Kusakabe, Y.; Shiraiwa, K.; Yabe, S.; Ito, Y.; Kitade, Y.; Nakamura, K.T. Crystal structure of S-adenosyl-L- homocysteine hydrolase from the human malaria parasite Plasmodium falciparum. J. Mol. Biol. 2004, 343, 1007-1017.
8. Nakanishi, M.; Yabe, S.; Tanaka, N.; Ito, Y.; Nakamura, K.T.; Kitade, Y. Mutational analyses of Plasmodium falciparum and human S-adenosylhomocysteine hydrolases. Mol. Biochem. Parasitol. 2005, 143, 146-151.
9. Kitade, Y.; Kozaki, A.; Miwa, T.; Nakanishi, M. Synthesis of base-modified noraristeromycin derivatives and their inhibitory activity against human and Plasmodium falciparum recombinant S-adenosyl- Lhomocysteine hydrolase. Tetrahedron 2002, 58, 1271-1277.
10. Siddiqi, S.M.; Jacobson, K.A.; Esker, J.L.; Olah, M.E.; Ji, X.-D.; Melman, N.; Tiwari, K.N.; Secrist, J.A.; Schneller, S.W.; Cristalli, G.; Stiles, G.L.; Johnson, C.R.; Ijzerman, A.P. Search for new purine- and ribose-modified adenosine analogs as selective agonists and antagonists at adenosine receptors. J. Med. Chem. 1995, 38, 1174-1188.
11. Nair, V.; Richardson, S.G. Modification of nucleic acid bases via radical intermediates: synthesis of dihalogenated purine nucleosides. Synthesis 1982, 16, 670-672.
12. Nair, V.; Bera, B.; Kern, E.R. Synthesis and biological activities of 2-functionalized purine nucleosides. Nucleosides Nucleotides Nucleic Acid 2003, 22, 115-127.
13. Hildbrand, S.; Troxler, T.; Scheffold, R. A short synthesis of (-)-carbovir. Helvetica Chimica Acta 1994, 77, 1236-1240.
14. Poli, G. The osmylation of flexible 3-substituted cyclopentenes. Tetrahedron Lett. 1989, 30, 7385-7388.
15. Gomi, T.; Date, T.; Osawa, H.; Fujioka, M.; Aksamit, R.R.; Backlund, P.S. Jr., ; Cantoni, G.L. Expression of rat liver S-adenosylhomocysteinase cDNA in Escherichia coli and mutagenesis at the putative NAD binding site. J. Biol. Chem. 1989, 264, 16138-16142. Assay conditions: The enzyme was incubated with 100 μL adenosine, 5 mM, DL-homocysteine and inhibitors in 0.2 mL of 10 mM potassium phosphate, pH 7.2, buffer at 30°C for 2 minutes in the standard assay system. The reaction was started by the addition of 5 μL of SAHH (human: 0.43 μg, P. falciparum:0.54 μg) and terminated by the addition of 20 mL of 0.67N HCl. The reaction mixture was kept on ice until the HPLC analysis. Themixture was analyzed for SAH by a Shimadzu LC-10A VP HPLC system. In the synthetic reaction, one unit of SAH hydrolase was defined as the amount synthesizing 1 μmol of SAH/min at 30°C.
16. 3 277.1175 found 277.1170.