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Volumn 23, Issue 11, 2004, Pages 1683-1705

Nucleosidyl-O-methylphosphonates: A pool of monomers for modified oligonucleotides

Author keywords

Isopolar oligonucleotides; Non isosteric internucleotide linkage; Nucleoside phosphonates; Nucleotide analogs; P C linkage; Pentofuranosylthymine derivatives; Protection; Regioizomers

Indexed keywords

1 (2 DEOXY BETA DEXTRO PENTOFURANOSYL)THYMINE; 1 (3 DEOXY BETA DEXTRO ERYTHROPENTOFURANOSYL)THYMINE; 1 (3 DEOXY BETA DEXTRO PENTOFURANOSYL)THYMINE; 2' O PHOSPHONOMETHYL DERIVATIVE; 4 METHOXY 1 OXIDO 2 PYRIDYLMETHYL ESTER; DEOXYRIBONUCLEOSIDE; ESTER DERIVATIVE; MONOMER; NUCLEOSIDYL O METHYLPHOSPHONATE; OLIGONUCLEOTIDE; PHOSPHONIC ACID DERIVATIVE; THYMINE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 9644281562     PISSN: 15257770     EISSN: None     Source Type: Journal    
DOI: 10.1081/NCN-200033912     Document Type: Article
Times cited : (14)

References (25)
  • 1
    • 0011248958 scopus 로고
    • A convenient method for stepwise synthesis of oligothymidylate derivatives in large-scale quantities
    • Letsinger, R.L.; Ogilvie, K.K. A convenient method for stepwise synthesis of oligothymidylate derivatives in large-scale quantities. J. Am. Chem. Soc. 1967, 98, 4801-4803.
    • (1967) J. Am. Chem. Soc. , vol.98 , pp. 4801-4803
    • Letsinger, R.L.1    Ogilvie, K.K.2
  • 2
    • 0020480724 scopus 로고
    • New effective method for the synthesis of oligonucleotides via phosphotriester intermediates
    • Efimov, V.A.; Reverdatto, S.V.; Chakhmakhcheva, O.G. New effective method for the synthesis of oligonucleotides via phosphotriester intermediates. Nucleic Acids Res. 1982, 10 (21), 6675-6694.
    • (1982) Nucleic Acids Res. , vol.10 , Issue.21 , pp. 6675-6694
    • Efimov, V.A.1    Reverdatto, S.V.2    Chakhmakhcheva, O.G.3
  • 3
    • 0021100326 scopus 로고
    • Rapid synthesis of long-chain deoxyribooligonucleotides by the N-methylimidazolide phosphotriester method
    • Efimov, V.A.; Buryakova, A.A.; Reverdatto, S.V.; Chakhmakhcheva, O.G.; Ovchinnikov, Y.A. Rapid synthesis of long-chain deoxyribooligonucleotides by the N-methylimidazolide phosphotriester method. Nucleic Acids Res. 1983, 11 (23), 8369-8387.
    • (1983) Nucleic Acids Res. , vol.11 , Issue.23 , pp. 8369-8387
    • Efimov, V.A.1    Buryakova, A.A.2    Reverdatto, S.V.3    Chakhmakhcheva, O.G.4    Ovchinnikov, Y.A.5
  • 4
    • 0021769679 scopus 로고
    • General scheme of the phosphotriester condensation in the oligodeoxyribonucleotide synthesis with arylsulfonyl chlorides and arylsulfonyl azolides
    • Zarytova, V.F.; Knorre, D.G. General scheme of the phosphotriester condensation in the oligodeoxyribonucleotide synthesis with arylsulfonyl chlorides and arylsulfonyl azolides. Nucleic Acids Res. 1984, 12 (4), 2091-2110.
    • (1984) Nucleic Acids Res. , vol.12 , Issue.4 , pp. 2091-2110
    • Zarytova, V.F.1    Knorre, D.G.2
  • 6
    • 0028902797 scopus 로고
    • A new approach to the synthesis of the 5′-deoxy-5′- methylphosphonate linked thymidine oligonucleotide analogs
    • Szabó, T.; Kers, A.; Stawinski, J. A new approach to the synthesis of the 5′-deoxy-5′-methylphosphonate linked thymidine oligonucleotide analogs. Nucleic Acids Res. 1995, 23 (6), 893-900.
    • (1995) Nucleic Acids Res. , vol.23 , Issue.6 , pp. 893-900
    • Szabó, T.1    Kers, A.2    Stawinski, J.3
  • 9
    • 0031437170 scopus 로고    scopus 로고
    • Synthesis and binding properties of oligodeoxynucleotides containing phenylphosphon(othio)ate linkages
    • Mag, M.; Muth, J.; Jahn, K.; Peyman, A.; Kretzschmar, G.; Engels, J.W.; Uhlmann, E. Synthesis and binding properties of oligodeoxynucleotides containing phenylphosphon(othio)ate linkages. Bioorg. Med. Chem. 1997, 5 (12), 2213-2220.
    • (1997) Bioorg. Med. Chem. , vol.5 , Issue.12 , pp. 2213-2220
    • Mag, M.1    Muth, J.2    Jahn, K.3    Peyman, A.4    Kretzschmar, G.5    Engels, J.W.6    Uhlmann, E.7
  • 11
    • 0001878363 scopus 로고
    • The para-nitrophenylethyl (Npe) group - A versatile new blocking group for phosphate and aglycone protection in nucleosides and nucleotides
    • Himmelsbach, F.; Schulz, B.S.; Trichtinger, T.; Charubala, R.; Pfleiderer, W. The para-nitrophenylethyl (Npe) group - a versatile new blocking group for phosphate and aglycone protection in nucleosides and nucleotides. Tetrahedron 1984, 40 (1), 59-72.
    • (1984) Tetrahedron , vol.40 , Issue.1 , pp. 59-72
    • Himmelsbach, F.1    Schulz, B.S.2    Trichtinger, T.3    Charubala, R.4    Pfleiderer, W.5
  • 12
    • 0025310687 scopus 로고
    • Improved synthesis of oligodeoxyribonucleotides
    • Stengele, K.P.; Pfleiderer, W. Improved synthesis of oligodeoxyribonucleotides. Tetrahedron Lett. 1990, 31 (18), 2549-2552.
    • (1990) Tetrahedron Lett. , vol.31 , Issue.18 , pp. 2549-2552
    • Stengele, K.P.1    Pfleiderer, W.2
  • 13
    • 0026553940 scopus 로고
    • Convenient method for the preparation of trityl ethers from secondary alcohols
    • Collinmessager, S.; Girard, J.P.; Rossi, J.C. Convenient method for the preparation of trityl ethers from secondary alcohols. Tetrahedron Lett. 1992, 33 (19), 2689-2692.
    • (1992) Tetrahedron Lett. , vol.33 , Issue.19 , pp. 2689-2692
    • Collinmessager, S.1    Girard, J.P.2    Rossi, J.C.3
  • 14
    • 33947483704 scopus 로고
    • Studies on polynucleotides XXIV. The stepwise synthesis of specific deoxyribopolynucleotides. Protected derivatives of deoxyribonucleotides and new syntheses of deoxyribonucleoside-3′ phosphonates
    • Shaler, H.; Weimann, G.; Lerch, B.; Khorana, H.G. Studies on polynucleotides XXIV. The stepwise synthesis of specific deoxyribopolynucleotides. Protected derivatives of deoxyribonucleotides and new syntheses of deoxyribonucleoside-3′ phosphonates. Am. Chem. Soc. 1963, 85, 3821-3827.
    • (1963) Am. Chem. Soc. , vol.85 , pp. 3821-3827
    • Shaler, H.1    Weimann, G.2    Lerch, B.3    Khorana, H.G.4
  • 15
    • 0001003363 scopus 로고
    • Preparation of 5′-O-phosphonylmethyl analogs of nucleoside-5′-phosphates, 5′-diphosphates and 5′-triphosphates
    • Holý, A.; Rosenberg, I. Preparation of 5′-O-phosphonylmethyl analogs of nucleoside-5′-phosphates, 5′-diphosphates and 5′-triphosphates. Collect. Czechoslov. Chem. Commun. 1982, 47 (12), 3447-3463.
    • (1982) Collect. Czechoslov. Chem. Commun. , vol.47 , Issue.12 , pp. 3447-3463
    • Holý, A.1    Rosenberg, I.2
  • 16
    • 0034345905 scopus 로고    scopus 로고
    • Large-scale synthesis of a key catalytic reagent for phosphorus protection in building blocks for isopolar phosphonate oligonucleotide preparation
    • Rejman, D.; Erbs, J.; Rosenberg, I. Large-scale synthesis of a key catalytic reagent for phosphorus protection in building blocks for isopolar phosphonate oligonucleotide preparation. Org. Process Res. Dev. 2000, 4, 473-476.
    • (2000) Org. Process Res. Dev. , vol.4 , pp. 473-476
    • Rejman, D.1    Erbs, J.2    Rosenberg, I.3
  • 17
    • 9644285551 scopus 로고
    • Esters of arylsulfonic acids
    • Voloshin, V. Esters of arylsulfonic acids. Zh. Obshch. Khim. 1975, 45, 1121-1123.
    • (1975) Zh. Obshch. Khim. , vol.45 , pp. 1121-1123
    • Voloshin, V.1
  • 18
    • 0028366060 scopus 로고
    • Nucleic-acid analogs with restricted conformational flexibility in the sugar-phosphate backbone (bicyclo-Dna). Synthesis, pairing properties, and calorimetric determination of duplex and triplex stability of decanucleotides from (3′s,5′r)-2′-deoxy-3′,5′-ethano-beta-D- ribofuranosyl]adenine and thymine
    • Tarkoy, M.; Bolli, M.; Leumann, C. Nucleic-acid analogs with restricted conformational flexibility in the sugar-phosphate backbone (bicyclo-Dna). Synthesis, pairing properties, and calorimetric determination of duplex and triplex stability of decanucleotides from (3′s,5′r)-2′-deoxy- 3′,5′-ethano-beta-D-ribofuranosyl]adenine and thymine. Helv. Chim. Acta 1994, 77, 716-744.
    • (1994) Helv. Chim. Acta , vol.77 , pp. 716-744
    • Tarkoy, M.1    Bolli, M.2    Leumann, C.3
  • 19
    • 0000695695 scopus 로고
    • Synthesis of deoxy sugars-deoxygenation by treatment with N,N′-thiocarbonyldiimidazole-trinormal-butylstannane
    • Rasmussen, J.R.; Slinger, C.J.; Kordish, R.J.; Newman-Evans, D.D. Synthesis of deoxy sugars-deoxygenation by treatment with N,N′- thiocarbonyldiimidazole-trinormal-butylstannane. J. Org. Chem. 1981, 46 (24), 4843-4846.
    • (1981) J. Org. Chem. , vol.46 , Issue.24 , pp. 4843-4846
    • Rasmussen, J.R.1    Slinger, C.J.2    Kordish, R.J.3    Newman-Evans, D.D.4
  • 20
    • 9644292457 scopus 로고
    • Phosphorylated sugars. Part X. A simple synthesis of 3-deoxy-D-erythro- penthose 5-(dihydrogen phosphate)
    • Szabo, P.; Szabo, L. Phosphorylated sugars. Part X. A simple synthesis of 3-deoxy-D-erythro-penthose 5-(dihydrogen phosphate). J. Chem. Soc. 1965, 528, 2944-2947.
    • (1965) J. Chem. Soc. , vol.528 , pp. 2944-2947
    • Szabo, P.1    Szabo, L.2
  • 21
    • 0021171455 scopus 로고
    • Synthesis of amphotericin-B. 1. Fragment-A of the aglycon
    • Masamune, S.; Ma, P.; Okumoto, H.; Ellingboe, J.W.; Ito, Y. Synthesis of amphotericin-B. 1. Fragment-A of the aglycon. J. Org. Chem. 1984, 49 (15), 2834-2837.
    • (1984) J. Org. Chem. , vol.49 , Issue.15 , pp. 2834-2837
    • Masamune, S.1    Ma, P.2    Okumoto, H.3    Ellingboe, J.W.4    Ito, Y.5
  • 22
    • 0026741456 scopus 로고
    • 3′-Deoxy-2′-phosphoramidites of adenosine and 5-methyluridine used for the solid-phase synthesis of unnatural 3′-deoxy-2′- 5′-oligonucleotides
    • Carmelo, R.J.; Dougherty, J.P.; Breslow, R. 3′-Deoxy-2′- phosphoramidites of adenosine and 5-methyluridine used for the solid-phase synthesis of unnatural 3′-deoxy-2′-5′-oligonucleotides. Tetrahedron Lett. 1992, 33 (29), 4129-4132.
    • (1992) Tetrahedron Lett. , vol.33 , Issue.29 , pp. 4129-4132
    • Carmelo, R.J.1    Dougherty, J.P.2    Breslow, R.3
  • 24
    • 0025981030 scopus 로고
    • Synthesis of 2′-azido, 2,2′-anhydro and 2′,5′- anhydro nucleosides with potential anti-Hiv activity
    • Abdel-Megied, A.E.S.; Pedersen, E.B.; Nielsen, C.M. Synthesis of 2′-azido, 2,2′-anhydro and 2′,5′-anhydro nucleosides with potential anti-Hiv activity. Synthesis 1991, 4, 313-317.
    • (1991) Synthesis , vol.4 , pp. 313-317
    • Abdel-Megied, A.E.S.1    Pedersen, E.B.2    Nielsen, C.M.3
  • 25
    • 0023678725 scopus 로고
    • 1-(2,3-Anhydro-beta-D-lyxofuranosyl) cytosine derivatives as potential inhibitors of the human immunodeficiency virus
    • Webb, T.R.; Mitsuya, H.; Broder, S. 1-(2,3-Anhydro-beta-D-lyxofuranosyl) cytosine derivatives as potential inhibitors of the human immunodeficiency virus. J. Med. Chem. 1988, 31, 1475-1479.
    • (1988) J. Med. Chem. , vol.31 , pp. 1475-1479
    • Webb, T.R.1    Mitsuya, H.2    Broder, S.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.