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Volumn 43, Issue 1, 1996, Pages 53-64

Synthetic and biological applications of tricyclic analogues of guanosine

Author keywords

1D 1H NOE differential spectroscopy; Acyclovir; Antiviral activity; Ganciclovir; Syn anti conformational analysis; Tricyclic derivatives of guanosine and 2 deoxyguanosine; Wyosine; Y nucleosides

Indexed keywords

ACICLOVIR; ANTIVIRUS AGENT; BACTERIAL DNA; DNA; DRUG DERIVATIVE; GANCICLOVIR; GUANINE; GUANOSINE; PHENYLALANINE TRANSFER RNA; WYE; WYOSINE;

EID: 0029688509     PISSN: 0001527X     EISSN: None     Source Type: Journal    
DOI: 10.18388/abp.1996_4541     Document Type: Article
Times cited : (2)

References (47)
  • 1
    • 0016225445 scopus 로고
    • Transfer RNA and protein synthesis
    • Rich, A. (1974) Transfer RNA and protein synthesis. Biochemie 56, 1441-1449.
    • (1974) Biochemie , vol.56 , pp. 1441-1449
    • Rich, A.1
  • 2
    • 0016611690 scopus 로고
    • Structure of the fluorescent nucleoside of yeast phenylalanine transfer ribonucleic acid
    • and references therein
    • Blobstein, S.H., Gebert, R., Grunberger, D., Nakanishi, K. & Weinstein, I.B. (1975) Structure of the fluorescent nucleoside of yeast phenylalanine transfer ribonucleic acid. Arch. Biochem. Biophys. 167, 668-673 and references therein.
    • (1975) Arch. Biochem. Biophys. , vol.167 , pp. 668-673
    • Blobstein, S.H.1    Gebert, R.2    Grunberger, D.3    Nakanishi, K.4    Weinstein, I.B.5
  • 9
    • 0014428762 scopus 로고
    • A specific modification next to the anticodon of phenylalanine transfer ribonucleic acid
    • Thiebe, R. & Zachau, H.G. (1968) A specific modification next to the anticodon of phenylalanine transfer ribonucleic acid. Eur. J. Biochem. 5, 546-555.
    • (1968) Eur. J. Biochem. , vol.5 , pp. 546-555
    • Thiebe, R.1    Zachau, H.G.2
  • 10
    • 0038385327 scopus 로고
    • A simple synthesis of 3-β-D-ribofuranosylwye and the stability of its glycosidic bond
    • Itaya, T., Watanabe, T. & Matsumoto, H. (1980) A simple synthesis of 3-β-D-ribofuranosylwye and the stability of its glycosidic bond. J. Chem. Soc. Chem. Commun. 1158-1159.
    • (1980) J. Chem. Soc. Chem. Commun. , pp. 1158-1159
    • Itaya, T.1    Watanabe, T.2    Matsumoto, H.3
  • 11
    • 0020667670 scopus 로고
    • Alterations in post-transcriptional modification of the Ybase in phenylalanine tRNA from tumor cells
    • and references therein
    • Grunberger, D., Pergolizzi, R.G., Kuchino, Y., Mushinski, J.F. & Nishimura, S. (1983) Alterations in post-transcriptional modification of the Ybase in phenylalanine tRNA from tumor cells. Recent Results in Cancer Res. 84, 133-145 and references therein.
    • (1983) Recent Results in Cancer Res. , vol.84 , pp. 133-145
    • Grunberger, D.1    Pergolizzi, R.G.2    Kuchino, Y.3    Mushinski, J.F.4    Nishimura, S.5
  • 12
    • 0016275714 scopus 로고
    • Antibodies to yeast phenylalanine transfer ribonucleic acid are specific for the odd nucleoside Y in the anticodon loop
    • Fuchs, S., Aharonov, A., Sela, M., von der Haar, F. & Cramer, F. (1974) Antibodies to yeast phenylalanine transfer ribonucleic acid are specific for the odd nucleoside Y in the anticodon loop. Proc. Natl. Acad. Sci. U.S.A. 71, 2800-2802.
    • (1974) Proc. Natl. Acad. Sci. U.S.A. , vol.71 , pp. 2800-2802
    • Fuchs, S.1    Aharonov, A.2    Sela, M.3    Von Der Haar, F.4    Cramer, F.5
  • 13
  • 14
    • 0018799842 scopus 로고
    • Proton nuclear magnetic resonance of minor nucleosides in yeast phenylalanine transfer ribonucleic acid. Conformational changes as a consequence of aminoacylation. Removal of the Ybase, and codon-anticodon interaction
    • and references therein
    • Davanloo, P., Sprinzl, M. & Cramer, F. (1979) Proton nuclear magnetic resonance of minor nucleosides in yeast phenylalanine transfer ribonucleic acid. Conformational changes as a consequence of aminoacylation. Removal of the Ybase, and codon-anticodon interaction. Biochemistry 18, 3189-3199 and references therein.
    • (1979) Biochemistry , vol.18 , pp. 3189-3199
    • Davanloo, P.1    Sprinzl, M.2    Cramer, F.3
  • 15
    • 0019561164 scopus 로고
    • Phe anticodon loop occur upon aminoacylation as indicated by Ybase fluorescence
    • Phe anticodon loop occur upon aminoacylation as indicated by Ybase fluorescence. J. Biochem. 89, 1439-1443.
    • (1981) J. Biochem. , vol.89 , pp. 1439-1443
    • Okabe, N.1    Cramer, F.2
  • 16
    • 0021769672 scopus 로고
    • Phe anticodon loop monitored by fluorescence
    • Phe anticodon loop monitored by fluorescence. Nucleic Acids Res. 12, 2157-2170.
    • (1984) Nucleic Acids Res. , vol.12 , pp. 2157-2170
    • Wells, B.D.1
  • 18
    • 0006486728 scopus 로고
    • Synthesis of 3,9-dialkylguanines and 3-methylguanosine, a key intermediate for the synthesis of Y nucleosides
    • Itaya, T. & Ogawa, K. (1978) Synthesis of 3,9-dialkylguanines and 3-methylguanosine, a key intermediate for the synthesis of Y nucleosides. Tetrahedron Lett. 2907-2910.
    • (1978) Tetrahedron Lett. , pp. 2907-2910
    • Itaya, T.1    Ogawa, K.2
  • 19
    • 85009635383 scopus 로고
    • Synthesis of 3-β-D-ribofuranosylwye, the most probable structure for wyosine from Torulopsis utilis phenylalanine transfer ribonucleic acid
    • Itaya, T., Matsumoto, K., Watanabe, T. & Harada, T. (1985) Synthesis of 3-β-D-ribofuranosylwye, the most probable structure for wyosine from Torulopsis utilis phenylalanine transfer ribonucleic acid. Chem. Pharm. Bull. 36, 2339-2347.
    • (1985) Chem. Pharm. Bull. , vol.36 , pp. 2339-2347
    • Itaya, T.1    Matsumoto, K.2    Watanabe, T.3    Harada, T.4
  • 20
    • 0015766214 scopus 로고
    • Biosynthetic studies of the Y base in yeast phenylalanine tRNA. Incorporation of guanine
    • Li, H.J., Nakanishi, K., Grunberger, D. & Weinstein, I.B. (1973) Biosynthetic studies of the Y base in yeast phenylalanine tRNA. Incorporation of guanine. Biochem. Biophys. Res. Commun. 53, 818-823.
    • (1973) Biochem. Biophys. Res. Commun. , vol.53 , pp. 818-823
    • Li, H.J.1    Nakanishi, K.2    Grunberger, D.3    Weinstein, I.B.4
  • 22
    • 0021101151 scopus 로고
    • Methylation of desmethyl analogue of Y nucleoside. Wyosine from guanosine
    • and references therein
    • Golankiewicz, B. & Folkman, W. (1983) Methylation of desmethyl analogue of Y nucleoside. Wyosine from guanosine. Nucleic Acids Res. 11, 5243-5255 and references therein.
    • (1983) Nucleic Acids Res. , vol.11 , pp. 5243-5255
    • Golankiewicz, B.1    Folkman, W.2
  • 24
    • 33947467473 scopus 로고
    • A new synthesis of cyclopropanes from olefins
    • Simmons, H.E. & Smith, R.D. (1958) A new synthesis of cyclopropanes from olefins. J. Am. Chem. Soc. 80, 5323-5324.
    • (1958) J. Am. Chem. Soc. , vol.80 , pp. 5323-5324
    • Simmons, H.E.1    Smith, R.D.2
  • 25
    • 0039901711 scopus 로고
    • A new synthesis of cyclopropanes
    • Simmons, H.E. & Smith, R.D. (1959) A new synthesis of cyclopropanes. J. Am. Chem. Soc. 81, 4256-4264.
    • (1959) J. Am. Chem. Soc. , vol.81 , pp. 4256-4264
    • Simmons, H.E.1    Smith, R.D.2
  • 27
    • 0000008041 scopus 로고
    • A comparison of (chloromethyl)- and (iodomethyl) zinc cyclopropanation reagents
    • and references therein
    • Denmark, S.E. & Edwards, J.P. (1991 ) A comparison of (chloromethyl)- and (iodomethyl) zinc cyclopropanation reagents. J. Org. Chem. 56, 6974-6981 and references therein.
    • (1991) J. Org. Chem. , vol.56 , pp. 6974-6981
    • Denmark, S.E.1    Edwards, J.P.2
  • 28
    • 0023749493 scopus 로고
    • A novel route to 3-methylguanosine by chemical degradation of wyosine
    • Boryski, J., Folkman, W. & Golankiewicz, B. (1988) A novel route to 3-methylguanosine by chemical degradation of wyosine. Tetrahedron Lett. 29, 4163-4164.
    • (1988) Tetrahedron Lett. , vol.29 , pp. 4163-4164
    • Boryski, J.1    Folkman, W.2    Golankiewicz, B.3
  • 29
    • 0022345211 scopus 로고
    • A new simple synthesis of N-2-methylguanosine and its analogues via derivatives of 4-desmethylwyosine
    • and references therein
    • Boryski, J., Ueda, T. (1985) A new simple synthesis of N-2-methylguanosine and its analogues via derivatives of 4-desmethylwyosine. Nucleosides & Nucleotides 4, 595-606 and references therein.
    • (1985) Nucleosides & Nucleotides , vol.4 , pp. 595-606
    • Boryski, J.1    Ueda, T.2
  • 30
    • 0025148858 scopus 로고
    • Synthesis and properties of oligodeoxy-nucleotide containing a polycyclic aromatic hydrocarbon site specifically bound to the N amino group of a 2′-deoxyguanosine residue
    • and references therein
    • Casale, R. & McLaughlin, L.W. (1990) Synthesis and properties of oligodeoxy-nucleotide containing a polycyclic aromatic hydrocarbon site specifically bound to the N amino group of a 2′-deoxyguanosine residue. J. Am. Chem. Soc. 112, 5264-5271 and references therein.
    • (1990) J. Am. Chem. Soc. , vol.112 , pp. 5264-5271
    • Casale, R.1    McLaughlin, L.W.2
  • 31
    • 1542480830 scopus 로고
    • Application of the 1,N-2-isopropenoguanosine system for synthesis of novel N-2 substituted derivatives of guanosine and acyclovir
    • Boryski, J. (1990) Application of the 1,N-2-isopropenoguanosine system for synthesis of novel N-2 substituted derivatives of guanosine and acyclovir. Collect. Czech. Chem. Commun. 55, Special Issue 1, 85-88.
    • (1990) Collect. Czech. Chem. Commun. , vol.55 , Issue.1 SPEC. ISSUE , pp. 85-88
    • Boryski, J.1
  • 32
    • 0025044901 scopus 로고
    • Chemical synthesis and spontaneous glycosidic hydrolysis of 3-methyl-2′-deoxyguano-sine and 2′-deoxywyosine
    • Golankiewicz, B., Ostrowski, T. & Folkman, W. (1990) Chemical synthesis and spontaneous glycosidic hydrolysis of 3-methyl-2′-deoxyguano-sine and 2′-deoxywyosine. Nucleic Acids Res. 18, 4779-4782.
    • (1990) Nucleic Acids Res. , vol.18 , pp. 4779-4782
    • Golankiewicz, B.1    Ostrowski, T.2    Folkman, W.3
  • 33
    • 0006479572 scopus 로고
    • 13C NMR spectra of wyosine, a hypermodified nucleoside of transfer RNAs, and related compounds
    • 13C NMR spectra of wyosine, a hypermodified nucleoside of transfer RNAs, and related compounds. Magn. Reson. Chem. 23, 920-924.
    • (1985) Magn. Reson. Chem. , vol.23 , pp. 920-924
    • Golankiewicz, B.1    Folkman, W.2
  • 35
    • 0015333450 scopus 로고
    • Reaction of alkylating mutagens and carcinogens with nucleic acids. N-3 of guanine as a site of alkylation by N-methyl-N-nitrosourea and dimethyl sulfate
    • Lawley, P.D., Orr, D.J. & Shah, S.A. (1972) Reaction of alkylating mutagens and carcinogens with nucleic acids. N-3 of guanine as a site of alkylation by N-methyl-N-nitrosourea and dimethyl sulfate. Chem.-Biol. Interact. 4, 431-434.
    • (1972) Chem.-Biol. Interact. , vol.4 , pp. 431-434
    • Lawley, P.D.1    Orr, D.J.2    Shah, S.A.3
  • 36
    • 0017257991 scopus 로고
    • Removal of minor methylation products 7-methyladenine and 3-methylguanine from DNA of Escherichia coli treated with dimethyl sulfate
    • Lawley, P.D. & Warren, W. (1976) Removal of minor methylation products 7-methyladenine and 3-methylguanine from DNA of Escherichia coli treated with dimethyl sulfate. Chem.-Biol. Internet. 12, 211-220.
    • (1976) Chem.-Biol. Internet. , vol.12 , pp. 211-220
    • Lawley, P.D.1    Warren, W.2
  • 40
    • 0024554561 scopus 로고
    • The purine pathway to chemotherapy
    • a review
    • Elion, G.B. (1989) The purine pathway to chemotherapy. Science 244, 41-46, a review.
    • (1989) Science , vol.244 , pp. 41-46
    • Elion, G.B.1
  • 41
    • 0028364918 scopus 로고
    • Antiviral activity spectrum and target of action of different classes of nucleoside analogues
    • a review
    • De Clercq, E. (1994) Antiviral activity spectrum and target of action of different classes of nucleoside analogues. Nucleosides & Nucleotides 13, 1271-1295, a review.
    • (1994) Nucleosides & Nucleotides , vol.13 , pp. 1271-1295
    • De Clercq, E.1
  • 42
    • 0022532716 scopus 로고
    • Chemistry and antiviral activities of acyclonucleosides
    • a review
    • Chu, C.K. & Cutler, S.J. (1986) Chemistry and antiviral activities of acyclonucleosides. J. Heterocyd. Chem. 23, 289-319, a review.
    • (1986) J. Heterocyd. Chem. , vol.23 , pp. 289-319
    • Chu, C.K.1    Cutler, S.J.2
  • 44
    • 0023793053 scopus 로고
    • Synthesis and antiviral activity of novel N-substituted derivatives of acyclovir
    • Boryski, J., Golankiewicz, B. & De Clercq, E. (1988) Synthesis and antiviral activity of novel N-substituted derivatives of acyclovir. J. Med. Chem. 31, 1351-1355.
    • (1988) J. Med. Chem. , vol.31 , pp. 1351-1355
    • Boryski, J.1    Golankiewicz, B.2    De Clercq, E.3
  • 45
    • 37049070563 scopus 로고
    • Synthesis of acyclowyosine and acyclo-3-methylguanosine as probes for some chemical and biological properties resulting from the N-3 substitution of guanosine and its analogues
    • Golankiewicz, B., Ostrowski, T., Boryski, J. & De Clercq,E. (1991) Synthesis of acyclowyosine and acyclo-3-methylguanosine as probes for some chemical and biological properties resulting from the N-3 substitution of guanosine and its analogues. J. Chem. Soc. Perkin Trans. I, 589-593.
    • (1991) J. Chem. Soc. Perkin Trans. , vol.1 , pp. 589-593
    • Golankiewicz, B.1    Ostrowski, T.2    Boryski, J.3    De Clercq, E.4
  • 46
    • 0026063209 scopus 로고
    • Synthesis and antiviral activity of 3-substituted derivatives of 3,9-dihydro-9-oxo-5H-imidazo[1,2-a]purines, tricyclic analogues of acyclovir and ganciclovir
    • Boryski, J., Golankiewicz, B. & De Clercq, E. (1991) Synthesis and antiviral activity of 3-substituted derivatives of 3,9-dihydro-9-oxo-5H-imidazo[1,2-a]purines, tricyclic analogues of acyclovir and ganciclovir. J. Med. Chem. 34, 2380-2383.
    • (1991) J. Med. Chem. , vol.34 , pp. 2380-2383
    • Boryski, J.1    Golankiewicz, B.2    De Clercq, E.3
  • 47
    • 0027970583 scopus 로고
    • Tricyclic analogues of acyclovir and ganciclovir. Influence of substitueras in the heterocyclic moiety on the antiviral activity
    • Golankiewicz, B., Ostrowski, T., Andrei, G., Snoek, R. & De Clercq, E. (1994) Tricyclic analogues of acyclovir and ganciclovir. Influence of substitueras in the heterocyclic moiety on the antiviral activity. J. Med. Chem. 37, 3187-3190.
    • (1994) J. Med. Chem. , vol.37 , pp. 3187-3190
    • Golankiewicz, B.1    Ostrowski, T.2    Andrei, G.3    Snoek, R.4    De Clercq, E.5


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