메뉴 건너뛰기




Volumn 44, Issue 12, 2005, Pages 4710-4719

Determining the origin of the stabilization of DNA by 5-aminopropynylation of pyrimidines

Author keywords

[No Author keywords available]

Indexed keywords

ELECTROSTATICS; FREE ENERGY; HYDRATION; IONIC STRENGTH; MELTING; NUCLEAR MAGNETIC RESONANCE; OXYGEN; PHOSPHATES; THERMODYNAMIC STABILITY;

EID: 15444368861     PISSN: 00062960     EISSN: None     Source Type: Journal    
DOI: 10.1021/bi047561d     Document Type: Article
Times cited : (13)

References (49)
  • 1
    • 0029121625 scopus 로고
    • Relative thermodynamic stability of DNA, RNA, and DNA-RNA hybrid duplexes - Relationship with base composition and structure
    • Lesnik, E. A., and Freier, S. M. (1995) Relative thermodynamic stability of DNA, RNA, and DNA-RNA hybrid duplexes - Relationship with base composition and structure, Biochemistry 34, 10807-10815.
    • (1995) Biochemistry , vol.34 , pp. 10807-10815
    • Lesnik, E.A.1    Freier, S.M.2
  • 3
    • 0035940485 scopus 로고    scopus 로고
    • C5-(1-Propynyl)-2′-deoxypyrimidines enhance mismatch penalties of DNA:RNA duplex formation
    • Barnes, T. W., and Turner, D. H. (2001) C5-(1-Propynyl)-2′- deoxypyrimidines enhance mismatch penalties of DNA:RNA duplex formation, Biochemistry 40, 12738-12745.
    • (2001) Biochemistry , vol.40 , pp. 12738-12745
    • Barnes, T.W.1    Turner, D.H.2
  • 4
    • 0034794425 scopus 로고    scopus 로고
    • Long-range cooperativity in molecular recognition of RNA by oligodeoxynucleotides, with multiple C5-1-propynyl pyrimidines
    • Barnes, T. W., and Turner, D. H. (2001) Long-range cooperativity in molecular recognition of RNA by oligodeoxynucleotides, with multiple C5-(1-propynyl pyrimidines, J. Am. Chem. Soc. 123, 4107-4118.
    • (2001) J. Am. Chem. Soc. , vol.123 , pp. 4107-4118
    • Barnes, T.W.1    Turner, D.H.2
  • 5
    • 0029943016 scopus 로고    scopus 로고
    • Potent and selective inhibition of gene expression by an antisense heptanucleotide
    • Wagner, R. W., Matteucci, M. D., Grant, D., Huang, T., and Froehler, B. C. (1996) Potent and selective inhibition of gene expression by an antisense heptanucleotide, Nat. Biotechnol. 14, 840-844.
    • (1996) Nat. Biotechnol. , vol.14 , pp. 840-844
    • Wagner, R.W.1    Matteucci, M.D.2    Grant, D.3    Huang, T.4    Froehler, B.C.5
  • 6
    • 0033560690 scopus 로고    scopus 로고
    • 5-(1-Propargylamino)-2′-deoxyuridine (U-P): A novel thymidine analogue for generating DNA triplexes with increased stability
    • Bijapur, J., Keppler, M. D., Bergqvist, S., Brown, T., and Fox, K. R. (1999) 5-(1-Propargylamino)-2′-deoxyuridine (U-P): a novel thymidine analogue for generating DNA triplexes with increased stability, Nucleic Acids Res. 27, 1802-1809.
    • (1999) Nucleic Acids Res. , vol.27 , pp. 1802-1809
    • Bijapur, J.1    Keppler, M.D.2    Bergqvist, S.3    Brown, T.4    Fox, K.R.5
  • 7
    • 0038043309 scopus 로고    scopus 로고
    • The solution structure of a DNA-RNA duplex containing 5-propynyl U and C; comparison with 5-Me modifications
    • Gyi, J. I., Gao, D., Conn, G. L., Trent, J. O., Brown, T., and Lane, A. N. (2003) The solution structure of a DNA-RNA duplex containing 5-propynyl U and C; comparison with 5-Me modifications, Nucleic Acids Res. 31, 2683-2693.
    • (2003) Nucleic Acids Res. , vol.31 , pp. 2683-2693
    • Gyi, J.I.1    Gao, D.2    Conn, G.L.3    Trent, J.O.4    Brown, T.5    Lane, A.N.6
  • 8
    • 0033550063 scopus 로고    scopus 로고
    • DNA triple helix formation at target sites containing several pyrimidine interruptions: Stabilization by protonated cytosine or 5-(1-propargylamino)
    • Gowers, D. M., Bijapur, J., Brown, T., and Fox, K. R. (1999) DNA triple helix formation at target sites containing several pyrimidine interruptions: stabilization by protonated cytosine or 5-(1-propargylamino), Biochemistry 38, 13747-13758.
    • (1999) Biochemistry , vol.38 , pp. 13747-13758
    • Gowers, D.M.1    Bijapur, J.2    Brown, T.3    Fox, K.R.4
  • 9
    • 0037039318 scopus 로고    scopus 로고
    • Chemical modification of the third strand: Differential effects on purine and pyrimidine triple helix formation
    • Mills, M., Arimondo, P. B., Lacroix, L., Garestier, T. S., Klump, H., and Mergny, J. L. (2002) Chemical modification of the third strand: Differential effects on purine and pyrimidine triple helix formation, Biochemistry 41, 357-366.
    • (2002) Biochemistry , vol.41 , pp. 357-366
    • Mills, M.1    Arimondo, P.B.2    Lacroix, L.3    Garestier, T.S.4    Klump, H.5    Mergny, J.L.6
  • 10
    • 0032574686 scopus 로고    scopus 로고
    • Solution structure of an intramolecular DNA triplex containing 5-(1-propynyl)-2′-deoxyuridine residues in the third strand
    • Phipps, A. K., Tarkoy, M., Schultze, P., and Feigon, J. (1998) Solution structure of an intramolecular DNA triplex containing 5-(1-propynyl)-2′- deoxyuridine residues in the third strand, Biochemistry 37, 5820-5830.
    • (1998) Biochemistry , vol.37 , pp. 5820-5830
    • Phipps, A.K.1    Tarkoy, M.2    Schultze, P.3    Feigon, J.4
  • 11
    • 0032971841 scopus 로고    scopus 로고
    • Triplex formation by oligonucleotides containing 5-(1-propynyl)-2 ′-deoxyuridine: Decreased magnesium dependence and improved intracellular gene targeting
    • Lacroix, L., Lacoste, J., Reddoch, J. F., Mergny, J. L., Levy, D. D., Seidman, M. M., Matteucci, M. D., and Glazer, P. M. (1999) Triplex formation by oligonucleotides containing 5-(1-propynyl)-2 ′-deoxyuridine: Decreased magnesium dependence and improved intracellular gene targeting, Biochemistry 38, 1893-1901.
    • (1999) Biochemistry , vol.38 , pp. 1893-1901
    • Lacroix, L.1    Lacoste, J.2    Reddoch, J.F.3    Mergny, J.L.4    Levy, D.D.5    Seidman, M.M.6    Matteucci, M.D.7    Glazer, P.M.8
  • 12
    • 0037062574 scopus 로고    scopus 로고
    • Stable DNA triple helix formation using oligonucleotides containing 2′-aminoethoxy,5-propargylamino-U
    • Sollogoub, M., Richard, A. J., Darby, R. A. J., Cuenoud, B., Brown, T., and Fox, K. R. (2002) Stable DNA triple helix formation using oligonucleotides containing 2′-aminoethoxy,5-propargylamino-U, Biochemistry 41, 7224-7231.
    • (2002) Biochemistry , vol.41 , pp. 7224-7231
    • Sollogoub, M.1    Richard, A.J.2    Darby, R.A.J.3    Cuenoud, B.4    Brown, T.5    Fox, K.R.6
  • 13
    • 0023794115 scopus 로고
    • Oligonucleotide labeling - A concise synthesis of a modified thymidine phosphoramidite
    • Cruickshank, K. A., and Stockwell, D. L. (1988) Oligonucleotide labeling - a concise synthesis of a modified thymidine phosphoramidite, Tetrahedron Lett. 29, 5221-5224.
    • (1988) Tetrahedron Lett. , vol.29 , pp. 5221-5224
    • Cruickshank, K.A.1    Stockwell, D.L.2
  • 14
    • 0032567180 scopus 로고    scopus 로고
    • Control over the localization of positive charge in DNA: The effect on duplex DNA and RNA stability
    • Heystek, L. E., Zhou, H. Q., Dande, P., and Gold, B. (1998) Control over the localization of positive charge in DNA: The effect on duplex DNA and RNA stability, J. Am. Chem. Soc. 120, 12165-12166.
    • (1998) J. Am. Chem. Soc. , vol.120 , pp. 12165-12166
    • Heystek, L.E.1    Zhou, H.Q.2    Dande, P.3    Gold, B.4
  • 16
    • 0032125593 scopus 로고    scopus 로고
    • A comparative study of the thermal-stability of oligodeoxyribonucleotides containing 5-substituted 2′ deoxyuridines
    • Ahmadian, M., Zhang, P. M., and Bergstrom, D. E. (1998) A comparative study of the thermal-stability of oligodeoxyribonucleotides containing 5-substituted 2′ deoxyuridines, Nucleic Acids Res. 26, 3127-3135.
    • (1998) Nucleic Acids Res. , vol.26 , pp. 3127-3135
    • Ahmadian, M.1    Zhang, P.M.2    Bergstrom, D.E.3
  • 17
    • 0033529318 scopus 로고    scopus 로고
    • A more unified picture for the thermodynamics of nucleic acid duplex melting: A characterisation by calorimetric and volumetric techniques
    • Chalikian, T. V., Völker, J., Plum, G. E., and Breslauer, K. J. (1999) A more unified picture for the thermodynamics of nucleic acid duplex melting: a characterisation by calorimetric and volumetric techniques, Proc. Natl. Acad. Sci. U.S.A. 96, 7853-7858.
    • (1999) Proc. Natl. Acad. Sci. U.S.A. , vol.96 , pp. 7853-7858
    • Chalikian, T.V.1    Völker, J.2    Plum, G.E.3    Breslauer, K.J.4
  • 18
    • 0033614819 scopus 로고    scopus 로고
    • Enthalpy and heat capacity changes for formation of an oligomeric DNA duplex: Interpretation of coupled processes of formation and association of single-stranded helices
    • Holbrook, J. A., Capp, M. W., Saecker, R. M., and Record, M. T. (1999) Enthalpy and heat capacity changes for formation of an oligomeric DNA duplex: interpretation of coupled processes of formation and association of single-stranded helices, Biochemistry 38, 8409-8422.
    • (1999) Biochemistry , vol.38 , pp. 8409-8422
    • Holbrook, J.A.1    Capp, M.W.2    Saecker, R.M.3    Record, M.T.4
  • 19
    • 0033544722 scopus 로고    scopus 로고
    • The energetics of HMG box interactions with DNA: Thermodynamic description of the target DNA duplexes
    • Jelesarov, I., Crane-Robinson, C., and Privalov, P. L. (1999) The energetics of HMG box interactions with DNA: thermodynamic description of the target DNA duplexes, J. Mol. Biol. 294, 981-995.
    • (1999) J. Mol. Biol. , vol.294 , pp. 981-995
    • Jelesarov, I.1    Crane-Robinson, C.2    Privalov, P.L.3
  • 20
    • 0034536719 scopus 로고    scopus 로고
    • Thermodynamics of nucleic acids and their interactions with ligands
    • Lane, A. N., and Jenkins, T. C. (2000) Thermodynamics of nucleic acids and their interactions with ligands, Q. Rev. Biophys. 33, 255-306.
    • (2000) Q. Rev. Biophys. , vol.33 , pp. 255-306
    • Lane, A.N.1    Jenkins, T.C.2
  • 21
    • 0032763957 scopus 로고    scopus 로고
    • Heat capacity effects on the melting of DNA. 1. General aspects
    • Rouzina, I., and Bloomfield, V. A. (1999) Heat capacity effects on the melting of DNA. 1. General aspects, Biophys. J. 77, 3242-3251.
    • (1999) Biophys. J. , vol.77 , pp. 3242-3251
    • Rouzina, I.1    Bloomfield, V.A.2
  • 22
    • 0032785904 scopus 로고    scopus 로고
    • Heat capacity effects on the melting of DNA. 2. Analysis of nearest-neighbor base-pair effects
    • Rouzina, I., and Bloomfield, V. A. (1999) Heat capacity effects on the melting of DNA. 2. Analysis of nearest-neighbor base-pair effects, Biophys. J. 77, 3252-3255.
    • (1999) Biophys. J. , vol.77 , pp. 3252-3255
    • Rouzina, I.1    Bloomfield, V.A.2
  • 23
    • 0029805937 scopus 로고    scopus 로고
    • Investigation of the structural basis for thermodynamic stabilities of tandem GU mismatches: Solution structure of (rGAGGUCUC)(2) by two-dimensional NMR and simulated annealing
    • McDowell, J. A., and Turner, D. H (1996) Investigation of the structural basis for thermodynamic stabilities of tandem GU mismatches: Solution structure of (rGAGGUCUC)(2) by two-dimensional NMR and simulated annealing, Biochemistry 35, 14077-14089.
    • (1996) Biochemistry , vol.35 , pp. 14077-14089
    • McDowell, J.A.1    Turner, D.H.2
  • 24
    • 0017820499 scopus 로고
    • Thermodynamic analysis of ion effects on binding and conformational equilibria of proteins and nucleic-acids - Roles of ion association or release, screening, and ion effects on water activity
    • Record, M. T., Anderson, C. F., and Lohman, T. M. (1978) Thermodynamic analysis of ion effects on binding and conformational equilibria of proteins and nucleic-acids - Roles of ion association or release, screening, and ion effects on water activity, Q. Rev. Biophys. 11, 103-178.
    • (1978) Q. Rev. Biophys. , vol.11 , pp. 103-178
    • Record, M.T.1    Anderson, C.F.2    Lohman, T.M.3
  • 25
    • 0025308916 scopus 로고
    • Ion distributions around DNA and other cylindrical polyions - Theoretical descriptions and physical implications
    • Anderson, C. F., and Record, M. T. (1990) ion distributions around DNA and other cylindrical polyions - Theoretical descriptions and physical implications, Annu. Rev. Biophys. Biophys. Chem. 19, 423-465.
    • (1990) Annu. Rev. Biophys. Biophys. Chem. , vol.19 , pp. 423-465
    • Anderson, C.F.1    Record, M.T.2
  • 27
    • 2642528650 scopus 로고    scopus 로고
    • Effect of the number of nucleic acid oligomer charges on the salt dependence of stability (ΔG°37) and melting temperature (Tm): NLPB analysis of experimental data
    • in press
    • Shkel, I. A., and Record, M. T., Jr. (2004) Effect of the number of nucleic acid oligomer charges on the salt dependence of stability (ΔG°37) and melting temperature (Tm): NLPB analysis of experimental data, Biochemistry (in press).
    • (2004) Biochemistry
    • Shkel, I.A.1    Record Jr., M.T.2
  • 28
    • 0033524401 scopus 로고    scopus 로고
    • Effects of hydration, ion release, and excluded volume on the melting of triplex and duplex DNA
    • Spink, C. H., and Chaires, J. B. (1999) Effects of hydration, ion release, and excluded volume on the melting of triplex and duplex DNA, Biochemistry 38, 496-508.
    • (1999) Biochemistry , vol.38 , pp. 496-508
    • Spink, C.H.1    Chaires, J.B.2
  • 32
    • 0029938421 scopus 로고    scopus 로고
    • Thermodynamics of base pairing
    • Turner, D. H. (1996) Thermodynamics of base pairing, Curr. Opin. Struct. Biol. 6, 299-304.
    • (1996) Curr. Opin. Struct. Biol. , vol.6 , pp. 299-304
    • Turner, D.H.1
  • 33
    • 0029968822 scopus 로고    scopus 로고
    • Improved nearest-neighbor parameters for predicting DNA duplex stability
    • SantaLucia, J., Jr., Allawi, H. T., and Seneviratne, P. A. (1996) Improved nearest-neighbor parameters for predicting DNA duplex stability, Biochemistry 35, 3555-3562.
    • (1996) Biochemistry , vol.35 , pp. 3555-3562
    • SantaLucia Jr., J.1    Allawi, H.T.2    Seneviratne, P.A.3
  • 34
    • 0017895903 scopus 로고
    • Molecular theory of polyelectrolyte solutions with applications to electrostatic properties of poly-nucleotides
    • Manning, G. S. (1978) Molecular theory of polyelectrolyte solutions with applications to electrostatic properties of poly-nucleotides, Q. Rev. Biophys. 11, 179-246.
    • (1978) Q. Rev. Biophys. , vol.11 , pp. 179-246
    • Manning, G.S.1
  • 35
    • 0032499635 scopus 로고    scopus 로고
    • The B-DNA dodecamer at high resolution reveals a spine of water on sodium
    • Shui, X. Q., McFail-Isom, L., Hu, G. G., and Williams, L. D. (1998) The B-DNA dodecamer at high resolution reveals a spine of water on sodium Biochemistry 37, 8341-8355.
    • (1998) Biochemistry , vol.37 , pp. 8341-8355
    • Shui, X.Q.1    McFail-Isom, L.2    Hu, G.G.3    Williams, L.D.4
  • 36
    • 2942699968 scopus 로고    scopus 로고
    • Hydration of ds-DNA and ss-DNA by neutron quasielastic scattering
    • Bastos, M., Castro, V., Mrevlishvili, G., and Teixeira, J. (2004) Hydration of ds-DNA and ss-DNA by neutron quasielastic scattering, Biophys. J. 86, 3822-3827.
    • (2004) Biophys. J. , vol.86 , pp. 3822-3827
    • Bastos, M.1    Castro, V.2    Mrevlishvili, G.3    Teixeira, J.4
  • 37
    • 0021105577 scopus 로고
    • Assignment of the non-exchangeable proton resonances of d(C-G-C-G-A-A-T-T-C-G-C-G) using two-dimensional nuclear magnetic-resonance methods
    • Hare, D. R., Wemmer, D. E., Chou, S. H., Drobny, G., and Reid, B. R. (1983) Assignment of the non-exchangeable proton resonances of d(C-G-C-G-A-A-T-T-C-G-C-G) using two-dimensional nuclear magnetic-resonance methods, J. Mol. Biol. 171, 319-336.
    • (1983) J. Mol. Biol. , vol.171 , pp. 319-336
    • Hare, D.R.1    Wemmer, D.E.2    Chou, S.H.3    Drobny, G.4    Reid, B.R.5
  • 38
    • 0025762608 scopus 로고
    • Conformation of the eco R1 dodecamer in solution and its interaction with the minor groove binding drug Berenil
    • Lane, A. N., Jenkins, T., Brown, T., and Neidle, S. (1991) Conformation of the eco R1 dodecamer in solution and its interaction with the minor groove binding drug Berenil, Biochemistry 30, 1372-1385.
    • (1991) Biochemistry , vol.30 , pp. 1372-1385
    • Lane, A.N.1    Jenkins, T.2    Brown, T.3    Neidle, S.4
  • 39
    • 0034608901 scopus 로고    scopus 로고
    • The NMR structure of a DNA dodecamer in an aqueous dilute liquid crystalline phase
    • Tjandra, N., Tate, S., Ono, A., Kainosho, M., and Bax, A. (2000) The NMR structure of a DNA dodecamer in an aqueous dilute liquid crystalline phase, J. Am. Chem. Soc. 122, 6190-6200.
    • (2000) J. Am. Chem. Soc. , vol.122 , pp. 6190-6200
    • Tjandra, N.1    Tate, S.2    Ono, A.3    Kainosho, M.4    Bax, A.5
  • 40
    • 0038725129 scopus 로고    scopus 로고
    • Overall structure and sugar dynamics of a DNA dodecamer from homo and heteronuclear dipolar couplings and P-31 chemical shift anisotropy
    • Wu, Z. G., Delaglio, F., Tjandra, N., Zhurkin, V. B., and Bax, A. (2003) Overall structure and sugar dynamics of a DNA dodecamer from homo and heteronuclear dipolar couplings and P-31 chemical shift anisotropy, J. Biomol. 26, 297-315.
    • (2003) J. Biomol. , vol.26 , pp. 297-315
    • Wu, Z.G.1    Delaglio, F.2    Tjandra, N.3    Zhurkin, V.B.4    Bax, A.5
  • 41
    • 0026726087 scopus 로고
    • Furanose sugar conformations in DNA from NMR coupling-constants
    • Van Wijk, J., Huckriede, B. D., Ippel, J. H., and Altona, C. (1992) Furanose sugar conformations in DNA from NMR coupling-constants, Methods Enzymol. 211, 286-306.
    • (1992) Methods Enzymol. , vol.211 , pp. 286-306
    • Van Wijk, J.1    Huckriede, B.D.2    Ippel, J.H.3    Altona, C.4
  • 42
    • 0026758712 scopus 로고
    • Solution structure of a DNA octamer containing the Pribnow box via restrained molecular-dynamics simulation with distance and torsion angle constraints derived from 2-dimensional nuclear-magnetic-resonance spectral fitting
    • Schmitz, U., Sethson, I., Egan, W. M., and James, T. L. (1992) Solution structure of a DNA octamer containing the Pribnow box via restrained molecular-dynamics simulation with distance and torsion angle constraints derived from 2-dimensional nuclear-magnetic-resonance spectral fitting, J. Mol. Biol. 227, 510-531.
    • (1992) J. Mol. Biol. , vol.227 , pp. 510-531
    • Schmitz, U.1    Sethson, I.2    Egan, W.M.3    James, T.L.4
  • 44
    • 0028296359 scopus 로고
    • Thermodynamic stability and solution conformation of tandem G.A mismatches in RNA and RNA-DNA hybrid duplexes
    • Ebel, S., Brown, T., and Lane, A. N. (1994) Thermodynamic stability and solution conformation of tandem G.A mismatches in RNA and RNA-DNA hybrid duplexes, Eur. J. Biochem. 220, 703-715.
    • (1994) Eur. J. Biochem. , vol.220 , pp. 703-715
    • Ebel, S.1    Brown, T.2    Lane, A.N.3
  • 45
    • 0028310908 scopus 로고
    • P-31 chemical-shift as a probe of structural motifs in RNA
    • Legault, P., and Pardi, A. (1994) P-31 chemical-shift as a probe of structural motifs in RNA, J. Magn. Reson. B 103, 82-86.
    • (1994) J. Magn. Reson. B , vol.103 , pp. 82-86
    • Legault, P.1    Pardi, A.2
  • 46
    • 0034741617 scopus 로고    scopus 로고
    • 31P chemical shift anisotropy as an aid in determining nucleic acid structure in liquid crystals
    • 31P chemical shift anisotropy as an aid in determining nucleic acid structure in liquid crystals, J. Am. Chem. Soc. 123, 3617-3618.
    • (2001) J. Am. Chem. Soc. , vol.123 , pp. 3617-3618
    • Wu, Z.1    Tjandra, N.2    Bax, A.3
  • 47
    • 0001200839 scopus 로고
    • P-31 NMR spectral-analysis of the dodecamer d(CGCGAATTCGCG)
    • Ott, J., and Eckstein, F. (1985) P-31 NMR spectral-analysis of the dodecamer d(CGCGAATTCGCG), Biochemistry 24, 2530-2535.
    • (1985) Biochemistry , vol.24 , pp. 2530-2535
    • Ott, J.1    Eckstein, F.2
  • 48
    • 0027058824 scopus 로고
    • NMR observation of individual molecules of hydration water bound to dna duplexes - Direct evidence for a spine of hydration water present in aqueous-solution
    • Liepinsh, E., Otting, G., and Wuthrich, K. (1992) NMR observation of individual molecules of hydration water bound to dna duplexes - Direct evidence for a spine of hydration water present in aqueous-solution, Nucleic Acids Res. 20, 6549-6553.
    • (1992) Nucleic Acids Res. , vol.20 , pp. 6549-6553
    • Liepinsh, E.1    Otting, G.2    Wuthrich, K.3
  • 49
    • 0028363804 scopus 로고
    • Hydration of DNA in aqueous-solution - NMR evidence for a kinetic destabilization of the minor-groove hydration of d-(TTAA)(2) versus D-(AATT)-(2) segments
    • Liepinsh, E., Leupin, W., and Otting, G. (1994) Hydration of DNA in aqueous-solution - NMR evidence for a kinetic destabilization of the minor-groove hydration of d-(TTAA)(2) versus D-(AATT)-(2) segments, Nucleic Acids Res. 22, 2249-2254.
    • (1994) Nucleic Acids Res. , vol.22 , pp. 2249-2254
    • Liepinsh, E.1    Leupin, W.2    Otting, G.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.