Recent advances in L-nucleosides: Chemistry and biology

Antiviral Research

Volumn 40, Issue 1-2, 1998, Pages 19-44

  Wang, Peiyuan ^a   Hong, Joon H ^a   Cooperwood, John S ^a   Chu, Chung K ^a  

^a UNIVERSITY OF GEORGIA   (United States)

Author keywords

Biologial activities; L Nucleoside analogs; Mode of action

Indexed keywords

1,3 OXATHIOLANE DERIVATIVE; ANTI HUMAN IMMUNODEFICIENCY VIRUS AGENT; ANTIVIRUS AGENT; CARBOVIR; CYTARABINE; LAMIVUDINE; NUCLEOSIDE; ZIDOVUDINE;

ANTIVIRAL ACTIVITY; CONTROLLED STUDY; DRUG MECHANISM; DRUG STRUCTURE; DRUG SYNTHESIS; ENANTIOMER; NONHUMAN; PRIORITY JOURNAL; REVIEW;

ANIMALS; HUMANS; MOLECULAR STRUCTURE; NUCLEOSIDES;

EID: 0032403491     PISSN: 01663542     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0166-3542(98)00041-2     Document Type: Review

References (120)

1. Acton E.M., Ryan K.J., Goodman L. Synthesis of L-ribofuranose and L-adenosine. J. Chem. Soc. 86:1964;5352-5354.
2. Ashley G.W. Modelling synthesis and hybridization properties of L-ribonucleic acid. J. Am. Chem. Soc. 114:1992;9731-9736.
3. Balzarini J., Baumgartner H., Bodenteich M., De Clercq E., Griengl H. Synthesis and antiviral activity of the enantiomeric forms of carba-5-iodo-2′-deoxyuridine and carba-(E)-5-(2-bromovinyl)-2′-deoxyuridine. J. Med. Chem. 32:1989;1861-1865.
4. Bartlett J.A., Benoit S.L., Johnson V.A.et al. Lamivudine plus Zidovudine compared with Zalcitabine plus Zidovudine in patients with HIV infection. Ann. Intern. Med. 125:1996;161-172.
5. Beach J.W., Jeong L.S., Alves A.J.et al. Synthesis of enantiomerically pure 2′R,5′S(-)-[2-(hydroxymethyl)oxathiola-5-yl]-cytosine as a potent antiviral agent against hepatitis B virus (HBV) and human immunodeficiency virus (HIV). J. Org. Chem. 57:1992;2217-2219.
6. Belleau, B., Dixit, D., Nguyen-Bu, N., Kraus, J.-L., 1989a. International Conference on AIDS. Montreal, Canada, 4-9 June, paper no T.C.O.1.
7. Belleau, B., Dixit, D., Nguyen-Bu, N., 1989b. Eur. Patent Appl., 337713.
8. Bennett L.E., Parker W.B., Allan P.W.et al. Phosphorylation of the enantiomers of the carbocyclic analog of 2′-deoxyguanosine in cells infected with herpes simplex virus type 1 and in uninfected cells. Lack of enantiomeric selectivity with viral thymidine kinase. Mol. Pharmacol. 44:1993;1258-1266.
9. Birnbaun G.I., Giziewicz J., Gabe E.J., Lin T.-S., Prusoff W.H. Structure and conformation of 3′-azido-3′-deoxythymidine (AZT), an inhibitor of the HIV (AIDS) virus. Can. J. Chem. 65:1987;2135-2139.
10. Bolon P.J., Wang P.Y., Chu C.K.et al. Anti-human immunodeficiency and anti-hepatitis B virus activities of β-L-2′,3′-dideoxy purine nucleosides. Bioorg. Med. Chem. Lett. 6:1996;1657-1662.
11. Boucher C.A., Cammack N., Schipper P.et al. High-level resistance to (-)-enantiomeric 2′-deoxy-3′-thiacytidine in vitro is due to one amino acid substitution in the catalytic site of human immonodeficiency virus type 1 reverse transcriptase. Antimicrob. Agents Chemother. 37:1993;2231-2234.
12. Cammack N.C., Rouse P.L., Marr C.L.P.et al. Cellular metabolism of (-)-enantiomeric 2′-deoxy-3′-thiacytidine. Biochem. Pharmacol. 43:1992;2059-2064.
13. Chang C.-N., Doong S.-L., Zhou J.H.et al. Deoxycytidine deamination-resistant stereoisomer is the active form of (-)-2′,3′-dideoxy-3′-thiacytidine in the inhibition of hepatitis B virus replication. J. Biol. Chem. 267:1992;13938-13942.
14. Choi W.B., Wilson L.J., Yeola S., Liotta D.C. In situ complexation directs the stereochemistry of N-glycosylation in the synthesis of oxathiolanyl and dioxolanyl nucleoside analogues. J. Am. Chem. Soc. 113:1991;9377-9379.
15. Choi, Y., Lee, K., Hong, J.H., Schinazi, R.F., Chu, C.K., 1998. Synthesis and anti-HIV activity of L-2′-fluoro-2′,3′-unsaturated purine nucleosides. Tetrahedron Lett. 4437-4444.
16. Chu C.K., Beach J.W., Jeong L.S.et al. Enantiomeric synthesis of (+)-BCH-189 [(+)-(2S,5R)-1-[2-(hydroxymethyl)-1,3-oxathiolan-5-yl]-cytosine] from D-mannose and its anti-HIV activity. J. Org. Chem. 56:1991;6503-6505.
17. Chu C.K., Ahn S.K., Kim H.O.et al. Asymmetric synthesis of enantiomerically pure (-)-(1′R,4′R)-dioxolane-thymine and its anti-HIV activity. Tetrahedron Lett. 32:1991;3791-3794.
18. Chu C.K., Schinazi R.F., Arnold B.H.et al. Comparative activity of 2′,3′-saturated and unsaturated pyrimidine and purine nucleosides against human immunodeficiency virus type 1 in peripheral blood mononuclear cells. Biochem. Pharmacol. 37:1988;3543-3548.
19. Chu C.K., Ma T.W., Shanmuganathan K.et al. Use of 2′-fluoro-5-methyl-β-L-arabinofuranosyluracil as a novel antiviral agent for hepatitis B virus and Epstein-Barr virus. Antimicrob. Agents Chemother. 39:1995;979-981.
20. Coates J.A.V., Cammack N., Jenkinson H.J.et al. The separated enantiomers of 2′-deoxy-3′-thiacytidine (BCH-189) both inhibit human immunodeficiency virus replication in vitro. Antimicrob. Agents Chemother. 36:1992;202-205.
21. Coates J.A.V., Inggall H.J., Pearson B.A.et al. Carbovir: the (-) enantiomer is a potent and selective antiviral agent against human immunodeficiency virus in vitro. Antiviral Res. 15:1991;161-168.
22. Cui L., Schinazi R.F., Gosselin G., Imbach J.-L., Chu C.K., Rando R.F., Revankar G.R., Sommadossi J.-P. Effect of β-enantiomeric and racemic nucleoside analogues on mitochondrial function in HepG2 cells: implication for predicting drug hepatotoxicity. Biochem. Pharmacol. 52:1996;1577-1584.
23. Dienstag J.L., Perrillo R.P., Schiff E.R., Bartholomev M., Vicary C., Rubin M. A preliminary trial of lamivudine for chronic hepatitis B infection. New Engl. J. Med. 333:1995;1657-1661.
24. Doong S.-L., Tsai C.H., Schinazi R.F., Liotta D.C., Cheng Y.-C. Inhibition of the replication of hepatitis B virus in vitro by 2′-deoxy-3′-thiacytidine and related analogues. Proc. Natl. Acad. Sci. USA. 88:1991;8495-8499.
25. Du, J., Choi, Y., Lee, K., Chun, B.K., Hong, J.H., Chu, C.K., 1998. A practical syntheses of L-FMAU from L-arbinose. Nucleosides Nucleotides, in press.
26. + cells per cubic millimeter. New Engl. J. Med. 333:1995;1662-1669.
27. Faraj A., Agrofoglio L.A., Wakefield J.K.et al. Inhibition of human immunodeficiency virus type 1 reverse transcriptase by the 5′-triphosphate β-enantiomers of cytidine analogues. Antimicrob. Agents Chemother. 38:1994;2300-2305.
28. Focher F., Maga G., Bendiscioli A.et al. Stereospecificity of human DNA polymersae α, β, γ, δ and ε, HIV-reverse transcriptase, HSV-1 DNA polymerase, calf thymus terminal transferase and Escherichia coli DNA polymerase I in recognizing D- and L-thymidine-5′-triphosphate as substrate. Nucleic Acids Res. 23:1995;2840-2847.
29. Fourel I., Cullen J., Saputelli J.et al. Evidence that hepatocyte turnover is required for rapid clearance of duck hepatitis B virus during antiviral therapy of chronically infected ducks. J. Virol. 68:1994;8321-8330.
30. Fourel I., Hantz O., Watanabe K.A.et al. Inhibitory effects of 2′-fluoro arabinosyl-pyrimidine nucleosides on woodchuck hepatitis virus replication in chronically infected woodchucks. Antimicrob. Agents Chemother. 34:1990;473-475.
31. Fourel I., Li J., Hantz O., Jacquet C., Fox J.J., Trépo C. Effects of 2′-fluorinated arabinosyl-pyrimidine nucleosides on duck hepatitis B virus DNA level in serum and liver of chronically infected ducks. J. Med. Virol. 37:1992;122-126.
32. Frick L.W., Lambe C.U., St. John L., Taylor L.C., Nelson D.J. Pharmacokinetics, oral bioavailability, and metabolism in mice and cynomolgus monkeys of (2″R,5″S)-cis-5-fluoro-1-[2-(hydroxymethyl)oxathiolan-5-yl]-cytosine , as agent active against human immunodeficiency virus and hepatitis B virus. Antimicrob. Agents Chemother. 38:1994;2722-2729.
33. Fujimori S., Iwanami N., Hashimoto Y., Shudo K. A convenient and stereoselective synthesis of 2′-deoxy-β-L-ribonucleosides. Nucleosides Nucleotides. 11:1992;341-349.
34. Furman P.A., Wilson J.E., Reardon J.E., Painter G.R. The effect of absolute configuration on the anti-HIV and anti-HBV activity of nucleoside analogues. Antiviral Chem. Chemother. 6:1995;345-355.
35. Furman P.A., Davis M., Liotta D.C.et al. The anti-hepatitis B virus activities, cytotoxicities, and anabolic profiles of the (-) and (+) enantiomers of cis-5-fluoro-1-[2-(hydroxymethyl)-1,3-oxathiolan-5-yl]-cytosine. Antimicrob. Agents Chemother. 36:1992;2686-2692.
36. Garbesi A., Capobianco M.L., Colonna F.P.et al. L-DNAs as potential anti-messenger oliogonucleotides: a reassessment. Nucleic Acids Res. 21:1993;4159-4164.
37. Gosselin G., Schinazi R.F., Sommadossi J.-P.et al. Anti-human immunodeficiency virus activities of the β-L-enantiomer of 2′,3′-dideoxycytidine and its 5-fluoro derivative in vitro. Antimicrob. Agents Chemother. 38:1994;1292-1297.
38. Grove K.L., Guo X., Liu S.-H., Kukhanova M., Chu C.K., Cheng C.-Y. Beta-L-(-)-dioxolane cytidine (β-L-OddC) as a potent compound for the treatment of cancer. Nucleosides Nucleotides. 16:1997;1229-1233.
39. Grove K.L., Guo X., Liu S.-H., Gao Z., Chu C.K., Cheng Y.-C. Anticancer activity of β-L-dioxolane-cytidine, a novel nucleoside analogue with the unnatural L configuration. Cancer Res. 55:1995;3008-3011.
40. Gulick R.M., Mellors J.W., Havlir D.et al. Treatment, with indinavir, zidovudine, and, lamivudine in adults with human immunodeficiency virus infection and prior antiretroviral therapy. New Engl. J. Med. 337:1997;734-739.
41. Hammer S.M., Squires K.E., Hughes M.D.et al. A controlled trial of two nucleoside analogues plus indinavir in person with human immunodeficiency virus infection and CD4 cell counts of 200 per cubic millimeter or less. New Engl. J. Med. 337:1997;725-733.
42. Hart G.J., Orr D.C., Penn C.R.et al. Effects of (-)-2′-deoxy-3′-thiacytidine (3TC) 5′-triphosphate on human immunodeficiency virus reverse transcriptase and mammalian DNA polymerase α, β, and γ Antiviral Chem. Chemother. 36:1992;1688-1694.
43. Hashimmoto Y., Iwanami N., Fujimori S., Shudo K. Enantio- and meso-DNAs: preparation, characterization, interaction with complementary nucleic acid. J. Am. Chem. Soc. 115:1993;9883-9887.
44. Holy A., Sorm F. Preparation of some β-L-ribonucleosides, their 2′,3′-cyclic phosphates. Collect. Czech. Chem. Commun. 34:1969;3383-3391.
45. Holy, A., 1971. A synthesis of 2′-deoxy-L-uridine. Tetrahedron Lett., pp. 189-193.
46. Holy A. Preparation of 2′-deoxy-L-ribonucleosides of the pyrimidine series. Collect. Czech. Chem. Commun. 37:1972;4072-4082.
47. Imbach, J.-L., Gosselin, G., Mathe, C., et al., 1998. L-Purine prodrugs as inhibitors of HIV replication. 11th International Conference on Antiviral Research, 5-10 April, San diego, Califonia.
48. Jeong L.S., Schinazi R.F., Beach J.W.et al. Structure-activity relationships of β-D-(2S,5R)- and α-D-(2S,5S)-1,3-oxathiolanyl nucleosides as potential anti-HIV agents. J. Med. Chem. 36:1993;2627-2638.
49. Jeong L.S., Schinazi R.F., Beach J.W.et al. Asymmetric synthesis and biological evaluation of β-L-(2R,5S)- and α-L-(2R,5S)-1,3-oxathiolane-pyrimidine and -purine nucleosides as potential anti-HIV agents. J. Med. Chem. 36:1993;181-195.
50. Jurovcik M., Holy A. Metabolism of pyrimidine L-nucleosides. Nucleic Acid Res. 3:1976;2143-2154.
51. Katlama C., Ingrand D., Loveday C.et al. Safety and efficacy of lamivudine-zidovudine combination therapy in antiretroviral-naive patients. J. Am. Med. Assoc. 276:1996;118-125.
52. Kim H.O., Shanmuganathan K., Alves A.J.et al. Potent anti-HIV and anti-HBV activities of (-)-L-β-dioxolane-C and (+)-L-β-dioxolane-T and their asymmetric synthesis. Tetrahedron lett. 33:1992;6899-6902.
53. Kim H.O., Schinazi R.F., Shanmuganathan K.et al. L-β-(2S,4S)- and L-α-(2S,4S)-Dioxolanyl nucleosides as potential anti-HIV agents: asymmetric synthesis and structure-activity relationships. J. Med. Chem. 36:1993;519-528.
54. Kim H.O., Schinazi R.F., Nampalli S.et al. 1,3-Dioxolanylpurine nucleosides (2S,4S) and (2S,4S) with selective anti-HIV-1 activity in human lymphocytes. J. Med. Chem. 36:1993;30-37.
55. Koszalka G.W., Chamberlain S.D., Harvey R.J. Benzimidazoles for the treatment of human cytomegalovirus. Antiviral Res. 30:1996;A43.
56. Kotra L.P., Xiang Y., Newton M.G., Schinazi R.F., Cheng Y.-C., Chu C.K. Structure-activity relationships of 2′-deoxy-2′,2″-difluoro-L-erythro-pentofuranosyl nucleosides. J. Med. Chem. 40:1997;3635-3644.
57. Lin T.-S., Luo M.-Z., Liu M.-C., Pai S.B., Dutschman G.E., Cheng Y.-C. Synthesis and biological evaluation of 2′,3′-dideoxy-L-pyrimidine nucleosides as potential antiviral agents against human immunodeficiency virus (HIV) and hepatitis B virus (HBV). J. Med. Chem. 37:1994;798-803.
58. Lin T.-S., Luo M.-Z., Liu M.-C. A stereospecific synthesis of 2′,3′-dideoxy-β-L-cytidine (β-L-ddC), a potent inhibitor against human hepatitis B virus (HBV) and human immunodeficiency virus (HIV). Tetrahedron Lett. 35:1994;3477-3480.
59. Lin T.-S., Luo M.-Z., Zhu J.-L.et al. Synthesis of a series of purine 2′,3′-dideoxy-L-nucleoside analogues as potential antiviral agents. Nucleosides Nucleotides. 14:1995;1759-1783.
60. Lin T.-S., Luo M.-Z., Liu M.-C. Synthesis of several pyrimidine L-nucleoside analogues as potential antiviral agents. Tetrahedron. 51:1995;1055-1068.
61. Lin T.-S., Luo M.-Z., Liu M.-C.et al. Design and synthesis of 2′,3′-dideoxy-2′,3′-didehydro-β-L-cytidine (β-L-d4C) and 2′,3′-dideoxy-2′,3′-didehydro-β-L-5-fluorocytidine (β-L-Fd4C) cytidine, two exceptionally potent inhibitors of human hepatitis B virus (HBV) and potent inhibitors of human immunodeficiency virus (HIV) in vitro. J. Med. Chem. 39:1996;1757-1759.
62. Liu S.H., Grove K.L., Cheng Y.-C. Unique metabolism of a novel antiviral L-nucleoside analog, L-FMAU: a substrate for both thymidine kinase and deoxycytidine kinase. Antimicrob. Agents Chemother. 42:1998;833-839.
63. Loi, A.G., Faraj, A., Pierre, C., et al., 1997. Evaluation of anti-HBV activity of β-D- and β-L-ddAMP-SATE prodrugs alone and in combination with Lamivudine. 2nd International conference on therapies for viral hepatitis, 15-19 December, Hawaii.
64. Ma T.W., Pai S.B., Zhu Y.-L. Structure-activity relationships of 1-(2-deoxy-2-fluoro-β-arabinofuranosyl)-pyrimidine nucleosides as anti-hepatitis B virus agents. J. Med. Chem. 39:1996;2835-2843.
65. Ma T.W., Lin J.-C., Newton M.G., Cheng Y.-C., Chu C.K. Synthesis and anti-hepatitis B virus activity of 9-(2-deoxy-2-fluoro-β-L-arabinofuranosyl)-purine nucleosides. J. Med. Chem. 40:1997;2750-2754.
66. Macilwain C. NIH, FDA seek lessons from the hepatitis B drug trial deaths. Nature. 364:1993;275.
67. Mahmoudian M., Bains B.S., Drake C.S.et al. Enzymatic production of optically pure (2′R-cis)-2′-deoxy-3′-thiacytidine (3TC, Lamivudine): a potent anti-HIV agent. Enzyme Microb. Technol. 15:1993;749-755.
68. Mansour T.S., Jin H., Wang W.et al. Anti-Human immunodeficiency virus and anti-hepatitis-B virus activities and toxicitities of the enantiomers of 2′- deoxy-3′-oxa-4′-thiocytidine and their 5-fluoro analogues in vitro. J. Med. Chem. 38:1995;1-4.
69. Mansuri M.M., Farina V., Starrett J.E., Benigni D.A., Brankovan V., Martin J.C. Preparation of the geometric isomers of ddC, ddA, d4C, and d4T as potential anti-HIV agents. Bioorg. Med. Chem. Lett. 1:1991;65-68.
70. Mansuri M.M., Starrett J.E., Wos J.A.et al. Preparation of 1-(2,3-dideoxy-β-D-glycero-pent-2-enofuranosyl) thymine (d4T) and 2′,3′-dideoxyadenosine (ddA): general methods for the synthesis of 2′,3′-olefinic and 2′,3′-dideoxy nucleoside analogues active against HIV. J. Org. Chem. 54:1989;4780-4785.
71. Merlo V., Roberts S.M., Storer R., Bethell R.C. Synthesis and biological activity of the diphosphorylphosphonate derivatives of (+)- and (-)-cis-9-(4′-hydroxycyclopent-2′-enyl)-guanine. J. Chem. Soc. Perkin Trans. 1:1994;1477-1481.
72. Miller W.H., Daluge S.M., Garvey E.P.et al. Phosphorylation of carbovir enantiomers by cellular enzyme determines the stereoselectivity of antiviral activity. J. Biol. Chem. 267:1992;21220-21224.
73. Morvan F., Génu C., Rayner B., Gosselin G., Imbach J.-L. Sugar modified oligonucleotides. III (1). Synthesis, nuclease resistance and base pairing properties of α-, and β-L-octathymidylates. Biochem. Biophys. Res. Commun. 172:1990;537-543.
74. Norbeck D.W., Spanton S., Broder S., Mitsuya H. (±)-Dioxolane-T ((±)-1-[(2β,4β)-2-(hydroxymethyl-4-dioxolanyl]-thymine). A new 2′,3′-dideoxy nucleoside prototype with in vitro activity against HIV. Tetrahedron Lett. 30:1989;6263-6266.
75. Okabe M., Sun R.C., Tara S.Y.K., Todaro L.J., Coffen D.L. Synthesis of the dideoxynucleosides ddC and CNT from glutamic acid, ribonolactone, and pyrimidine bases. J. Org. Chem. 53:1988;4780-4786.
76. Paff M.T., Averett D.R., Prus K.L., Miller W.H., Nelson D.J. Intracellular metabolism of (-)- and (+)-cis-5-fluoro-1-[2-(hydroxymethyl)-1,3- oxathiolan-5-yl]-cytosine in HepG2 derivative 2.2.15 (subclone p5A) cells. Antimicrob. Agents Chemother. 38:1994;1230-1238.
77. Pai S.B., Liu S.H., Zhu Y.L., Chu C.K., Cheng Y.C. Inhibition of hepeatitis B virus a novel L-nucleoside, 2′-fluoro-5-methyl-β-L-arabinofuranosyl uracil. Antimicrob. Agents Chemother. 40:1996;380-386.
78. Parker W.B., Cheng Y.-C. Mitochondrial toxicity of antiviral nucleoside analogues. J. Natl. Inst. Health Res. 6:1994;57-61.
79. Placidi, L., Perigaud, C., Cretton-Scott, E., et al., 1997. Cellular pharmacology of β-L-ddAMP-bis(tbutylSATE), a potent inhibitor of hepatitis B replication. 2nd International Conference on Therapies for Viral Hepatitis, 15-19 December, Hawaii.
80. èlicano et al., 1997.
81. Pèlicano H., Pierra C., Eriksson S., Gosselin G., Imbach J.-L., Maury G. Enzymatic properties of the unnatural β-L-enantiomers of 2′,3′-dideoxyadenosine and 2′,3′-didehydro-2′,3′-dideoxyadenosine. J. Med. Chem. 40:1997;3969-3973.
82. Rajagopalan, P.F., Boudinot, F.D., Chu, C.K., McClure, H.M., Schinazi, R.F., 1994. Pharmacokinetics of (-)-β-D-2,6-diaminopurine dioxolane and its metabolite dioxolane guanine in rhesus monkeys. Pharm. Res. 11, suppl. 381.
83. Ries S., Savithiry S., Wert V., Widders I. Rapid induction of ion pulses in tomato, cucumber, and maize plants following a foliar application of L-(+)-adenosine. Plant Physiol. 101:1993;49-55.
84. Robins M.J., Khwaja T.A., Robins R.K. Purine nucleoside. XXIX. The synthesis of 2′-deoxy-L-adenine and 2′-deoxy-L-guanosine and their α-anomer. J. Org. Chem. 34:1969;636-639.
85. Schinazi R.F., Chu C.K., Peck A.et al. Activities of the four optical isomers of 2′,3′-dideoxy-3′-thiacytidine (BCH-189) against human immunodeficiency virus type I in human lymphocytes. Antimicrob. Agents Chemother. 36:1992;672-676.
86. Schinazi R.F., McMillan A., Cannon D. Selective inhibition of human immonodeficiency viruses by racemates and enantiomers of cis-5-fluoro-1-[2-(hydroxymethyl)-1,3-oxathiolan-5-yl]-cytosine. Antimicrob. Agents Chemother. 36:1992;2423-2431.
87. Schinazi R.F., Boudinot F.D., Ibrahim S.S., Manning C., McClure H.M., Liotta D.C. Pharmacokinetics and metabolism of racemic 2′,3′-dideoxy-5-fluoro-3′-thiacytidine in rhesus monkeys. Antimicrob. Agents Chemother. 36:1992;2432-2438.
88. Schinazi, R.F., McClure, H.M., Boudinout, F.D., Xiang, Y.-J., Chu, C.K., 1994. Development of (-)-β-D-2,6-diaminopurine dioxolane as a potential antiviral agent. Antiviral Res. 23, suppl. 81.
89. Seley K.L., Schneller S.W., Rattendi D., Bacchi C.J. (+)-7-Deaza-5′-noraristeromycin as an anti-trypanosomal agent. J. Med. Chem. 40:1997;622-624.
90. Seley K.L., Schneller S.W., Korba B. A 5′-noraristeromycin enantiomer with activity towards hepatitis B virus. Nucleosides Nucleotides. 16:1997;2095-2099.
91. Severini A., Liu X.-Y., Wilson J.S., Tyrrell D.L.J. Mechanism of inhibition of duck hepatitis B virus polymerase by (-)-β-L-2′,3′-dideoxy-3′-thiacytidine. Antimicrob. Agents Chemother. 39:1995;1430-1435.
92. Shewach D.S., Liotta D.C., Schinazi R.F. Affinity of the antiviral enantiomers of oxathiolane cytosine nucleosides for human 2′-deoxycytidine kinase. Biochem. Pharmacol. 45:1993;1540-1543.
93. Silverton J.V., Quinn F.R., Haugwitz R.D., Todaro L.J. Structures of two dideoxynucleosides: 2′,3′-dideoxyadenosine and 2′,3′-dideoxycytidine. Acta Crystallogr. 44:1988;321-324.
94. Simuth J., Holy A. Nucleic Acids Res. Spec. Publ. No. 1:1975;s165-s168.
95. Smejkal J., Sorm F. Nucleic acid components and their analogues. LIII. Preparation of 1,2-deoxy-β-L-ribofuranosylthymine, 'L-thymine'. Collect. Czech. Chem. Commun. 29:1964;2809-2813.
96. Sommadossi J.-P., Schinazi R.F., Chu C.K., Xie M.-Y. Comparison of the cytotoxicity of the (-)- and (+)-enantiomer of 2′,3′-dideoxy-3′-thiacytidine in normal human bone marrow progenitor cells. Biochem Pharmacol. 44:1992;1921-1925.
97. Soudeyns H., Yao X.J., Gao Q. Anti-human immunodeficiency virus type 1 activity and in vitro toxicity of 2′-deoxy-3′-thiacytidine (BCH-189), a novel heterocyclic nucleoside analog. Antimicrob. Agents Chemother. 35:1991;1386-1390.
98. Spadari S., Maga G., Focher F.et al. L-Thymidine is phosphorylated by herpes simplex virus type 1 thymidine kinase and inhibits viral growth. J. Med. Chem. 35:1992;4214-4220.
99. Spadari S., Maga G., Verri A. Lack of stereospecificity of some cellular and viral enzymes involved in the synthesis of deoxyribonucleotides and DNA: molecular basis for the antiviral activity of unnatural L-β-nucleosides. Biochimie. 77:1995;861-867.
100. Staszewski S., Loveday C., Picazo J.et al. Safety and efficacy of lamivudine-zidovudine combination therapy in antiretroviral-experienced patients. J. Am. Med. Assoc. 276:1996;111-117.
101. éphanie et al., 1998.
102. Stéphanie A.-G., Liu S.H., Chevallier M. Inhibitory effect of 2′-fluoro-5-methyl-β-L arabinofuranosyl-uracil on duck hepatitis B virus replication. Antimicrob. Agents Chemother. 42:1998;369-376.
103. Storer R., Clemens I.R., Lamont B., Noble S.A., Williamson C., Belleau B. The resolution and absolute stereochemistry enantiomers of cis-1,2-hydroxymethyl-1,3-oxathiolan-5-yl-cytosine BCH-189 equipotent anti-HIV agents. Nucleosides Nucleotides. 12:1993;225-236.
104. Tanaka M., Norimine Y., Fujita T., Suemune H., Sakai K. Chemoenzymatic synthesis of antiviral carbocyclic nucleosides: asymmetric hydrolysis of meso-3,5-bis(acetoxymethyl)cyclopentenes using Rhizopus delemar lipase. J.Org. Chem. 61:1996;6952-6957.
105. Tennant B., Jacob J., Graham L.A., Peek S., Du J., Chu C.K. Pharmacokinetic and pharmacodynamic studies of 1-(2-fluoro-5-methyl-β-L-arabinofuranosyl)-uracil (L-FMAU) in the woodchuck model of hepatitis B virus (HBV) infection. Antiviral Res. 34(A52):1997;36.
106. Tino J.A., Clark J.M., Field A.K.et al. Synthesis and antiviral activity of novel isonucleoside analogs. J. Med. Chem. 36:1993;1221-1229.
107. Touchette N. HBV-drug deaths prompt restudy of similar antivirals. J. Natl. Inst. Health Res. 5:1993;33-36.
108. Van Draanen N.A., Tucker S.C., Boyd F.L., Trotter B.W., Reardon J.E. β-L-Thymidine-5′-triphosphate analogs as DNA polymerase. J. Biol. Chem. 267:1992;25019-25024.
109. Van Draanen N.A., Tisdale M., Parry N.R.et al. Influence of stereochemistry on antiviral activities and resistance profiles of dideoxycytidine nucleosides. Antimicrob. Agents Chemother. 38:1994;868-871.
110. Van Roey P., Pangborn W.A., Schinazi R.F., Painter G., Liotta D.C. Absolute configuration of the antiviral agent (-)-cis-5-fluoro-1-[2-(hydroxymethyl)-1,3-oxathiolan-5-yl]-cytosine. Antiviral Chem. Chemother. 4:1993;369-375.
111. Votruba I., Holy A., Sorm F. L-Ribonucleosides do not penetrate bacterial cell walls. FEBS Lett. 19:1971;136-138.
112. Wang, P.Y., Schinazi, R.F., Chu, C.K., 1998. Asymmetric synthesis and anti-HIV activity of L-carbocyclic 2′,3′-didehydro-2′,3′-dideoxyadenosine. Bioorg. Med. Chem. Lett. in press.
113. Watanabe K.A., Reichman U., Hirota K., Lopez C., Fox J.J. Synthesis and antiherpes virus activity of some 2′-fluoro-2′-deoxy-arabinofuranosylpyrimidine nucleosides. J. Med. Chem. 22:1979;21-24.
114. Watanabe K.A., Su T.-L., Klein R.S.et al. Synthesis of antiviral nucleosides, 5-substituted 1-(2-deoxy-2-halogeno-β-D-arabinofuranosyl)-cytosines and uracils, some structure-activity relationships. J. Med. Chem. 26:1983;152-156.
115. Wengel J., Lau J., Pederson E.B., Nielson C.M. Synthesis of L-3′-azido-3′-deoxythymidine and its stereoisomers. J. Org. Chem. 56:1991;3591-3594.
116. Witcher J.W., Boudinot F.D., Baldwin B.H.et al. Pharmacokinetics of 1-(2-fluoro-5-methyl-β-L-arabinofuranosyl)-uracil (L-FMAU) in woodchucks. Antimicrob. Agents Chemother. 41:1997;2184-2187.
117. Wright J.D., Ma T.-W., Chu C.K., Boudinot F.D. Discontinuous oral absorption pharmacokinetic model and bioavailability of 1-(2-fluoro-5-methyl-β- L-arabinofuranosyl)-uracil (L-FMAU) in rats. Biopharm. Drug Disposit. 17:1996;197-207.
118. Xiang Y., Cavalcanti S., Chu C.K.et al. Anti-human immunodeficiency virus type-1 (HIV-1) and anti- hepatitis B virus (HBV) activities of (2,3-dideoxy-2-fluoro-β-L-threo pentofuranosyl)-nucleosides. Bioorg. Med. Chem. Lett. 5:1995;877-880.
119. Yao G.-Q., Liu S.H., Chou E., Kukhanova M., Chu C.K., Cheng Y.C. Inhibition of Epstein-Barr virus replication by a novel L-nucleoside, 2′-fluoro-5-methyl-β-L-arabinofuranosyl uracil. Biochem. Pharm. 51:1996;941-947.
120. Young R.J., Ponter-Shaw S., Thomson J.B.et al. Synthesis and antiviral evaluation of enantiomeric 2′,3′-dideoxy and 2′,3′-didehydro-2′,3′-dideoxy-4′-thionucleosides. Bioorg. Med. Chem. Lett. 5:1995;2599-2604.