메뉴 건너뛰기




Volumn 2, Issue 12, 2007, Pages 3122-3135

Synthesis of the 3 -thio-nucleosides and subsequent automated synthesis of oligodeoxynucleotides containing a 3 -s-phosphorothiolate linkage

Author keywords

[No Author keywords available]

Indexed keywords

NUCLEOSIDE; OLIGONUCLEOTIDE;

EID: 39149144824     PISSN: 17542189     EISSN: 17502799     Source Type: Journal    
DOI: 10.1038/nprot.2007.451     Document Type: Article
Times cited : (17)

References (31)
  • 1
    • 0026555646 scopus 로고
    • Sequence-specific and strand-specific cleavage in oligodeoxyribonucleotides and DNA containing 3'-thiothymidine
    • Vyle, J.S., Connolly, B.A., Kemp, D. & Cosstick, R. Sequence-specific and strand-specific cleavage in oligodeoxyribonucleotides and DNA containing 3'-thiothymidine. Biochemistry 31, 3012-3018 (1992).
    • (1992) Biochemistry , vol.31 , pp. 3012-3018
    • Vyle, J.S.1    Connolly, B.A.2    Kemp, D.3    Cosstick, R.4
  • 2
    • 0027398505 scopus 로고
    • Metal-ion catalysis in the Tetrahymena ribozyme reaction
    • Piccirilli, J.A., Vyle, J.S., Caruthers, M.H. & Cech, T.R. Metal-ion catalysis in the Tetrahymena ribozyme reaction. Nature 361, 85-88 (1993).
    • (1993) Nature , vol.361 , pp. 85-88
    • Piccirilli, J.A.1    Vyle, J.S.2    Caruthers, M.H.3    Cech, T.R.4
  • 3
    • 0029157302 scopus 로고
    • Sequence-specific binding of DNA by the EcoRV restriction and modification enzymes with nucleic-acid and cofactor analogues
    • Szczelkun, M.D. & Connolly, B.A. Sequence-specific binding of DNA by the EcoRV restriction and modification enzymes with nucleic-acid and cofactor analogues. Biochemistry 34, 10724-10733 (1995).
    • (1995) Biochemistry , vol.34 , pp. 10724-10733
    • Szczelkun, M.D.1    Connolly, B.A.2
  • 4
    • 0034639973 scopus 로고    scopus 로고
    • Inhibition of EcoRV endonuclease by deoxyribo-3'-S-phosphorothiolates: A high-resolution X-ray crystallographic study
    • Horton, N.C., Connolly, B.A. & Perona, J.J. Inhibition of EcoRV endonuclease by deoxyribo-3'-S-phosphorothiolates: a high-resolution X-ray crystallographic study. J. Am. Chem. Soc. 122, 3314-3324 (2000).
    • (2000) J. Am. Chem. Soc , vol.122 , pp. 3314-3324
    • Horton, N.C.1    Connolly, B.A.2    Perona, J.J.3
  • 5
    • 0030032337 scopus 로고    scopus 로고
    • 3'-Thiouridylyl-(3'-5')-uridine
    • Liu, X.H. & Reese, C.B. 3'-Thiouridylyl-(3'-5')-uridine. Tetrahedron Lett. 37, 925-928 (1996).
    • (1996) Tetrahedron Lett , vol.37 , pp. 925-928
    • Liu, X.H.1    Reese, C.B.2
  • 6
    • 0029844517 scopus 로고    scopus 로고
    • Synthesis and characterization of an RNA dinucleotide containing a 3'-S-phosphorothiolate linkage
    • Weinstein, L.B., Earnshaw, D.J., Cosstick, R. & Cech, T.R Synthesis and characterization of an RNA dinucleotide containing a 3'-S-phosphorothiolate linkage. J. Am. Chem. Soc. 118,10341-10350 (1996).
    • (1996) J. Am. Chem. Soc , vol.118 , pp. 10341-10350
    • Weinstein, L.B.1    Earnshaw, D.J.2    Cosstick, R.3    Cech, T.R.4
  • 7
    • 0030659506 scopus 로고    scopus 로고
    • Synthesis of 3'-thioribonucleosides and their incorporation into oligoribonucleotides via phosphoramidite chemistry
    • Sun, S.G., Yoshida, A. & Piccirilli, J.A. Synthesis of 3'-thioribonucleosides and their incorporation into oligoribonucleotides via phosphoramidite chemistry. RNA 3, 1352-1363 (1997).
    • (1997) RNA , vol.3 , pp. 1352-1363
    • Sun, S.G.1    Yoshida, A.2    Piccirilli, J.A.3
  • 8
    • 0032847294 scopus 로고    scopus 로고
    • Bridging sulfur substitutions in the analysis of pre-mRNA splicing
    • Sontheimer, E.J. Bridging sulfur substitutions in the analysis of pre-mRNA splicing. Methods 18, 29-37 (1999).
    • (1999) Methods , vol.18 , pp. 29-37
    • Sontheimer, E.J.1
  • 9
    • 0001413188 scopus 로고    scopus 로고
    • Functional evidence that the 3'-5' exonuclease domain of Escherichia coli DNA polymerase I employs a divalent metalion in leaving group stabilization
    • Curley, J.F., Joyce, C.M. & Piccirilli, J.A. Functional evidence that the 3'-5' exonuclease domain of Escherichia coli DNA polymerase I employs a divalent metalion in leaving group stabilization. J. Am. Chem. Soc. 119, 12691-12692 (1997).
    • (1997) J. Am. Chem. Soc. , vol.119 , pp. 12691-12692
    • Curley, J.F.1    Joyce, C.M.2    Piccirilli, J.A.3
  • 10
    • 0033547832 scopus 로고    scopus 로고
    • Structures of normal single- stranded DNA and deoxyribo-3'-S-phosphorothiolates bound to the 3'-5' exonucleolytic activesiteofDNApolymerasel from Escherichia coli
    • Brautigam, C.A., Sun, S., Piccirilli, J.A. & Steitz, T.A. Structures of normal single- stranded DNA and deoxyribo-3'-S-phosphorothiolates bound to the 3'-5' exonucleolytic activesiteofDNApolymerasel from Escherichia coli. Biochemistry 38, 696-704 (1999).
    • (1999) Biochemistry , vol.38 , pp. 696-704
    • Brautigam, C.A.1    Sun, S.2    Piccirilli, J.A.3    Steitz, T.A.4
  • 11
    • 0030936839 scopus 로고    scopus 로고
    • The RuvC protein dimer resolves Holliday junctions by a dual incision mechanism that involves base-specific contacts
    • Shah, R., Cosstick, R. & West, S.C. The RuvC protein dimer resolves Holliday junctions by a dual incision mechanism that involves base-specific contacts. EMBO J. 16, 1464-1472 (1997).
    • (1997) EMBO J , vol.16 , pp. 1464-1472
    • Shah, R.1    Cosstick, R.2    West, S.C.3
  • 12
    • 26244465679 scopus 로고    scopus 로고
    • Mechanism of the Escherichia coli DNA T: G-mismatch endonuclease (Vsr protein) thiophosphate- containing probed with oligodeoxynucleotides
    • Elliott, S.L., Brazier, J., Cosstick, R. & Connolly, B.A. Mechanism of the Escherichia coli DNA T: G-mismatch endonuclease (Vsr protein) thiophosphate- containing probed with oligodeoxynucleotides. J. Mol. Biol. 353, 692-703 (2005).
    • (2005) J. Mol. Biol , vol.353 , pp. 692-703
    • Elliott, S.L.1    Brazier, J.2    Cosstick, R.3    Connolly, B.A.4
  • 13
    • 0033228935 scopus 로고    scopus 로고
    • Conformational analysis of 3'-S-PO3-linked ribo- and deoxyribodinucleoside monophosphates
    • Beevers, A.P. et al. Conformational analysis of 3'-S-PO3-linked ribo- and deoxyribodinucleoside monophosphates. Magn. Reson. Chem. 37, 814-820 (1999).
    • (1999) Magn. Reson. Chem , vol.37 , pp. 814-820
    • Beevers, A.P.1
  • 14
    • 0036306871 scopus 로고    scopus 로고
    • Probing the effect of a 3'-S-phosphorothiolate link on the conformation ofa DNA: RNA hybrid; implications forantisense drug design
    • Beevers, A.P. et al. Probing the effect of a 3'-S-phosphorothiolate link on the conformation ofa DNA: RNA hybrid; implications forantisense drug design. Chem. Commun. (Camb.), 1458-1459 (2002).
    • (2002) Chem. Commun. (Camb.) , pp. 1458-1459
    • Beevers, A.P.1
  • 15
    • 29344445180 scopus 로고    scopus 로고
    • Stabilization of the DNA I-motif structure by incorporation of 3'-S-phosphorothiolate linkages
    • Brazier, J.A., Fisher, J. & Cosstick, R. Stabilization of the DNA I-motif structure by incorporation of 3'-S-phosphorothiolate linkages. Angew. Chem. Int. Ed. Engl. 45, 114-117 (2006).
    • (2006) Angew. Chem. Int. Ed. Engl , vol.45 , pp. 114-117
    • Brazier, J.A.1    Fisher, J.2    Cosstick, R.3
  • 16
    • 0026693178 scopus 로고
    • New methods for the synthesis of 3'-S- phosphorothiolate internucleoside linkages
    • Vyle, J.S., Li, X. & Cosstick, R. New methods for the synthesis of 3'-S- phosphorothiolate internucleoside linkages. Tetrahedron Lett. 33, 3017-3020 (1992).
    • (1992) Tetrahedron Lett , vol.33 , pp. 3017-3020
    • Vyle, J.S.1    Li, X.2    Cosstick, R.3
  • 17
    • 37049069030 scopus 로고
    • Application of the Michaelis-Arbuzov reaction to the synthesis of internucleoside 3'-S-phosphorothiolate linkages
    • Li, X. et al. Application of the Michaelis-Arbuzov reaction to the synthesis of internucleoside 3'-S-phosphorothiolate linkages. J. Chem. Soc., Perkin Trans. 1, 2123-2129 (1994).
    • (1994) J. Chem. Soc., Perkin Trans , vol.1 , pp. 2123-2129
    • Li, X.1
  • 18
    • 0024446964 scopus 로고
    • Solid-phase synthesis of oligonucleotides containing 3'-thiothymidine
    • Cosstick, R. & Vyle, J.S. Solid-phase synthesis of oligonucleotides containing 3'-thiothymidine. Tetrahedron Lett. 30, 4693-4696 (1989).
    • (1989) Tetrahedron Lett , vol.30 , pp. 4693-4696
    • Cosstick, R.1    Vyle, J.S.2
  • 19
    • 0025271245 scopus 로고
    • Synthesis and properties of dithymidine phosphate analogs containing 3'-thiothymidine
    • Cosstick, R. & Vyle, J.S. Synthesis and properties of dithymidine phosphate analogs containing 3'-thiothymidine. Nucleic Acids Res. 18, 829-835 (1990).
    • (1990) Nucleic Acids Res , vol.18 , pp. 829-835
    • Cosstick, R.1    Vyle, J.S.2
  • 20
    • 0030731865 scopus 로고    scopus 로고
    • Synthesis of3'-thioribouridine, 3'-thioribocytidine, and their phosphoramidites
    • Sun, S.G. & Piccirilli, J.A. Synthesis of3'-thioribouridine, 3'-thioribocytidine, and their phosphoramidites. Nucleosides Nucleotides 16, 1543-1545 (1997).
    • (1997) Nucleosides Nucleotides , vol.16 , pp. 1543-1545
    • Sun, S.G.1    Piccirilli, J.A.2
  • 21
    • 1342264715 scopus 로고    scopus 로고
    • Synthesis of phosphorothioamidites derived from 3'-thio-3'- deoxythymidine and 3'-thio- 2',3'-dideoxycytidine and the automated synthesis of oligodeoxynucleotides containing a 3'- S-phosphorothiolate linkage
    • Sabbagh, G., Fettes, K.J., Gosain, R., O'Neil, I.A. & Cosstick, R. Synthesis of phosphorothioamidites derived from 3'-thio-3'- deoxythymidine and 3'-thio- 2',3'-dideoxycytidine and the automated synthesis of oligodeoxynucleotides containing a 3'- S-phosphorothiolate linkage. Nucleic Acids Res. 32, 495-501 (2004).
    • (2004) Nucleic Acids Res , vol.32 , pp. 495-501
    • Sabbagh, G.1    Fettes, K.J.2    Gosain, R.3    O'neil, I.A.4    Cosstick, R.5
  • 22
    • 0026561950 scopus 로고
    • Synthesis of a dinucleoside 3'-S- phosphorothiolate containing 2'-deoxy-3'-thioadenosine
    • Li, X., Andrews, D.M. & Cosstick, R. Synthesis of a dinucleoside 3'-S- phosphorothiolate containing 2'-deoxy-3'-thioadenosine. Tetrahedron 48, 2729-2738 (1992).
    • (1992) Tetrahedron , vol.48 , pp. 2729-2738
    • Li, X.1    Rews, D.M.2    Cosstick, R.3
  • 23
    • 33947588791 scopus 로고    scopus 로고
    • 2',3'-Dideoxy-3'- thionucleoside triphosphates: Syntheses and polymerase substrate activities
    • Meena Sam, M., Pierce, K., Szostak, J.W. & McLaughlin, L.W. 2',3'-Dideoxy-3'- thionucleoside triphosphates: syntheses and polymerase substrate activities. Org. Lett. 9, 1161-1163 (2007).
    • (2007) Org. Lett , vol.9 , pp. 1161-1163
    • Meena Sam, M.1    Pierce, K.2    Szostak, J.W.3    McLaughlin, L.W.4
  • 24
    • 33644546677 scopus 로고    scopus 로고
    • Synthesis and characterization of a [3-N-15]-labeled cis-syn thymine dimer-containing DNA duplex
    • Bdour, H.M., Kao, J.L.F. & Taylor, J.S. Synthesis and characterization of a [3-N-15]-labeled cis-syn thymine dimer-containing DNA duplex. J. Org. Chem. 71, 1640-1646 (2006).
    • (2006) J. Org. Chem , vol.71 , pp. 1640-1646
    • Bdour, H.M.1    Kao, J.L.F.2    Taylor, J.S.3
  • 26
    • 33947483704 scopus 로고
    • Studies on polynucleotides.24. Stepwise synthesis of specific deoxyribopolynucleotides (4)—protected derivatives of deoxyribonucleosidesand new syntheses ofdeoxyribonucleoside-3- phosphates
    • Schaller, H., Weimann, G., Khorana, H.G. & Lerch, B. Studies on polynucleotides.24. Stepwise synthesis of specific deoxyribopolynucleotides (4)—protected derivatives of deoxyribonucleosidesand new syntheses ofdeoxyribonucleoside-3- phosphates. J. Am. Chem. Soc. 85, 3821-3827 (1963).
    • (1963) J. Am. Chem. Soc , vol.85 , pp. 3821-3827
    • Schaller, H.1    Weimann, G.2    Khorana, H.G.3    Lerch, B.4
  • 27
    • 0013619530 scopus 로고
    • The organic chemistry underlying DNA synthesis
    • Sonveaux, E. The organic chemistry underlying DNA synthesis. Bioorg. Chem. 14, 274-325 (1986).
    • (1986) Bioorg. Chem , vol.14 , pp. 274-325
    • Sonveaux, E.1
  • 28
    • 33947199663 scopus 로고    scopus 로고
    • Exploring the synthesis of masked phosphoramido 6-vinylcytidine derivatives as building blocks for cross-linking oligonucleotides
    • Radi, M., Spinosa, R., Parlato, M.C., Corelli, F. & Botta, M. Exploring the synthesis of masked phosphoramido 6-vinylcytidine derivatives as building blocks for cross-linking oligonucleotides. Heterocycles 69, 151-166 (2006).
    • (2006) Heterocycles , vol.69 , pp. 151-166
    • Radi, M.1    Spinosa, R.2    Parlato, M.C.3    Corelli, F.4    Botta, M.5
  • 29
    • 0001518039 scopus 로고
    • Transient protection—efficient one-flask syntheses of protected deoxynucleosides
    • Ti, G.S., Gaffney, B.L. & Jones, R.A. Transient protection—efficient one-flask syntheses of protected deoxynucleosides. J. Am. Chem. Soc. 104,1316-1319 (1982).
    • (1982) J. Am. Chem. Soc , vol.104 , pp. 1316-1319
    • Ti, G.S.1    Gaffney, B.L.2    Jones, R.A.3
  • 30
    • 34548180906 scopus 로고    scopus 로고
    • Practical Proline-catalyzed asymmetric Mannich reaction of aldehydes with N-Boc-imines
    • Yang, J.W., Stadler, M. & List, B. Practical Proline-catalyzed asymmetric Mannich reaction of aldehydes with N-Boc-imines. Nat. Protoc. 2, 1937-1942 (2007).
    • (2007) Nat. Protoc , vol.2 , pp. 1937-1942
    • Yang, J.W.1    Stadler, M.2    List, B.3
  • 31
    • 35648975272 scopus 로고    scopus 로고
    • Duplex stability ofDNA.DNAand DNA.RNA duplexes containing 3'-S-phosphorothiolate linkages
    • Bentley, J., Brazier, J.A., Fisher, J. & Cosstick, R. Duplex stability ofDNA.DNAand DNA.RNA duplexes containing 3'-S-phosphorothiolate linkages. Org. Biomol. Chem. 5, 3698-3702 (2007).
    • (2007) Org. Biomol. Chem , vol.5 , pp. 3698-3702
    • Bentley, J.1    Brazier, J.A.2    Fisher, J.3    Cosstick, R.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.