메뉴 건너뛰기




Volumn 42, Issue 22, 2014, Pages 13456-13468

Synthesis, biophysical properties and biological activity of second generation antisense oligonucleotides containing chiral phosphorothioate linkages

Author keywords

[No Author keywords available]

Indexed keywords

ANTISENSE OLIGONUCLEOTIDE; ANTISENSE OLIGONUCLEOTIDE 1; ANTISENSE OLIGONUCLEOTIDE 10; ANTISENSE OLIGONUCLEOTIDE 11; ANTISENSE OLIGONUCLEOTIDE 12; ANTISENSE OLIGONUCLEOTIDE 13; ANTISENSE OLIGONUCLEOTIDE 14; ANTISENSE OLIGONUCLEOTIDE 15; ANTISENSE OLIGONUCLEOTIDE 16; ANTISENSE OLIGONUCLEOTIDE 2; ANTISENSE OLIGONUCLEOTIDE 3; ANTISENSE OLIGONUCLEOTIDE 4; ANTISENSE OLIGONUCLEOTIDE 5; ANTISENSE OLIGONUCLEOTIDE 6; ANTISENSE OLIGONUCLEOTIDE 7; ANTISENSE OLIGONUCLEOTIDE 8; ANTISENSE OLIGONUCLEOTIDE 9; PHOSPHOROTHIOIC ACID; RIBONUCLEASE H; UNCLASSIFIED DRUG; ENDONUCLEASE S1, ASPERGILLUS; FUNGAL PROTEIN; NUCLEASE S1; OLIGONUCLEOTIDE PHOSPHOROTHIOATE;

EID: 84924538557     PISSN: 03051048     EISSN: 13624962     Source Type: Journal    
DOI: 10.1093/nar/gku1115     Document Type: Article
Times cited : (99)

References (53)
  • 1
    • 77949512140 scopus 로고    scopus 로고
    • RNA targeting therapeutics: Molecular mechanisms of antisense oligonucleotides as a therapeutic platform
    • Swayze, E. E. and Bennett, C. F. (2010) RNA targeting therapeutics: molecular mechanisms of antisense oligonucleotides as a therapeutic platform. Annu. Rev. Pharmacol. Toxicol., 50, 259-293.
    • (2010) Annu. Rev. Pharmacol. Toxicol. , vol.50 , pp. 259-293
    • Swayze, E.E.1    Bennett, C.F.2
  • 3
    • 0034015113 scopus 로고    scopus 로고
    • Phosphorothioate oligodeoxynucleotides: What is their origin and what is unique about them?
    • Eckstein, F. (2000) Phosphorothioate oligodeoxynucleotides:What is their origin and what is unique about them? Antisense Nucleic Acid Drug Dev., 10, 117-121.
    • (2000) Antisense Nucleic Acid Drug Dev. , vol.10 , pp. 117-121
    • Eckstein, F.1
  • 4
    • 0020479127 scopus 로고
    • Effect of deoxynucleoside phosphorothioates incorporated in DNA on cleavage by restriction enzymes
    • Vosberg, H. P. and Eckstein, F. (1982) Effect of deoxynucleoside phosphorothioates incorporated in DNA on cleavage by restriction enzymes. J. Biol. Chem., 257, 6595-6599.
    • (1982) J. Biol. Chem. , vol.257 , pp. 6595-6599
    • Vosberg, H.P.1    Eckstein, F.2
  • 5
    • 0035043324 scopus 로고    scopus 로고
    • Pharmacokinetics of phosphorothioate antisense oligodeoxynucleotides
    • Geary, R. S., Yu, R. Z. and Levin, A. A. (2001) Pharmacokinetics of phosphorothioate antisense oligodeoxynucleotides. Curr. Opin. Investig. Drugs, 2, 562-573.
    • (2001) Curr. Opin. Investig. Drugs , vol.2 , pp. 562-573
    • Geary, R.S.1    Yu, R.Z.2    Levin, A.A.3
  • 8
    • 61349102407 scopus 로고    scopus 로고
    • Ribonuclease H: The enzymes in eukaryotes
    • Cerritelli, S. M. and Crouch, R. J. (2009) Ribonuclease H: the enzymes in eukaryotes. FEBS J., 276, 1494-1505.
    • (2009) FEBS J. , vol.276 , pp. 1494-1505
    • Cerritelli, S.M.1    Crouch, R.J.2
  • 9
    • 2342427578 scopus 로고    scopus 로고
    • Determination of the role of the human RNase H1 in the pharmacology of DNA-like antisense drugs
    • Wu, H., Lima, W. F., Zhang, H., Fan, A., Sun, H. and Crooke, S. T. (2004) Determination of the role of the human RNase H1 in the pharmacology of DNA-like antisense drugs. J. Biol. Chem., 279, 17181-17189.
    • (2004) J. Biol. Chem. , vol.279 , pp. 17181-17189
    • Wu, H.1    Lima, W.F.2    Zhang, H.3    Fan, A.4    Sun, H.5    Crooke, S.T.6
  • 10
  • 11
    • 0022418143 scopus 로고
    • Bond order and charge localization in nucleoside phosphorothioates
    • Frey, P. A. and Sammons, R. D. (1985) Bond order and charge localization in nucleoside phosphorothioates. Science, 228, 541-545.
    • (1985) Science , vol.228 , pp. 541-545
    • Frey, P.A.1    Sammons, R.D.2
  • 13
    • 0029594158 scopus 로고
    • Stereodifferentiation - The effect of P chirality of oligo (nucleoside phosphorothioates) on the activity of bacterial RNase H
    • Koziolkiewicz, M., Krakowlak, A., Kwinkowski, M., Boczkowska, M. and Stec, W. J. (1995) Stereodifferentiation - the effect of P chirality of oligo (nucleoside phosphorothioates) on the activity of bacterial RNase H. Nucleic Acids Res., 23, 5000-5005.
    • (1995) Nucleic Acids Res. , vol.23 , pp. 5000-5005
    • Koziolkiewicz, M.1    Krakowlak, A.2    Kwinkowski, M.3    Boczkowska, M.4    Stec, W.J.5
  • 15
    • 0029071029 scopus 로고
    • Enzymatic synthesis of stereoregular (all Rp) oligonucleotide phosphorothioate and its properties
    • Tang, J., Roskey, A., Li, Y. and Agrawal, S. (1995) Enzymatic synthesis of stereoregular (all Rp) oligonucleotide phosphorothioate and its properties. Nucleosides Nucleotides, 14, 985-990.
    • (1995) Nucleosides Nucleotides , vol.14 , pp. 985-990
    • Tang, J.1    Roskey, A.2    Li, Y.3    Agrawal, S.4
  • 16
    • 33748216395 scopus 로고
    • Stereocontrolled synthesis of oligo (nucleoside phosphorothioate) s
    • Stec, W. J. and Wilk, A. (1994) Stereocontrolled synthesis of oligo (nucleoside phosphorothioate) s. Angew. Chem. Int. Ed., 33, 709-722.
    • (1994) Angew. Chem. Int. Ed. , vol.33 , pp. 709-722
    • Stec, W.J.1    Wilk, A.2
  • 17
    • 0034004337 scopus 로고    scopus 로고
    • Stereo-enriched phosphorothioate oligodeoxynucleotides: Synthesis, biophysical and biological properties
    • Yu, D., Kandimalla, E. R., Roskey, A., Zhao, Q., Chen, L., Chen, J. and Agrawal, S. (2000) Stereo-enriched phosphorothioate oligodeoxynucleotides: synthesis, biophysical and biological properties. Bioorg. Med. Chem., 8, 275-284.
    • (2000) Bioorg. Med. Chem. , vol.8 , pp. 275-284
    • Yu, D.1    Kandimalla, E.R.2    Roskey, A.3    Zhao, Q.4    Chen, L.5    Chen, J.6    Agrawal, S.7
  • 18
    • 81455144659 scopus 로고    scopus 로고
    • Stereocontrolled synthesis of oligonucleotide analogs containing chiral internucleotidic phosphorus atoms
    • Oka, N. and Wada, T. (2011) Stereocontrolled synthesis of oligonucleotide analogs containing chiral internucleotidic phosphorus atoms. Chem. Soc. Rev., 40, 5829-5843.
    • (2011) Chem. Soc. Rev. , vol.40 , pp. 5829-5843
    • Oka, N.1    Wada, T.2
  • 19
    • 0031299443 scopus 로고    scopus 로고
    • Phosphorothioate oligodeoxynucleotides: Large-scale synthesis and analysis, impurity characterization, and the effects of phosphorus stereochemistry
    • discussion 31-37
    • Fearon, K. L., Hirschbein, B. L., Chiu, C. Y., Quijano, M. R. and Zon, G. (1997) Phosphorothioate oligodeoxynucleotides: large-scale synthesis and analysis, impurity characterization, and the effects of phosphorus stereochemistry. Ciba Found. Symp., 209, 19-31, discussion 31-37.
    • (1997) Ciba Found. Symp. , vol.209 , pp. 19-31
    • Fearon, K.L.1    Hirschbein, B.L.2    Chiu, C.Y.3    Quijano, M.R.4    Zon, G.5
  • 21
    • 33750207033 scopus 로고    scopus 로고
    • Potent reduction of apolipoprotein B and LDL cholesterol by short-term administration of an antisense inhibitor of apolipoprotein B
    • Kastelein, J. J. P., Wedel, M. K., Baker, B. F., Su, J., Bradley, J. D., Yu, R. Z., Chuang, E., Graham, M. J. and Crooke, R. M. (2006) Potent reduction of apolipoprotein B and LDL cholesterol by short-term administration of an antisense inhibitor of apolipoprotein B. Circulation, 114, 1729-1735.
    • (2006) Circulation , vol.114 , pp. 1729-1735
    • Kastelein, J.J.P.1    Wedel, M.K.2    Baker, B.F.3    Su, J.4    Bradley, J.D.5    Yu, R.Z.6    Chuang, E.7    Graham, M.J.8    Crooke, R.M.9
  • 22
    • 84880668457 scopus 로고    scopus 로고
    • Clinical pharmacological properties of mipomersen (Kynamro), a second generation antisense inhibitor of apolipoprotein B
    • Crooke, S. T. and Geary, R. S. (2013) Clinical pharmacological properties of mipomersen (Kynamro), a second generation antisense inhibitor of apolipoprotein B. Br. J. Clin. Pharmacol., 76, 269-276.
    • (2013) Br. J. Clin. Pharmacol. , vol.76 , pp. 269-276
    • Crooke, S.T.1    Geary, R.S.2
  • 23
    • 78649877710 scopus 로고    scopus 로고
    • Short locked nucleic acid antisense oligonucleotides potently reduce apolipoprotein B mRNA and serum cholesterol in mice and non-human primates
    • Straarup, E. M., Fisker, N., Hedtjarn, M., Lindholm, M. W., Rosenbohm, C., Aarup, V., Hansen, H. F., Orum, H., Hansen, J. B. and Koch, T. (2010) Short locked nucleic acid antisense oligonucleotides potently reduce apolipoprotein B mRNA and serum cholesterol in mice and non-human primates. Nucleic Acids Res., 38, 7100-7111.
    • (2010) Nucleic Acids Res. , vol.38 , pp. 7100-7111
    • Straarup, E.M.1    Fisker, N.2    Hedtjarn, M.3    Lindholm, M.W.4    Rosenbohm, C.5    Aarup, V.6    Hansen, H.F.7    Orum, H.8    Hansen, J.B.9    Koch, T.10
  • 24
    • 59449093219 scopus 로고    scopus 로고
    • Short antisense oligonucleotides with novel 2'-4' conformationaly restricted nucleoside analogues show improved potency without increased toxicity in animals
    • Seth, P. P., Siwkowski, A., Allerson, C. R., Vasquez, G., Lee, S., Prakash, T. P., Wancewicz, E. V., Witchell, D. and Swayze, E. E. (2009) Short antisense oligonucleotides with novel 2'-4' conformationaly restricted nucleoside analogues show improved potency without increased toxicity in animals. J. Med. Chem., 52, 10-13.
    • (2009) J. Med. Chem. , vol.52 , pp. 10-13
    • Seth, P.P.1    Siwkowski, A.2    Allerson, C.R.3    Vasquez, G.4    Lee, S.5    Prakash, T.P.6    Wancewicz, E.V.7    Witchell, D.8    Swayze, E.E.9
  • 25
    • 80054756151 scopus 로고    scopus 로고
    • Synthesis, improved antisense activity and structural rationale for the divergent RNA affinities of 3'-fluoro hexitol nucleic acid (FHNA and Ara-FHNA) modified oligonucleotides
    • Egli, M., Pallan, P. S., Allerson, C. R., Prakash, T. P., Berdeja, A., Yu, J., Lee, S., Watt, A., Gaus, H., Bhat, B. et al. (2011) Synthesis, improved antisense activity and structural rationale for the divergent RNA affinities of 3'-fluoro hexitol nucleic acid (FHNA and Ara-FHNA) modified oligonucleotides. J. Am. Chem. Soc., 133, 16642-16649.
    • (2011) J. Am. Chem. Soc. , vol.133 , pp. 16642-16649
    • Egli, M.1    Pallan, P.S.2    Allerson, C.R.3    Prakash, T.P.4    Berdeja, A.5    Yu, J.6    Lee, S.7    Watt, A.8    Gaus, H.9    Bhat, B.10
  • 26
    • 21244451435 scopus 로고    scopus 로고
    • Crystal structures of RNase H bound to an RNA/DNA hybrid: Substrate specificity and metal-dependent catalysis
    • Nowotny, M., Gaidamakov, S. A., Crouch, R. J. and Yang, W. (2005) Crystal structures of RNase H bound to an RNA/DNA hybrid: substrate specificity and metal-dependent catalysis. Cell, 121, 1005-1016.
    • (2005) Cell , vol.121 , pp. 1005-1016
    • Nowotny, M.1    Gaidamakov, S.A.2    Crouch, R.J.3    Yang, W.4
  • 27
    • 41949083183 scopus 로고    scopus 로고
    • Specific recognition of RNA/DNA hybrid and enhancement of human RNase H1 activity by HBD
    • Nowotny, M., Cerritelli, S. M., Ghirlando, R., Gaidamakov, S. A., Crouch, R. J. and Yang, W. (2008) Specific recognition of RNA/DNA hybrid and enhancement of human RNase H1 activity by HBD. EMBO J., 27, 1172-1181.
    • (2008) EMBO J. , vol.27 , pp. 1172-1181
    • Nowotny, M.1    Cerritelli, S.M.2    Ghirlando, R.3    Gaidamakov, S.A.4    Crouch, R.J.5    Yang, W.6
  • 30
    • 56749161695 scopus 로고    scopus 로고
    • Solid-phase synthesis of stereoregular oligodeoxyribonucleoside phosphorothioates using bicyclic oxazaphospholidine derivatives as monomer units
    • Oka, N., Yamamoto, M., Sato, T. and Wada, T. (2008) Solid-phase synthesis of stereoregular oligodeoxyribonucleoside phosphorothioates using bicyclic oxazaphospholidine derivatives as monomer units. J. Am. Chem. Soc., 130, 16031-16037.
    • (2008) J. Am. Chem. Soc. , vol.130 , pp. 16031-16037
    • Oka, N.1    Yamamoto, M.2    Sato, T.3    Wada, T.4
  • 31
    • 0035427644 scopus 로고    scopus 로고
    • Hepatic distribution of a phosphorothioate oligodeoxynucleotide within rodents following intravenous administration
    • Graham, M. J., Crooke, S. T., Lemonidis, K. M., Gaus, H. J., Templin, M. V. and Crooke, R. M. (2001) Hepatic distribution of a phosphorothioate oligodeoxynucleotide within rodents following intravenous administration. Biochem. Pharmacol., 62, 297-306.
    • (2001) Biochem. Pharmacol. , vol.62 , pp. 297-306
    • Graham, M.J.1    Crooke, S.T.2    Lemonidis, K.M.3    Gaus, H.J.4    Templin, M.V.5    Crooke, R.M.6
  • 33
    • 0014645531 scopus 로고
    • High-yield preparation of isolated rat liver parenchymal cells: A biochemical and fine structural study
    • Berry, M. N. and Friend, D. S. (1969) High-yield preparation of isolated rat liver parenchymal cells: a biochemical and fine structural study. J. Cell Biol., 43, 506-520.
    • (1969) J. Cell Biol. , vol.43 , pp. 506-520
    • Berry, M.N.1    Friend, D.S.2
  • 34
    • 73349086270 scopus 로고    scopus 로고
    • Off-target and a portion of target-specific siRNA mediated mRNA degradation is Ago2 'Slicer' independent and can be mediated by Ago1
    • Vickers, T. A., Lima, W. F., Wu, H., Nichols, J. G., Linsley, P. S. and Crooke, S. T. (2009) Off-target and a portion of target-specific siRNA mediated mRNA degradation is Ago2 'Slicer' independent and can be mediated by Ago1. Nucleic Acids Res., 37, 6927-6941.
    • (2009) Nucleic Acids Res. , vol.37 , pp. 6927-6941
    • Vickers, T.A.1    Lima, W.F.2    Wu, H.3    Nichols, J.G.4    Linsley, P.S.5    Crooke, S.T.6
  • 38
    • 33646053453 scopus 로고    scopus 로고
    • Recent advances in the stereocontrolled synthesis of antisense phosphorothioates
    • Lu, Y. (2006) Recent advances in the stereocontrolled synthesis of antisense phosphorothioates. Mini-Rev. Med. Chem., 6, 319-330.
    • (2006) Mini-Rev. Med. Chem. , vol.6 , pp. 319-330
    • Lu, Y.1
  • 39
    • 0030046797 scopus 로고    scopus 로고
    • Identification of scavenger receptor SR-B1 as a high density lipoprotein receptor
    • Acton, S., Rigotti, A., Landschulz, K. T., Xu, S., Hobbs, H. H. and Krieger, M. (1996) Identification of scavenger receptor SR-B1 as a high density lipoprotein receptor. Science, 271, 518-520.
    • (1996) Science , vol.271 , pp. 518-520
    • Acton, S.1    Rigotti, A.2    Landschulz, K.T.3    Xu, S.4    Hobbs, H.H.5    Krieger, M.6
  • 40
    • 84864062473 scopus 로고    scopus 로고
    • TricycloDNA-modified oligo-2'-deoxyribonucleotides reduce scavenger receptor B1 mRNA in hepatic and extra-hepatic tissues - A comparative study of oligonucleotide length, design and chemistry
    • Murray, S., Ittig, D., Koller, E., Berdeja, A., Chappell, A., Prakash, T. P., Norrbom, M., Swayze, E. E., Leumann, C. J. and Seth, P. P. (2012) TricycloDNA-modified oligo-2'-deoxyribonucleotides reduce scavenger receptor B1 mRNA in hepatic and extra-hepatic tissues - a comparative study of oligonucleotide length, design and chemistry. Nucleic Acids Res., 40, 6135-6143.
    • (2012) Nucleic Acids Res. , vol.40 , pp. 6135-6143
    • Murray, S.1    Ittig, D.2    Koller, E.3    Berdeja, A.4    Chappell, A.5    Prakash, T.P.6    Norrbom, M.7    Swayze, E.E.8    Leumann, C.J.9    Seth, P.P.10
  • 42
    • 84899918530 scopus 로고    scopus 로고
    • Peripheral androgen receptor gene suppression rescues disease in mouse models of spinal and bulbar muscular atrophy
    • Lieberman, A. P., Yu, Z., Peralta, R., Murray, S., Low, A., Guo, S., Yu, X. X., Cortes, C. J., Bennett, C. F., Monia, B. P. et al. (2014) Peripheral androgen receptor gene suppression rescues disease in mouse models of spinal and bulbar muscular atrophy. Cell Rep., 7, 1-11.
    • (2014) Cell Rep. , vol.7 , pp. 1-11
    • Lieberman, A.P.1    Yu, Z.2    Peralta, R.3    Murray, S.4    Low, A.5    Guo, S.6    Yu, X.X.7    Cortes, C.J.8    Bennett, C.F.9    Monia, B.P.10
  • 43
    • 0033999899 scopus 로고    scopus 로고
    • Influence of diastereomeric ratios of deoxyribonucleoside phosphoramidites on the synthesis of phosphorothioate oligonucleotides
    • Cheruvallath, Z. S., Sasmor, H., Cole, D. L. and Ravikumar, V. T. (2000) Influence of diastereomeric ratios of deoxyribonucleoside phosphoramidites on the synthesis of phosphorothioate oligonucleotides. Nucleosides Nucleotides Nucleic Acids, 19, 533-543.
    • (2000) Nucleosides Nucleotides Nucleic Acids , vol.19 , pp. 533-543
    • Cheruvallath, Z.S.1    Sasmor, H.2    Cole, D.L.3    Ravikumar, V.T.4
  • 44
    • 62249220595 scopus 로고    scopus 로고
    • Screening the structural space of bicyclo-DNA: Synthesis and thermal melting properties of bc-DNA
    • Stauffiger, A. and Leumann, C. J. (2009) Screening the structural space of bicyclo-DNA: synthesis and thermal melting properties of bc-DNA. Eur. J. Org. Chem., 2009, 1153-1162.
    • (2009) Eur. J. Org. Chem. , vol.2009 , pp. 1153-1162
    • Stauffiger, A.1    Leumann, C.J.2
  • 45
    • 0347379925 scopus 로고    scopus 로고
    • Human RNase H1 uses one tryptophan and two lysines to position the enzyme at the 3'-DNA/5'-RNA terminus of the heteroduplex substrate
    • Lima, W. F., Wu, H., Nichols, J. G., Prakash, T. P., Ravikumar, V. and Crooke, S. T. (2003) Human RNase H1 uses one tryptophan and two lysines to position the enzyme at the 3'-DNA/5'-RNA terminus of the heteroduplex substrate. J. Biol. Chem., 278, 49860-49867.
    • (2003) J. Biol. Chem. , vol.278 , pp. 49860-49867
    • Lima, W.F.1    Wu, H.2    Nichols, J.G.3    Prakash, T.P.4    Ravikumar, V.5    Crooke, S.T.6
  • 46
    • 0000427396 scopus 로고
    • Synthesis of diribonucleoside phosphorothioates via stereospecific sulfuration of H-phosphonate diesters
    • Almer, H., Stawinski, J., Stroemberg, R. and Thelin, M. (1992) Synthesis of diribonucleoside phosphorothioates via stereospecific sulfuration of H-phosphonate diesters. J. Org. Chem., 57, 6163-6169.
    • (1992) J. Org. Chem. , vol.57 , pp. 6163-6169
    • Almer, H.1    Stawinski, J.2    Stroemberg, R.3    Thelin, M.4
  • 47
    • 0029817212 scopus 로고    scopus 로고
    • Oxathiaphospholane method of stereocontrolled synthesis of diribonucleoside 3', 5'-phosphorothioates
    • Sierzchala, A., Okruszek, A. and Stec, W. J. (1996) Oxathiaphospholane method of stereocontrolled synthesis of diribonucleoside 3', 5'-phosphorothioates. J. Org. Chem., 61, 6713-6716.
    • (1996) J. Org. Chem. , vol.61 , pp. 6713-6716
    • Sierzchala, A.1    Okruszek, A.2    Stec, W.J.3
  • 51
    • 0029609588 scopus 로고
    • Diastereomers of nucleoside 3'-O-(2-thio-1, 3, 2-oxathia (selena) phospholanes): Building blocks for stereocontrolled synthesis of oligo (nucleoside phosphorothioate) s
    • Stec, W. J., Grajkowski, A., Kobylanska, A., Karwowski, B., Koziolkiewicz, M., Misiura, K., Okruszek, A., Wilk, A., Guga, P. and Malgorzata, B. (1995) Diastereomers of nucleoside 3'-O-(2-thio-1, 3, 2-oxathia (selena) phospholanes): building blocks for stereocontrolled synthesis of oligo (nucleoside phosphorothioate) s. J. Am. Chem. Soc., 117, 12019-12029.
    • (1995) J. Am. Chem. Soc. , vol.117 , pp. 12019-12029
    • Stec, W.J.1    Grajkowski, A.2    Kobylanska, A.3    Karwowski, B.4    Koziolkiewicz, M.5    Misiura, K.6    Okruszek, A.7    Wilk, A.8    Guga, P.9    Malgorzata, B.10
  • 52
    • 14444274100 scopus 로고    scopus 로고
    • Porcine spleen deoxyribonuclease II. Covalent structure, cDNA sequence, molecular cloning, and gene expression
    • Wang, C. C., Lu, S. C., Chen, H. L. and Liao, T. H. (1998) Porcine spleen deoxyribonuclease II. Covalent structure, cDNA sequence, molecular cloning, and gene expression. J. Biol. Chem., 273, 17192-17198.
    • (1998) J. Biol. Chem. , vol.273 , pp. 17192-17198
    • Wang, C.C.1    Lu, S.C.2    Chen, H.L.3    Liao, T.H.4
  • 53
    • 0024202897 scopus 로고
    • Inhibition of deoxyribonucleases by phosphorothioate groups in oligodeoxyribonucleotides
    • Spitzer, S. and Eckstein, F. (1988) Inhibition of deoxyribonucleases by phosphorothioate groups in oligodeoxyribonucleotides. Nucleic Acids Res., 16, 11691-11704.
    • (1988) Nucleic Acids Res. , vol.16 , pp. 11691-11704
    • Spitzer, S.1    Eckstein, F.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.