메뉴 건너뛰기




Volumn 19, Issue 8, 2008, Pages 1726-1734

Utilization of intrachain 4′-C-azidomethylthymidine for preparation of oligodeoxyribonucleotide conjugates by click chemistry in solution and on a solid support

Author keywords

[No Author keywords available]

Indexed keywords

DNA; IONIC STRENGTH; MONOMERS; RNA; SOLID SOLUTIONS; SYNTHESIS (CHEMICAL);

EID: 50249162535     PISSN: 10431802     EISSN: None     Source Type: Journal    
DOI: 10.1021/bc800221p     Document Type: Article
Times cited : (66)

References (56)
  • 1
    • 33751401266 scopus 로고    scopus 로고
    • Application of unnatural oligonucleotides to chemical modification of gene expression
    • Sasaki, S., and Nagatsuki, F. (2006) Application of unnatural oligonucleotides to chemical modification of gene expression. Curr. Opin. Chem. Biol. 10, 615-621.
    • (2006) Curr. Opin. Chem. Biol , vol.10 , pp. 615-621
    • Sasaki, S.1    Nagatsuki, F.2
  • 2
    • 23844543479 scopus 로고    scopus 로고
    • Antisense oligonucleotides: The state of the art
    • Aboul-Fadl, T. (2005) Antisense oligonucleotides: The state of the art. Curr. Med. Chem. 12, 2193-2214.
    • (2005) Curr. Med. Chem , vol.12 , pp. 2193-2214
    • Aboul-Fadl, T.1
  • 3
    • 1542269161 scopus 로고    scopus 로고
    • Progress in antisense technology
    • Crooke, S. T. (2004) Progress in antisense technology. Annu. Rev. Med. 55, 61-95.
    • (2004) Annu. Rev. Med , vol.55 , pp. 61-95
    • Crooke, S.T.1
  • 4
    • 11944267365 scopus 로고
    • Antisense oligonucleotides: A new therapeutic principle
    • Uhlmann, E., and Peyman, A. (1990) Antisense oligonucleotides: a new therapeutic principle. Chem. Rev. 90, 543-584.
    • (1990) Chem. Rev , vol.90 , pp. 543-584
    • Uhlmann, E.1    Peyman, A.2
  • 5
    • 38549157506 scopus 로고    scopus 로고
    • Molecular biology: The expanding world of small RNAs
    • Grosshans, H., and Filipowicz, W. (2008) Molecular biology: The expanding world of small RNAs. Nature 451, 414-416.
    • (2008) Nature , vol.451 , pp. 414-416
    • Grosshans, H.1    Filipowicz, W.2
  • 6
    • 33845780974 scopus 로고    scopus 로고
    • RNA learns from antisense
    • Corey, D. R. (2007) RNA learns from antisense. Nat. Chem. Biol. 3, 8-11.
    • (2007) Nat. Chem. Biol , vol.3 , pp. 8-11
    • Corey, D.R.1
  • 7
    • 1942499451 scopus 로고    scopus 로고
    • Improving the efficiency of RNA interference in mammals
    • Mittal, V. (2004) Improving the efficiency of RNA interference in mammals. Nat. Rev. Genet. 5, 355-365.
    • (2004) Nat. Rev. Genet , vol.5 , pp. 355-365
    • Mittal, V.1
  • 8
    • 33751430435 scopus 로고    scopus 로고
    • Building oligonucleotide therapeutics using non-natural chemistries
    • Wilson, C., and Keefe, A. D. (2006) Building oligonucleotide therapeutics using non-natural chemistries. Curr. Opin. Chem. Biol. 10, 607-614.
    • (2006) Curr. Opin. Chem. Biol , vol.10 , pp. 607-614
    • Wilson, C.1    Keefe, A.D.2
  • 9
    • 33847036990 scopus 로고    scopus 로고
    • Strategies for silencing human disease using RNA interference
    • Kim, D. H., and Rossi, J. J. (2007) Strategies for silencing human disease using RNA interference. Nat. Rev. Genet. 8, 173-184.
    • (2007) Nat. Rev. Genet , vol.8 , pp. 173-184
    • Kim, D.H.1    Rossi, J.J.2
  • 10
    • 33751099034 scopus 로고    scopus 로고
    • RNAi therapeutics: A potential new class of pharmaceutical drugs
    • Bumcrot, D., Manoharan, M., Koteliansky, V., and Sah, D. W. Y. (2006) RNAi therapeutics: a potential new class of pharmaceutical drugs. Nat. Chem. Biol. 2, 711-719.
    • (2006) Nat. Chem. Biol , vol.2 , pp. 711-719
    • Bumcrot, D.1    Manoharan, M.2    Koteliansky, V.3    Sah, D.W.Y.4
  • 11
    • 33645148088 scopus 로고    scopus 로고
    • The silent treatment: SiRNAs as small molecule drugs
    • Dykxhoorn, D. M., Palliser, D., and Lieberman, J. (2006) The silent treatment: siRNAs as small molecule drugs. Gene Ther. 13, 541-552.
    • (2006) Gene Ther , vol.13 , pp. 541-552
    • Dykxhoorn, D.M.1    Palliser, D.2    Lieberman, J.3
  • 12
    • 21344457432 scopus 로고    scopus 로고
    • RNA interference: From gene silencing to gene-specific therapeutics
    • Leung, R. K. M., and Whittaker, P. A. (2005) RNA interference: from gene silencing to gene-specific therapeutics. Pharm. Ther. 107, 222-239.
    • (2005) Pharm. Ther , vol.107 , pp. 222-239
    • Leung, R.K.M.1    Whittaker, P.A.2
  • 13
    • 3242677639 scopus 로고    scopus 로고
    • siRNA: Applications in functional genomics and potential as therapeutics
    • Dorsett, Y., and Tuschl, T. (2004) siRNA: applications in functional genomics and potential as therapeutics. Nat. Rev. Drug Discovery 3, 318-329.
    • (2004) Nat. Rev. Drug Discovery , vol.3 , pp. 318-329
    • Dorsett, Y.1    Tuschl, T.2
  • 14
    • 0035989886 scopus 로고    scopus 로고
    • Oligonucleotide conjugates as potential antisense drugs with improved uptake, biodistribution, targeted delivery, and mechanism of action
    • Manoharan, M. (2002) Oligonucleotide conjugates as potential antisense drugs with improved uptake, biodistribution, targeted delivery, and mechanism of action. Antisense Nucleic Acids Drug Dev. 12, 103-108.
    • (2002) Antisense Nucleic Acids Drug Dev , vol.12 , pp. 103-108
    • Manoharan, M.1
  • 16
    • 0037600638 scopus 로고    scopus 로고
    • Peptide-mediated cellular delivery of antisense oligonucleotides and their analogues
    • Gait, M. J. (2003) Peptide-mediated cellular delivery of antisense oligonucleotides and their analogues. Cell. Mol. Life Sci. 60, 844-853.
    • (2003) Cell. Mol. Life Sci , vol.60 , pp. 844-853
    • Gait, M.J.1
  • 17
    • 33749823347 scopus 로고    scopus 로고
    • Peptide conjugates of oligonucleotides: Synthesis and applications
    • Venkatesan, N., and Kim, B. H. (2006) Peptide conjugates of oligonucleotides: synthesis and applications. Chem. Rev. 106, 3712-3761.
    • (2006) Chem. Rev , vol.106 , pp. 3712-3761
    • Venkatesan, N.1    Kim, B.H.2
  • 20
    • 38949186041 scopus 로고    scopus 로고
    • Site-specific delivery of oligonucleotides to hapatocytes after systemic administration
    • Zhu, L., Ye, Z., Cheng, K., Miller, D. D., and Mahoto, R. I. (2008) Site-specific delivery of oligonucleotides to hapatocytes after systemic administration. Bioconjugate Chem. 19, 290-298.
    • (2008) Bioconjugate Chem , vol.19 , pp. 290-298
    • Zhu, L.1    Ye, Z.2    Cheng, K.3    Miller, D.D.4    Mahoto, R.I.5
  • 22
    • 13644254495 scopus 로고    scopus 로고
    • Lactosylated poly(ethylene glycol)-siRNA conjugate through acid-labile β-thiopropionate linkage to construct pH-sensitive polyion complex micelles achieving enhanced gene silencing in hepatoma cells
    • Oishi, M., Nagasaki, Y., Itaka, K., Nishiyama, N., and Kataoka, K (2005) Lactosylated poly(ethylene glycol)-siRNA conjugate through acid-labile β-thiopropionate linkage to construct pH-sensitive polyion complex micelles achieving enhanced gene silencing in hepatoma cells. J. Am. Chem. Soc. 127, 1624-1625.
    • (2005) J. Am. Chem. Soc , vol.127 , pp. 1624-1625
    • Oishi, M.1    Nagasaki, Y.2    Itaka, K.3    Nishiyama, N.4    Kataoka, K.5
  • 23
    • 33847642135 scopus 로고    scopus 로고
    • Glycotargeting to improve cellular delivery efficiency of nucleic acids
    • Yan, H., and Tram, K. (2007) Glycotargeting to improve cellular delivery efficiency of nucleic acids. Glycoconj. J. 24, 107-123.
    • (2007) Glycoconj. J , vol.24 , pp. 107-123
    • Yan, H.1    Tram, K.2
  • 24
    • 18844424653 scopus 로고    scopus 로고
    • Lectins: Tools for the molecular understanding of the glycocode
    • Ambrosi, M., Cameron, N. R., and Davis, B. G. (2005) Lectins: tools for the molecular understanding of the glycocode. Org. Biomol. Chem. 3, 1593-1608.
    • (2005) Org. Biomol. Chem , vol.3 , pp. 1593-1608
    • Ambrosi, M.1    Cameron, N.R.2    Davis, B.G.3
  • 25
    • 0036462602 scopus 로고    scopus 로고
    • The cluster glycoside effect
    • Lundquist, J. J., and Toone, E. J. (2002) The cluster glycoside effect. Chem. Rev. 102, 555-578.
    • (2002) Chem. Rev , vol.102 , pp. 555-578
    • Lundquist, J.J.1    Toone, E.J.2
  • 26
    • 0037804209 scopus 로고    scopus 로고
    • N- Methylpiperazinocarbonyl-2′,3′-BcNA and 4′-C-(N- methylpiperazino)m-ethyl-DNA: Introduction of basic functionalities facing the major groove and the minor groove of a DNA:DNA duplex
    • Raunkjaer, M., Bryld, T., and Wengel, J. (2003) N- Methylpiperazinocarbonyl-2′,3′-BcNA and 4′-C-(N- methylpiperazino)m-ethyl-DNA: introduction of basic functionalities facing the major groove and the minor groove of a DNA:DNA duplex. Chem. Commun. 1604-1605.
    • (2003) Chem. Commun , pp. 1604-1605
    • Raunkjaer, M.1    Bryld, T.2    Wengel, J.3
  • 27
    • 0032909507 scopus 로고    scopus 로고
    • Synthesis of 3′-C- and 4′-C-branched oligodeoxynucleotides and the development of locked nucleic acid (LNA)
    • Wengel, J. (1999) Synthesis of 3′-C- and 4′-C-branched oligodeoxynucleotides and the development of locked nucleic acid (LNA). Acc. Chem. Res. 32, 301-310.
    • (1999) Acc. Chem. Res , vol.32 , pp. 301-310
    • Wengel, J.1
  • 28
    • 0033966034 scopus 로고    scopus 로고
    • Oligonucleotides containing novel 4′-C- or 3′-C- (aminoalkyl)-branched thymidines
    • Pfundheller, H. M., Bryld, T., Olsen, C. E., and Wengel, J. (2000) Oligonucleotides containing novel 4′-C- or 3′-C- (aminoalkyl)-branched thymidines. Helv. Chim. Acta 83, 128-151.
    • (2000) Helv. Chim. Acta , vol.83 , pp. 128-151
    • Pfundheller, H.M.1    Bryld, T.2    Olsen, C.E.3    Wengel, J.4
  • 29
    • 0001191968 scopus 로고    scopus 로고
    • Nucleosides and nucleotides. 174. Synthesis of oligodeoxynucleotides containing 4′-C-[2[[N-(2-aminoethyl) carbamoyl]oxy]ethyl]thymidine and their thermal stability and nuclease-resistance properties
    • Ueno, Y., Nagasawa, Y., Sugimoto, I., Kojima, N., Kanazaki, M., Shuto, S., and Matsuda, A. (1998) Nucleosides and nucleotides. 174. Synthesis of oligodeoxynucleotides containing 4′-C-[2[[N-(2-aminoethyl) carbamoyl]oxy]ethyl]thymidine and their thermal stability and nuclease-resistance properties. J. Org. Chem 63, 1660-1667.
    • (1998) J. Org. Chem , vol.63 , pp. 1660-1667
    • Ueno, Y.1    Nagasawa, Y.2    Sugimoto, I.3    Kojima, N.4    Kanazaki, M.5    Shuto, S.6    Matsuda, A.7
  • 30
    • 0030565529 scopus 로고    scopus 로고
    • Synthesis and evaluation of oligodeoxynucleotides containing 4′-C-substituted thymidines
    • Wang, G., and Seifert, W. E. (1996) Synthesis and evaluation of oligodeoxynucleotides containing 4′-C-substituted thymidines. Tetrahedron Lett. 37, 6515-6518.
    • (1996) Tetrahedron Lett , vol.37 , pp. 6515-6518
    • Wang, G.1    Seifert, W.E.2
  • 31
    • 0028909471 scopus 로고
    • Synthesis of oligodeoxynucleotides containing 4′-C-(hydroxymethyl)thymidine: Novel promising antisense molecules
    • Fensholdt, J., Thrane, H., and Wengel, J. (1995) Synthesis of oligodeoxynucleotides containing 4′-C-(hydroxymethyl)thymidine: Novel promising antisense molecules. Tetrahedron Lett. 36, 2535-2538.
    • (1995) Tetrahedron Lett , vol.36 , pp. 2535-2538
    • Fensholdt, J.1    Thrane, H.2    Wengel, J.3
  • 32
    • 0029148176 scopus 로고
    • Novel linear and branched oligodeoxynucleotide analogues containing 4′-C- (hydroxymethyl)thymidine
    • Thrane, H., Fensholdt, J., Regner, M., and Wengel, J. (1995) Novel linear and branched oligodeoxynucleotide analogues containing 4′-C- (hydroxymethyl)thymidine. Tetrahedron 51, 10389-10402.
    • (1995) Tetrahedron , vol.51 , pp. 10389-10402
    • Thrane, H.1    Fensholdt, J.2    Regner, M.3    Wengel, J.4
  • 33
    • 0027967502 scopus 로고
    • Oligodeoxynucleotide probes with multiple labels linked to the 4′-position of thymidine monomers: Excellent duplex stability and detection sensitivity
    • Maag, H., Schmidt, B., and Rose, S. J. (1994) Oligodeoxynucleotide probes with multiple labels linked to the 4′-position of thymidine monomers: Excellent duplex stability and detection sensitivity. Tetrahedron Lett. 35, 6449-6452.
    • (1994) Tetrahedron Lett , vol.35 , pp. 6449-6452
    • Maag, H.1    Schmidt, B.2    Rose, S.J.3
  • 34
    • 0037099395 scopus 로고    scopus 로고
    • A stepwise Huisgen cycloaddition process: Copper(I)-catalyzed regioselective "ligation" of azides and terminal alkynes
    • Rostovtsev, V. V., Green, L. G., Fokin, V. V., and Sharpless, K. B. (2002) A stepwise Huisgen cycloaddition process: Copper(I)-catalyzed regioselective "ligation" of azides and terminal alkynes. Angew. Chem., Int. Ed. 41, 2596-2599.
    • (2002) Angew. Chem., Int. Ed , vol.41 , pp. 2596-2599
    • Rostovtsev, V.V.1    Green, L.G.2    Fokin, V.V.3    Sharpless, K.B.4
  • 35
    • 0037012920 scopus 로고    scopus 로고
    • Peptidotriazoles on solid phase: [1,2,3]-triazoles by regiospecific copper(I)-catalyzed 1,3-dipolar cycloadditions of terminal alkynes to azides
    • Tornoe, C. W., Christensen, C., and Meldal, M. (2002) Peptidotriazoles on solid phase: [1,2,3]-triazoles by regiospecific copper(I)-catalyzed 1,3-dipolar cycloadditions of terminal alkynes to azides. J. Org. Chem. 67, 3057-3064.
    • (2002) J. Org. Chem , vol.67 , pp. 3057-3064
    • Tornoe, C.W.1    Christensen, C.2    Meldal, M.3
  • 36
    • 33748609388 scopus 로고    scopus 로고
    • Click chemistry as a reliable method for the high-density postsynthetic functionalization of alkyne-modified DNA
    • Gierlich, J., Burley, G. A., Gramlich, P. M. E., Hammond, D. M., and Carell, T. (2006) Click chemistry as a reliable method for the high-density postsynthetic functionalization of alkyne-modified DNA. Org. Lett. 8, 3639-3642.
    • (2006) Org. Lett , vol.8 , pp. 3639-3642
    • Gierlich, J.1    Burley, G.A.2    Gramlich, P.M.E.3    Hammond, D.M.4    Carell, T.5
  • 37
    • 34249794857 scopus 로고    scopus 로고
    • Template-directed oligonucleotide strand ligation, covalent intramolecular DNA circularization and catenation using click chemistry
    • Kumar, R., El-Sagheer, A., Tumpane, J., Lincoln, P., Wilhelmsson, L. M., and Brown, T. (2007) Template-directed oligonucleotide strand ligation, covalent intramolecular DNA circularization and catenation using click chemistry. J. Am. Chem. Soc. 129, 6859-6864.
    • (2007) J. Am. Chem. Soc , vol.129 , pp. 6859-6864
    • Kumar, R.1    El-Sagheer, A.2    Tumpane, J.3    Lincoln, P.4    Wilhelmsson, L.M.5    Brown, T.6
  • 38
    • 34250023096 scopus 로고    scopus 로고
    • Nucleosides and oligonucleotides with diynyl side chains: Base pairing and functionalization of 2′-deoxyuridine derivatives by the copper(I)-catalyzed alkyne-azide 'click'cycloaddition
    • Seela, F., and Sirivolu, V. R. (2007) Nucleosides and oligonucleotides with diynyl side chains: base pairing and functionalization of 2′-deoxyuridine derivatives by the copper(I)-catalyzed alkyne-azide 'click'cycloaddition. Helv. Chim. Acta 90, 535-552.
    • (2007) Helv. Chim. Acta , vol.90 , pp. 535-552
    • Seela, F.1    Sirivolu, V.R.2
  • 41
    • 15044352655 scopus 로고    scopus 로고
    • Conversion of DNA methyltransferases into azidonucleosidyl transferases via synthetic cofactors
    • Comstock, L. R., and Rajski, S. R. (2005) Conversion of DNA methyltransferases into azidonucleosidyl transferases via synthetic cofactors. Nucleic Acids Res. 33, 1644-1652.
    • (2005) Nucleic Acids Res , vol.33 , pp. 1644-1652
    • Comstock, L.R.1    Rajski, S.R.2
  • 42
    • 26844534670 scopus 로고    scopus 로고
    • Methyltransferase-directed DNA strand scission
    • Comstock, L. R., and Rajski, S. R. (2005) Methyltransferase-directed DNA strand scission. J. Am. Chem. Soc. 127, 14136-14137.
    • (2005) J. Am. Chem. Soc , vol.127 , pp. 14136-14137
    • Comstock, L.R.1    Rajski, S.R.2
  • 43
    • 34248203825 scopus 로고    scopus 로고
    • A nucleoside triphosphate for site-specific labelling of DNA by the Staudinger ligation
    • Weisbrod, S. H., and Marx, A. (2007) A nucleoside triphosphate for site-specific labelling of DNA by the Staudinger ligation. Chem. Commun. 1828-1830.
    • (2007) Chem. Commun , pp. 1828-1830
    • Weisbrod, S.H.1    Marx, A.2
  • 44
    • 34447527472 scopus 로고    scopus 로고
    • DNA conjugation by the Staudinger ligation: New thymidine analogues
    • Baccaro, A., Weisbrod, S. H., and Marx, A. (2007) DNA conjugation by the Staudinger ligation: New thymidine analogues. Synthesis 1949-1945.
    • (2007) Synthesis , pp. 1949-1945
    • Baccaro, A.1    Weisbrod, S.H.2    Marx, A.3
  • 45
    • 0035945004 scopus 로고    scopus 로고
    • Synthesis and properties of 2-azidodeoxyadenosine and its incorporation into oligodeoxynucleotides
    • Wada, T., Mochizuki, A., Higashiya, S., Tsuruoka, H., Kawahara, S., Ishikawa, M., and Sekine, M. (2001) Synthesis and properties of 2-azidodeoxyadenosine and its incorporation into oligodeoxynucleotides. Tetrahedron Lett. 42, 9215-9219.
    • (2001) Tetrahedron Lett , vol.42 , pp. 9215-9219
    • Wada, T.1    Mochizuki, A.2    Higashiya, S.3    Tsuruoka, H.4    Kawahara, S.5    Ishikawa, M.6    Sekine, M.7
  • 46
    • 0000096953 scopus 로고
    • Nucleoside H-phosphonates. III. Chemical synthesis of oligodeoxyribonucleotides by the hydrogenphosphonate approach
    • Garegg, P. J., Lindh, I., Regberg, T., Stawinski, J., and Strömberg, R. (1986) Nucleoside H-phosphonates. III. Chemical synthesis of oligodeoxyribonucleotides by the hydrogenphosphonate approach. Tetrahedron Lett. 27, 4051-4054.
    • (1986) Tetrahedron Lett , vol.27 , pp. 4051-4054
    • Garegg, P.J.1    Lindh, I.2    Regberg, T.3    Stawinski, J.4    Strömberg, R.5
  • 47
    • 0000096954 scopus 로고
    • Nucleoside H-phosphonates. IV. Automated solid-phase synthesis of oligodeoxyribonucleotides by the hydrogenphosphonate approach
    • Garegg, P. J., Lindh, I., Regberg, T., Stawinski, J., and Strömberg, R. (1986) Nucleoside H-phosphonates. IV. Automated solid-phase synthesis of oligodeoxyribonucleotides by the hydrogenphosphonate approach. Tetrahedron Lett. 27, 4055-4058.
    • (1986) Tetrahedron Lett , vol.27 , pp. 4055-4058
    • Garegg, P.J.1    Lindh, I.2    Regberg, T.3    Stawinski, J.4    Strömberg, R.5
  • 49
    • 33845559837 scopus 로고
    • 4′-Substituted nucleosides. 5. Hydroxymethylation of nucleoside 5′-aldehydes
    • Jones, G. H., Taniguchi, M., Tegg, D., and Moffatt, J. G. (1979) 4′-Substituted nucleosides. 5. Hydroxymethylation of nucleoside 5′-aldehydes. J. Org. Chem. 44, 1309-1317.
    • (1979) J. Org. Chem , vol.44 , pp. 1309-1317
    • Jones, G.H.1    Taniguchi, M.2    Tegg, D.3    Moffatt, J.G.4
  • 50
    • 42049099500 scopus 로고    scopus 로고
    • Synthesis of 4′-C-modified 2′-deoxyribonucleoside analogues and oligonucleotides
    • Jung, K.-H., and Marx, A. (2008) Synthesis of 4′-C-modified 2′-deoxyribonucleoside analogues and oligonucleotides. Curr. Org. Chem. 12, 343-354.
    • (2008) Curr. Org. Chem , vol.12 , pp. 343-354
    • Jung, K.-H.1    Marx, A.2
  • 52
    • 0036206811 scopus 로고    scopus 로고
    • New modified single chained glycolipids. Part 1: Synthesis of deoxy and partially O-methylated glycolipids with or without a sulfur containing spacer
    • Schmidt, M., Chatterjee, S. K., Dobner, B., and Nuhn, P. (2002) New modified single chained glycolipids. Part 1: synthesis of deoxy and partially O-methylated glycolipids with or without a sulfur containing spacer. Chem. Phys. Lip. 114, 139-147.
    • (2002) Chem. Phys. Lip , vol.114 , pp. 139-147
    • Schmidt, M.1    Chatterjee, S.K.2    Dobner, B.3    Nuhn, P.4
  • 53
    • 0029905917 scopus 로고    scopus 로고
    • Rapid combinatorial synthesis of aminoglycoside antibiotic mimetics: Use of a polyethylene glycol-linked amine and a neamine-derived aldehyde in multiple component condensation as a strategy for the discovery of new inhibitors of the HIV RNA rev response element
    • Park, W. K. C., Auer, M., Jaksche, H., and Wong, C.-H. (1996) Rapid combinatorial synthesis of aminoglycoside antibiotic mimetics: Use of a polyethylene glycol-linked amine and a neamine-derived aldehyde in multiple component condensation as a strategy for the discovery of new inhibitors of the HIV RNA rev response element. J. Am. Chem. Soc. 118, 10150-10155.
    • (1996) J. Am. Chem. Soc , vol.118 , pp. 10150-10155
    • Park, W.K.C.1    Auer, M.2    Jaksche, H.3    Wong, C.-H.4
  • 54
    • 4444324951 scopus 로고    scopus 로고
    • Polytriazoles as copper(I)-stabilizing ligands in catalysis
    • Chan, T. R., Hilgraf, R., Sharpless, K. B., and Fokin, V. V. (2004) Polytriazoles as copper(I)-stabilizing ligands in catalysis. Org. Lett. 6, 2853-2855.
    • (2004) Org. Lett , vol.6 , pp. 2853-2855
    • Chan, T.R.1    Hilgraf, R.2    Sharpless, K.B.3    Fokin, V.V.4
  • 56
    • 0036408261 scopus 로고    scopus 로고
    • DNA minor groove hydration probed with 4′-alkylated thymidines
    • Detmer, I., Summerer, D., and Marx, A. (2002) DNA minor groove hydration probed with 4′-alkylated thymidines. Chem. Commun. 2314-2315.
    • (2002) Chem. Commun , pp. 2314-2315
    • Detmer, I.1    Summerer, D.2    Marx, A.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.