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Volumn 54, Issue 14, 2011, Pages 4964-4976

Design, synthesis, and X-ray crystallographic studies of α-aryl substituted fosmidomycin analogues as inhibitors of mycobacterium tuberculosis 1-deoxy-d-xylulose 5-phosphate reductoisomerase

Author keywords

[No Author keywords available]

Indexed keywords

1 DEOXY D XYLULOSE 5 PHOSPHATE REDUCTOISOMERASE; 3 (N HYDROXYACETAMIDO) 1 (3,4 DICHLOROPHENYL)PROPYLPHOSPHONIC ACID; 3 (N HYDROXYFORMAMIDO) 1 (3,4 DICHLOROPHENYL)PROPYLPHOSPHONIC ACID; [3 (N HYDROXYACETAMIDO) 1 PHENYL]PROPYLPHOSPHONIC ACID; DIETHYL [1 (3,4 DICHLOROPHENYL) 3 (N HYDROXYACETAMIDO)PROPYL]PHOSPHONATE; DIETHYL [1 (3,4 DICHLOROPHENYL) 3 (N HYDROXYFORMAMIDO)PROPYL]PHOSPHONATE; FOSMIDOMYCIN; OXIDOREDUCTASE; UNCLASSIFIED DRUG;

EID: 79960652249     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm2000085     Document Type: Article
Times cited : (62)

References (55)
  • 1
    • 0030846307 scopus 로고    scopus 로고
    • Creating isoprenoid diversity
    • DOI 10.1126/science.277.5333.1788
    • Sacchettini, J. C.; Poulter, C. D. Creating isoprenoid diversity Science 1997, 277, 1788-1789 (Pubitemid 27449183)
    • (1997) Science , vol.277 , Issue.5333 , pp. 1788-1789
    • Sacchettini, J.C.1    Poulter, C.D.2
  • 2
    • 0033513375 scopus 로고    scopus 로고
    • The 1-deoxy-D-xylulose-5-phosphate pathway of isoprenoid biosynthesis in plants
    • Lichtenthaler, H. K. The 1-deoxy- d -xylulose-5-phosphate pathway of isoprenoid biosynthesis in plants Annu. Rev. Plant Physiol. Plant Mol. Biol. 1999, 50, 47-65 (Pubitemid 129493120)
    • (1999) Annual Review of Plant Biology , vol.50 , pp. 47-65
    • Lichtenthaler, H.K.1
  • 3
    • 0033213706 scopus 로고    scopus 로고
    • The discovery of a mevalonate-independent pathway for isoprenoid biosynthesis in bacteria, algae and higher plants
    • DOI 10.1039/a709175c
    • Rohmer, M. The discovery of a mevalonate-independent pathway for isoprenoid biosynthesis in bacteria, algae and higher plants Nat. Prod. Rep. 1999, 16, 565-574 (Pubitemid 29501611)
    • (1999) Natural Product Reports , vol.16 , Issue.5 , pp. 565-574
    • Rohmer, M.1
  • 4
    • 0027368126 scopus 로고
    • Isoprenoid biosynthesis in bacteria: A novel pathway for the early steps leading to isopentenyl diphosphate
    • Rohmer, M.; Knani, M.; Simonin, P.; Sutter, B.; Sahm, H. Isoprenoid biosynthesis in bacteria: a novel pathway for the early steps leading to isopentenyl diphosphate Biochem. J. 1993, 295, 517-524 (Pubitemid 23315192)
    • (1993) Biochemical Journal , vol.295 , Issue.2 , pp. 517-524
    • Rohmer, M.1    Knani, M.2    Simonin, P.3    Sutter, B.4    Sahm, H.5
  • 5
    • 0033859551 scopus 로고    scopus 로고
    • The role of lateral gene transfer in the evolution of isoprenoid biosynthesis pathways
    • DOI 10.1046/j.1365-2958.2000.02004.x
    • Boucher, Y.; Doolittle, W. F. The role of lateral gene transfer in the evolution of isoprenoid biosynthesis pathways Mol. Microbiol. 2000, 37, 703-716 (Pubitemid 30618134)
    • (2000) Molecular Microbiology , vol.37 , Issue.4 , pp. 703-716
    • Boucher, Y.1    Ford Doolittle, W.2
  • 8
    • 0032544054 scopus 로고    scopus 로고
    • A 1-deoxy-D-xylulose 5-phosphate reductoisomerase catalyzing the formation of 2-C-methyl-D-erythritol 4-phosphate in an alternative nonmevalonate pathway for terpenoid biosynthesis
    • DOI 10.1073/pnas.95.17.9879
    • Takahashi, S.; Kuzuyama, T.; Watanabe, H.; Seto, H. A 1-deoxy- d -xylulose 5-phosphate reductoisomerase catalyzing the formation of 2- C -methyl- d -erythritol 4-phosphate in an alternative nonmevalonate pathway for terpenoid biosynthesis Proc. Natl. Acad. Sci. U.S.A. 1998, 95, 9879-9884 (Pubitemid 28415263)
    • (1998) Proceedings of the National Academy of Sciences of the United States of America , vol.95 , Issue.17 , pp. 9879-9884
    • Takahashi, S.1    Kuzuyama, T.2    Watanabe, H.3    Seto, H.4
  • 9
    • 0034685844 scopus 로고    scopus 로고
    • Genetic evidence of branching in the isoprenoid pathway for the production of isopentenyl diphosphate and dimethylallyl diphosphate in Escherichia coli
    • DOI 10.1016/S0014-5793(00)01552-0, PII S0014579300015520
    • Rodriguez-Concepcion, M.; Campos, N.; Lois, L. M.; Maldonado, C.; Hoeffler, J. F.; Grosdemange-Billiard, C.; Rohmer, M.; Boronat, A. Genetic evidence of branching in the isoprenoid pathway for the production of isopentenyl diphosphate and dimethylallyl diphosphate in Escherichia coli FEBS Lett. 2000, 473, 328-332 (Pubitemid 30249148)
    • (2000) FEBS Letters , vol.473 , Issue.3 , pp. 328-332
    • Rodriguez-Concepcion, M.1    Campos, N.2    Maria Lois, L.3    Maldonado, C.4    Hoeffler, J.-F.5    Grosdemange-Billiard, C.6    Rohmer, M.7    Boronat, A.8
  • 10
    • 44849135047 scopus 로고    scopus 로고
    • Dxr is essential in Mycobacterium tuberculosis and fosmidomycin resistance is due to a lack of uptake
    • Brown, A. C.; Parish, T. Dxr is essential in Mycobacterium tuberculosis and fosmidomycin resistance is due to a lack of uptake BMC Microbiol. 2008, 8, 78
    • (2008) BMC Microbiol. , vol.8 , pp. 78
    • Brown, A.C.1    Parish, T.2
  • 12
    • 0024421915 scopus 로고
    • Inhibition of bacterial isoprenoid synthesis by fosmidomycin, a phosphonic acid-containing antibiotic
    • Shigi, Y. Inhibition of bacterial isoprenoid synthesis by fosmidomycin, a phosphonic acid-containing antibiotic J. Antimicrob. Chemother. 1989, 24, 131-145 (Pubitemid 19220017)
    • (1989) Journal of Antimicrobial Chemotherapy , vol.24 , Issue.2 , pp. 131-145
    • Shigi, Y.1
  • 14
    • 0032558613 scopus 로고    scopus 로고
    • Fosmidomycin, a specific inhibitor of 1-deoxy-D-xylulose 5-phosphate reductoisomerase in the nonmevalonate pathway for terpenoid biosynthesis
    • DOI 10.1016/S0040-4039(98)01755-9, PII S0040403998017559
    • Kuzuyama, T.; Shimizu, T.; Takahashi, S.; Seto, H. Fosmidomycin, a specific inhibitor of 1-deoxy- d -xylulose 5-phosphate reductoisomerase in the nonmevalonate pathway for terpenoid biosynthesis Tetrahedron Lett. 1998, 39, 7913-7916 (Pubitemid 28475040)
    • (1998) Tetrahedron Letters , vol.39 , Issue.43 , pp. 7913-7916
    • Kuzuyama, T.1    Shimizu, T.2    Takahashi, S.3    Seto, H.4
  • 15
    • 45549085673 scopus 로고    scopus 로고
    • Towards new antimalarial drugs: Synthesis of non-hydrolyzable phosphate mimics as feed for a predictive QSAR study on 1-deoxy- d -xylulose-5-phosphate reductoisomerase inhibitors
    • Giessmann, D.; Heidler, P.; Haemers, T.; Van Calenbergh, S.; Reichenberg, A.; Jomaa, H.; Weidemeyer, C.; Sanderbrand, S.; Wiesner, J.; Link, A. Towards new antimalarial drugs: synthesis of non-hydrolyzable phosphate mimics as feed for a predictive QSAR study on 1-deoxy- d -xylulose-5-phosphate reductoisomerase inhibitors Chem. Biodiversity 2008, 5, 643-656
    • (2008) Chem. Biodiversity , vol.5 , pp. 643-656
    • Giessmann, D.1    Heidler, P.2    Haemers, T.3    Van Calenbergh, S.4    Reichenberg, A.5    Jomaa, H.6    Weidemeyer, C.7    Sanderbrand, S.8    Wiesner, J.9    Link, A.10
  • 16
  • 20
    • 28844484972 scopus 로고    scopus 로고
    • 1-Deoxy-D-xylulose 5-phosphate reductoisomerase (IspC) from Mycobacterium tuberculosis: Towards understanding mycobacterial resistance to fosmidomycin
    • DOI 10.1128/JB.187.24.8395-8402.2005
    • Dhiman, R. K.; Schaeffer, M. L.; Bailey, A. M.; Testa, C. A.; Scherman, H.; Crick, D. C. 1-Deoxy- d -xylulose 5-phosphate reductoisomerase (IspC) from Mycobacterium tuberculosis: towards understanding mycobacterial resistance to fosmidomycin J. Bacteriol. 2005, 187, 8395-8402 (Pubitemid 41780504)
    • (2005) Journal of Bacteriology , vol.187 , Issue.24 , pp. 8395-8402
    • Dhiman, R.K.1    Schaeffer, M.L.2    Bailey, A.M.3    Testa, C.A.4    Scherman, H.5    Crick, D.C.6
  • 21
    • 2842613801 scopus 로고    scopus 로고
    • Fosmidomycin resistance in adenylate cyclase deficient (cya) mutants of Escherichia coli
    • DOI 10.1271/bbb.67.2030
    • Sakamoto, Y.; Furukawa, S.; Ogihara, H.; Yamasaki, M. Fosmidomycin resistance in adenylate cyclase deficient (cya) mutants of Escherichia coli Biosci., Biotechnol., Biochem. 2003, 67, 2030-2033 (Pubitemid 39251734)
    • (2003) Bioscience, Biotechnology and Biochemistry , vol.67 , Issue.9 , pp. 2030-2033
    • Sakamoto, Y.1    Furukawa, S.2    Ogihara, H.3    Yamasaki, M.4
  • 24
    • 18744377281 scopus 로고    scopus 로고
    • AFMoC enhances predictivity of 3D QSAR: A case study with DOXP-reductoisomerase
    • DOI 10.1021/jm0491501
    • Silber, K.; Heidler, P.; Kurz, T.; Klebe, G. AFMoC enhances predictivity of 3D QSAR: a case study with DOXP-reductoisomerase J. Med. Chem. 2005, 48, 3547-3563 (Pubitemid 40667523)
    • (2005) Journal of Medicinal Chemistry , vol.48 , Issue.10 , pp. 3547-3563
    • Silber, K.1    Heidler, P.2    Kurz, T.3    Klebe, G.4
  • 25
    • 77954734834 scopus 로고    scopus 로고
    • Synthesis and evaluation of α-halogenated analogues of 3-(acetylhydroxyamino)propylphosphonic acid (FR900098) as antimalarials
    • Verbrugghen, T.; Cos, P.; Maes, L.; Van Calenbergh, S. Synthesis and evaluation of α-halogenated analogues of 3-(acetylhydroxyamino) propylphosphonic acid (FR900098) as antimalarials J. Med. Chem. 2010, 53, 5342-5346
    • (2010) J. Med. Chem. , vol.53 , pp. 5342-5346
    • Verbrugghen, T.1    Cos, P.2    Maes, L.3    Van Calenbergh, S.4
  • 26
    • 77952475238 scopus 로고    scopus 로고
    • Isoprenoid biosynthesis via the methylerythritol phosphate pathway: Structural variations around phosphonate anchor and spacer of fosmidomycin, a potent inhibitor of deoxyxylulose phosphate reductoisomerase
    • Zinglé, C.; Kuntz, L.; Tritsch, D.; Grosdemange-Billiard, C.; Rohmer, M. Isoprenoid biosynthesis via the methylerythritol phosphate pathway: structural variations around phosphonate anchor and spacer of fosmidomycin, a potent inhibitor of deoxyxylulose phosphate reductoisomerase J. Org. Chem. 2010, 75, 3203-3207
    • (2010) J. Org. Chem. , vol.75 , pp. 3203-3207
    • Zinglé, C.1    Kuntz, L.2    Tritsch, D.3    Grosdemange-Billiard, C.4    Rohmer, M.5
  • 28
    • 32844461335 scopus 로고    scopus 로고
    • Evaluation of fosmidomycin analogs as inhibitors of the Synechocystis sp. PCC6803 1-deoxy-D-xylulose 5-phosphate reductoisomerase
    • DOI 10.1016/j.bmc.2005.11.012, PII S096808960501076X
    • Woo, Y. H.; Fernandes, R. P. M.; Proteau, P. J. Evaluation of fosmidomycin analogs as inhibitors of the Synechocystis sp. PCC6803 1-deoxy- d -xylulose 5-phosphate reductoisomerase Bioorg. Med. Chem. 2006, 14, 2375-2385 (Pubitemid 43254746)
    • (2006) Bioorganic and Medicinal Chemistry , vol.14 , Issue.7 , pp. 2375-2385
    • Woo, Y.-H.1    Fernandes, R.P.M.2    Proteau, P.J.3
  • 29
    • 54449085013 scopus 로고    scopus 로고
    • Studies addressing the importance of charge in the binding of fosmidomycin-like molecules to deoxyxylulosephosphate reductoisomerase
    • Perruchon, J.; Ortmann, R.; Altenkamper, M.; Silber, K.; Wiesner, J.; Jomaa, H.; Klebe, G.; Schlitzer, M. Studies addressing the importance of charge in the binding of fosmidomycin-like molecules to deoxyxylulosephosphate reductoisomerase ChemMedChem 2008, 3, 1232-1241
    • (2008) ChemMedChem , vol.3 , pp. 1232-1241
    • Perruchon, J.1    Ortmann, R.2    Altenkamper, M.3    Silber, K.4    Wiesner, J.5    Jomaa, H.6    Klebe, G.7    Schlitzer, M.8
  • 30
    • 33748525177 scopus 로고    scopus 로고
    • Synthesis of α-aryl-substituted and conformationally restricted fosmidomycin analogues as promising antimalarials
    • Haemers, T.; Wiesner, J.; Busson, R.; Jomaa, H.; Van Calenbergh, S. Synthesis of α-aryl-substituted and conformationally restricted fosmidomycin analogues as promising antimalarials Eur. J. Org. Chem. 2006, 3856-3863
    • (2006) Eur. J. Org. Chem. , pp. 3856-3863
    • Haemers, T.1    Wiesner, J.2    Busson, R.3    Jomaa, H.4    Van Calenbergh, S.5
  • 31
    • 34447623874 scopus 로고    scopus 로고
    • Structures of Mycobacterium tuberculosis 1-deoxy-D-xylulose-5-phosphate reductoisomerase provide new insights into catalysis
    • DOI 10.1074/jbc.M701935200
    • Henriksson, L. M.; Unge, T.; Carlsson, J.; Åqvist, J.; Mowbray, S. L.; Jones, T. A. Structures of Mycobacterium tuberculosis 1-deoxy- d -xylulose-5-phosphate reductoisomerase provide new insights into catalysis J. Biol. Chem. 2007, 282, 19905-19916 (Pubitemid 47100071)
    • (2007) Journal of Biological Chemistry , vol.282 , Issue.27 , pp. 19905-19916
    • Henriksson, L.M.1    Unge, T.2    Carlsson, J.3    Aqvist, J.4    Mowbray, S.L.5    Jones, T.A.6
  • 32
    • 33745659845 scopus 로고    scopus 로고
    • The 1.9 Å resolution structure of Mycobacterium tuberculosis 1-deoxy-D-xylulose 5-phosphate reductoisomerase, a potential drug target
    • DOI 10.1107/S0907444906019196
    • Henriksson, L. M.; Björkelid, C.; Mowbray, S. L.; Unge, T. The 1.9 Å resolution structure of Mycobacterium tuberculosis 1-deoxy- d -xylulose 5-phosphate reductoisomerase, a potential drug target Acta Crystallogr., Sect. D: Biol. Crystallogr. 2006, 62, 807-813 (Pubitemid 43965907)
    • (2006) Acta Crystallographica Section D: Biological Crystallography , vol.62 , Issue.7 , pp. 807-813
    • Henriksson, L.M.1    Bjorkelid, C.2    Mowbray, S.L.3    Unge, T.4
  • 33
    • 0037085356 scopus 로고    scopus 로고
    • Crystal structure of 1-deoxy-D-xylulose-5-phosphate reductoisomerase, a crucial enzyme in the non-mevalonate pathway of isoprenoid biosynthesis
    • DOI 10.1074/jbc.M109500200
    • Reuter, K.; Sanderbrand, S.; Jomaa, H.; Wiesner, J.; Steinbrecher, I.; Beck, E.; Hintz, M.; Klebe, G.; Stubbs, M. T. Crystal structure of 1-deoxy- d -xylulose-5-phosphate reductoisomerase, a crucial enzyme in the non-mevalonate pathway of isoprenoid biosynthesis J. Biol. Chem. 2002, 277, 5378-5384 (Pubitemid 34968584)
    • (2002) Journal of Biological Chemistry , vol.277 , Issue.7 , pp. 5378-5384
    • Reuter, K.1    Sanderbrand, S.2    Jomaa, H.3    Wiesner, J.4    Steinbrecher, I.5    Beck, E.6    Hintz, M.7    Klebe, G.8    Stubbs, M.T.9
  • 34
    • 84889120137 scopus 로고
    • Improved methods for building protein models in electron density maps and the location of errors in these models
    • Jones, T. A.; Zou, J. Y.; Cowan, S. W.; Kjeldgaard, M. Improved methods for building protein models in electron density maps and the location of errors in these models Acta Crystallogr., Sect. A 1991, 47, 110-119
    • (1991) Acta Crystallogr., Sect. A , vol.47 , pp. 110-119
    • Jones, T.A.1    Zou, J.Y.2    Cowan, S.W.3    Kjeldgaard, M.4
  • 36
    • 84944812409 scopus 로고
    • Improved fourier coefficients for maps using phases from partial structures with errors
    • Read, R. J. Improved fourier coefficients for maps using phases from partial structures with errors Acta Crystallogr., Sect. A 1986, 42, 140-149
    • (1986) Acta Crystallogr., Sect. A , vol.42 , pp. 140-149
    • Read, R.J.1
  • 38
    • 35348851364 scopus 로고    scopus 로고
    • Efficient palladium(II) catalysis under air. Base-free oxidative heck reactions at room temperature or with microwave heating
    • DOI 10.1021/jo701434s
    • Lindh, J.; Enquist, P. A.; Pilotti, Å.; Nilsson, P.; Larhed, M. Efficient palladium(II) catalysis under air. Base-free oxidative Heck reactions at room temperature or with microwave heating J. Org. Chem. 2007, 72, 7957-7962 (Pubitemid 47582581)
    • (2007) Journal of Organic Chemistry , vol.72 , Issue.21 , pp. 7957-7962
    • Lindh, J.1    Enquist, P.-A.2    Pilotti, A.3    Nilsson, P.4    Larhed, M.5
  • 39
    • 0038824420 scopus 로고    scopus 로고
    • An efficient palladium-catalyzed synthesis of cinnamaldehydes from acrolein diethyl acetal and aryl iodides and bromides
    • DOI 10.1021/ol034071p
    • Battistuzzi, G.; Cacchi, S.; Fabrizi, G. An efficient palladium-catalyzed synthesis of cinnamaldehydes from acrolein diethyl acetal and aryl iodides and bromides Org. Lett. 2003, 5, 777-780 (Pubitemid 37141101)
    • (2003) Organic Letters , vol.5 , Issue.5 , pp. 777-780
    • Battistuzzi, G.1    Cacchi, S.2    Fabrizi, G.3
  • 40
    • 0000153468 scopus 로고    scopus 로고
    • Microwave-promoted palladium-catalyzed coupling reactions
    • Larhed, M.; Hallberg, A. Microwave-promoted palladium-catalyzed coupling reactions J. Org. Chem. 1996, 61, 9582-9584 (Pubitemid 127562828)
    • (1996) Journal of Organic Chemistry , vol.61 , Issue.26 , pp. 9582-9584
    • Larhed, M.1    Hallberg, A.2
  • 42
    • 0034680614 scopus 로고    scopus 로고
    • Fast microwave-assisted preparation of aryl and vinyl nitriles and the corresponding tetrazoles from organo-halides
    • Alterman, M.; Hallberg, A. Fast microwave-assisted preparation of aryl and vinyl nitriles and the corresponding tetrazoles from organo-halides J. Org. Chem. 2000, 65, 7984-7989
    • (2000) J. Org. Chem. , vol.65 , pp. 7984-7989
    • Alterman, M.1    Hallberg, A.2
  • 46
    • 20444381685 scopus 로고    scopus 로고
    • Including tightly-bound water molecules in de novo drug design. exemplification through the in silico generation of poly(ADP-ribose)polymerase ligands
    • DOI 10.1021/ci049694b
    • Garcia-Sosa, A. T.; Firth-Clark, S.; Mancera, R. L. Including tightly-bound water molecules in de novo drug design. Exemplification through the in silico generation of poly (ADP-ribose)polymerase ligands J. Chem. Inf. Model. 2005, 45, 624-633 (Pubitemid 40795166)
    • (2005) Journal of Chemical Information and Modeling , vol.45 , Issue.3 , pp. 624-633
    • Garcia-Sosa, A.T.1    Firth-Clark, S.2    Mancera, R.L.3
  • 50
    • 0032543467 scopus 로고    scopus 로고
    • Direct formation of 2-C-methyl-D-erythritol 4-phosphate from 1-deoxy-D- xylulose 5-phosphate by 1-deoxy-D-xylulose 5-phosphate reductoisomerase, a new enzyme in the non-mevalonate pathway to isopentenyl diphosphate
    • DOI 10.1016/S0040-4039(98)00802-8, PII S0040403998008028
    • Kuzuyama, T.; Takahashi, S.; Watanabe, H.; Seto, H. Direct formation of 2- C -methyl- d -erythritol 4-phosphate from 1-deoxy- d -xylulose 5-phosphate by 1-deoxy- d -xylulose 5-phosphate reductoisomerase, a new enzyme in the non-mevalonate pathway to isopentenyl diphosphate Tetrahedron Lett. 1998, 39, 4509-4512 (Pubitemid 28255269)
    • (1998) Tetrahedron Letters , vol.39 , Issue.25 , pp. 4509-4512
    • Kuzuyama, T.1    Takahashi, S.2    Watanabe, H.3    Seto, H.4
  • 51
    • 50849088964 scopus 로고    scopus 로고
    • Evaluation of killing kinetics of anti-tuberculosis drugs on Mycobacterium tuberculosis using a bacteriophage-based assay
    • Marcel, N.; Nahta, A.; Balganesh, M. Evaluation of killing kinetics of anti-tuberculosis drugs on Mycobacterium tuberculosis using a bacteriophage-based assay Chemotherapy 2008, 54, 404-411
    • (2008) Chemotherapy , vol.54 , pp. 404-411
    • Marcel, N.1    Nahta, A.2    Balganesh, M.3
  • 52
    • 84856071275 scopus 로고    scopus 로고
    • version 55211; Schrödinger, LLC: New York, NY
    • Glide, version 55211; Schrödinger, LLC: New York, NY, 2009.
    • (2009) Glide
  • 53
    • 84856072055 scopus 로고    scopus 로고
    • version 9.0; Schrödinger, LLC: New York, NY
    • Maestro, version 9.0; Schrödinger, LLC: New York, NY, 2009.
    • (2009) Maestro
  • 54
    • 79960646455 scopus 로고    scopus 로고
    • Tripos: St. Louis, MO
    • Legion; Tripos: St. Louis, MO, 1998.
    • (1998) Legion
  • 55
    • 84856070368 scopus 로고    scopus 로고
    • version 2.3; Schrödinger, LLC: New York, NY
    • LigPrep, version 2.3; Schrödinger, LLC: New York, NY, 2009.
    • (2009) LigPrep


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