메뉴 건너뛰기




Volumn 11, Issue 10, 1999, Pages 760-767

Gas chromatographic enantiomer separation of C-3 and C-4 synthons: Prediction of absolute configuration from elution order and enzymatic resolution

Author keywords

3 hydroxybutanoates; Absolute configuration; C 3 secondary alcohols; Chiral discrimination; Chiraldex G TA; CP Chirasil Dex CB; Cyclic 1,3 dithioacetals; Enantiomer separation; Lipase catalysis

Indexed keywords

ACETAL DERIVATIVE; BUTYRIC ACID;

EID: 0032714332     PISSN: 08990042     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1520-636X(1999)11:10<760::AID-CHIR4>3.0.CO;2-P     Document Type: Article
Times cited : (24)

References (42)
  • 1
    • 20644469267 scopus 로고
    • Quantitative analyses of biochemical kinetic resolutions of enantiomers
    • Chen C-S, Fujimoto Y, Girdaukas G, Sih CJ. Quantitative analyses of biochemical kinetic resolutions of enantiomers. J Am Chem Soc 1982; 104:7294-7299.
    • (1982) J Am Chem Soc , vol.104 , pp. 7294-7299
    • Chen, C.-S.1    Fujimoto, Y.2    Girdaukas, G.3    Sih, C.J.4
  • 2
    • 33845282987 scopus 로고
    • Quantitative analyses of biochemical kinetic resolution of enantiomers. 2. Enzyme-catalyzed esterifications in water-organic solvent biphasic systems
    • Chen C-S, Wu S, Girdaukas G, Sih CJ. Quantitative analyses of biochemical kinetic resolution of enantiomers. 2. Enzyme-catalyzed esterifications in water-organic solvent biphasic systems. J Am Chem Soc 1987;109:2812-2817.
    • (1987) J Am Chem Soc , vol.109 , pp. 2812-2817
    • Chen, C.-S.1    Wu, S.2    Girdaukas, G.3    Sih, C.J.4
  • 3
    • 0032102791 scopus 로고    scopus 로고
    • Resolution of derivatives of 1,2-propanediol with lipase b from Candida antarctica. Effect of substrate structure, medium, water activity and acyl donor on enantiomeric ratio
    • Anthonsen T, Hoff BH. Resolution of derivatives of 1,2-propanediol with lipase B from Candida antarctica. Effect of substrate structure, medium, water activity and acyl donor on enantiomeric ratio. Chem Phys Lipids 1998;93:199-207.
    • (1998) Chem Phys Lipids , vol.93 , pp. 199-207
    • Anthonsen, T.1    Hoff, B.H.2
  • 4
    • 0003572523 scopus 로고
    • Microbial resolution of 1-phenoxy-2-propanol by sterospecific decomposition and asymmetric hydrolysis of 1-phenoxy-2-propyl acetate
    • Yanase H, Arishima T, Kita K, Nagai J, Mizuno S, Takuma Y, Endo K, Kato N. Microbial resolution of 1-phenoxy-2-propanol by sterospecific decomposition and asymmetric hydrolysis of 1-phenoxy-2-propyl acetate. Biosci Biotech Biochem 1993;57:1334-1337.
    • (1993) Biosci Biotech Biochem , vol.57 , pp. 1334-1337
    • Yanase, H.1    Arishima, T.2    Kita, K.3    Nagai, J.4    Mizuno, S.5    Takuma, Y.6    Endo, K.7    Kato, N.8
  • 5
    • 0027241186 scopus 로고
    • Enzymatic resolution of butanoic esters of 1-phenylmethyl and 1-[2-phenylethyl]ethers of 3-chloro-1,2-propanediol
    • Partali V, Waagen V, Alvik T, Anthonsen T. Enzymatic resolution of butanoic esters of 1-phenylmethyl and 1-[2-phenylethyl]ethers of 3-chloro-1,2-propanediol. Tetrahedron Asymmetry 1993;4:961-968.
    • (1993) Tetrahedron Asymmetry , vol.4 , pp. 961-968
    • Partali, V.1    Waagen, V.2    Alvik, T.3    Anthonsen, T.4
  • 6
    • 0027491699 scopus 로고
    • Chromatographic resolution of chiral intermediates in β-adrenergic blocker synthesis on chiral stationary phases
    • Ader U, Muschalek V, Schneider M. Chromatographic resolution of chiral intermediates in β-adrenergic blocker synthesis on chiral stationary phases. Chirality 1993;7:554-559.
    • (1993) Chirality , vol.7 , pp. 554-559
    • Ader, U.1    Muschalek, V.2    Schneider, M.3
  • 7
    • 0028138933 scopus 로고
    • A practical asymmetric synthesis of a 1,7-enyne A-ring synthon en route toward the total synthesis of vitamin D3 analogs
    • Trost BM, Hanson PR. A practical asymmetric synthesis of a 1,7-enyne A-ring synthon en route toward the total synthesis of vitamin D3 analogs. Tetrahedron Lett 1994;35:8119-8122.
    • (1994) Tetrahedron Lett , vol.35 , pp. 8119-8122
    • Trost, B.M.1    Hanson, P.R.2
  • 8
    • 0000494506 scopus 로고
    • Chiral synthesis of a component of Amanita muscaria (-)-4-hydroxypyrrolidine-2-one, and assessment of its absolute configuration
    • Santaniello E, Casati R, Milani F. Chiral synthesis of a component of Amanita muscaria (-)-4-hydroxypyrrolidine-2-one, and assessment of its absolute configuration. J Chem Res (S) 1984:132-133.
    • (1984) J Chem Res (S) , pp. 132-133
    • Santaniello, E.1    Casati, R.2    Milani, F.3
  • 9
    • 0032485225 scopus 로고    scopus 로고
    • Efficient enantioselective synthesis of a β-hydroxyepoxide building block for the construction of macrocyclic natural products
    • Schiede U, Nazaré M, Waldmann H. Efficient enantioselective synthesis of a β-hydroxyepoxide building block for the construction of macrocyclic natural products. Tetrahedron Lett 1998;39:1143-1144.
    • (1998) Tetrahedron Lett , vol.39 , pp. 1143-1144
    • Schiede, U.1    Nazaré, M.2    Waldmann, H.3
  • 10
    • 0002174369 scopus 로고
    • A facile stereocontrolled entry to key intermediates for thienamycin synthesis from ethyl (S)-3-hydroxybutanoate
    • Chiba T, Nagatsuma M, Nakai T. A facile stereocontrolled entry to key intermediates for thienamycin synthesis from ethyl (S)-3-hydroxybutanoate. Chem Lett 1985:1343-1346.
    • (1985) Chem Lett , pp. 1343-1346
    • Chiba, T.1    Nagatsuma, M.2    Nakai, T.3
  • 11
    • 0031983501 scopus 로고    scopus 로고
    • Control of enantio-selectivity in Baker's yeast reduction of β-keto ester derivatives in the presence of a sulfur compound
    • Hayakawa R, Nozawa K, Shimizu M, Fujisawa T. Control of enantio-selectivity in Baker's yeast reduction of β-keto ester derivatives in the presence of a sulfur compound. Tetrahedron Lett 1998;39:667-70.
    • (1998) Tetrahedron Lett , vol.39 , pp. 667-670
    • Hayakawa, R.1    Nozawa, K.2    Shimizu, M.3    Fujisawa, T.4
  • 12
    • 4243570735 scopus 로고
    • Formation of the (R)- and (S)-enantiomers of ethyl 3-hydroxybutanoate and of 1-[1,3-dithiane-2-yl]-2-hydroxypropane by microbial reduction
    • Bernardi R, Cardillo R, Ghiringhelli D. Formation of the (R)- and (S)-enantiomers of ethyl 3-hydroxybutanoate and of 1-[1,3-dithiane-2-yl]-2-hydroxypropane by microbial reduction. J Chem Soc Chem Commun 1984:460-461.
    • (1984) J Chem Soc Chem Commun , pp. 460-461
    • Bernardi, R.1    Cardillo, R.2    Ghiringhelli, D.3
  • 13
    • 84985154137 scopus 로고
    • Production of (+)-(S)-ethyl 3-hydroxybutyrate and (-)-(R)-ethyl 3-hydroxybutyrate by microbial reduction of ethyl acetoacetate
    • Wipf B, Kupfer E, Bertazzi R, Leuenberger H. Production of (+)-(S)-ethyl 3-hydroxybutyrate and (-)-(R)-ethyl 3-hydroxybutyrate by microbial reduction of ethyl acetoacetate. Helv Chim Acta 1983;66:485-488.
    • (1983) Helv Chim Acta , vol.66 , pp. 485-488
    • Wipf, B.1    Kupfer, E.2    Bertazzi, R.3    Leuenberger, H.4
  • 14
    • 0343580463 scopus 로고    scopus 로고
    • The effect of absorbing resins on substrate concentration and enantiomer excess in yeast reductions
    • D'Arrigo P, Fantoni GP, Servi S, Strini A. The effect of absorbing resins on substrate concentration and enantiomer excess in yeast reductions. Tetrahedron Asymmetry 1997;8:2375-2379.
    • (1997) Tetrahedron Asymmetry , vol.8 , pp. 2375-2379
    • D'Arrigo, P.1    Fantoni, G.P.2    Servi, S.3    Strini, A.4
  • 15
    • 0030937174 scopus 로고    scopus 로고
    • The stereoselective preparation of β-hydroxy esters using yeast reduction in an organic solvent
    • Medson C, Smallridge A, Trewhella M. The stereoselective preparation of β-hydroxy esters using yeast reduction in an organic solvent. Tetrahedron Asymmetry 1997;8:1049-1054.
    • (1997) Tetrahedron Asymmetry , vol.8 , pp. 1049-1054
    • Medson, C.1    Smallridge, A.2    Trewhella, M.3
  • 16
    • 0001037379 scopus 로고
    • The use of organic solvent systems in yeast mediated reduction of ethyl acetoacetate
    • Jayasinghe L, Kodituwakku D, Smallridge A, Trewhella M. The use of organic solvent systems in yeast mediated reduction of ethyl acetoacetate. Bull Chem Soc Jpn 1994;67:2528-2531.
    • (1994) Bull Chem Soc Jpn , vol.67 , pp. 2528-2531
    • Jayasinghe, L.1    Kodituwakku, D.2    Smallridge, A.3    Trewhella, M.4
  • 17
    • 0000251294 scopus 로고
    • Biocatalytic, enantioselective preparation of (R)- and (S)-ethyl 4-chloro-3-hydroxybutanoate, a useful chiral synthon
    • Aragozzini F, Valenti M, Santaniello E, Ferraboschi P, Grisenti P. Biocatalytic, enantioselective preparation of (R)- and (S)-ethyl 4-chloro-3-hydroxybutanoate, a useful chiral synthon. Biocatalysis 1992;5:325-332.
    • (1992) Biocatalysis , vol.5 , pp. 325-332
    • Aragozzini, F.1    Valenti, M.2    Santaniello, E.3    Ferraboschi, P.4    Grisenti, P.5
  • 18
    • 0001346256 scopus 로고
    • On the steric course of Baker's yeast mediated reduction of alkyl 4-azido- and 4-bromo-oxobutyrate
    • Fuganti C, Grasselli P, Casati P, Carmeno M. On the steric course of Baker's yeast mediated reduction of alkyl 4-azido- and 4-bromo-oxobutyrate. Tetrahedron Lett 1985;26:101-104.
    • (1985) Tetrahedron Lett , vol.26 , pp. 101-104
    • Fuganti, C.1    Grasselli, P.2    Casati, P.3    Carmeno, M.4
  • 19
    • 0020699934 scopus 로고
    • A synthesis of (S,S)-(+)-grahamimycin A1
    • Ghiringhelli D. A synthesis of (S,S)-(+)-grahamimycin A1. Tetrahedron Lett 1983:24:287-290.
    • (1983) Tetrahedron Lett , vol.24 , pp. 287-290
    • Ghiringhelli, D.1
  • 20
    • 0024805452 scopus 로고
    • Synthesis of 1,5-bifunctionalized optically active 3-pentanol as a reversible chiral building block. Asymmetric reduction of 4-(1,3-dithiane-2-yl)-3-oxobutanoates with fermenting Baker's yeast
    • Chikashita H, Ohkawa K, Itho K. Synthesis of 1,5-bifunctionalized optically active 3-pentanol as a reversible chiral building block. Asymmetric reduction of 4-(1,3-dithiane-2-yl)-3-oxobutanoates with fermenting Baker's yeast. Bull Chem Soc Jpn 1989;62:3513-3517.
    • (1989) Bull Chem Soc Jpn , vol.62 , pp. 3513-3517
    • Chikashita, H.1    Ohkawa, K.2    Itho, K.3
  • 21
    • 45249125380 scopus 로고
    • Enzymatic preparation of optically active α- and β-hydroxyaldehydes
    • Blanchi D, Cesti P, Golini P. Enzymatic preparation of optically active α- and β-hydroxyaldehydes. Tetrahedron 1989;45:869-876.
    • (1989) Tetrahedron , vol.45 , pp. 869-876
    • Blanchi, D.1    Cesti, P.2    Golini, P.3
  • 22
    • 0001490117 scopus 로고
    • Separation of enantiomers on diluted permethylated β-cyclodextrin by high-resolution gas chromatography
    • Schurig V, Nowotny HP. Separation of enantiomers on diluted permethylated β-cyclodextrin by high-resolution gas chromatography. J Chromatogr 1988;441:155-163.
    • (1988) J Chromatogr , vol.441 , pp. 155-163
    • Schurig, V.1    Nowotny, H.P.2
  • 23
    • 84985200345 scopus 로고
    • Extending the scope of enantiomer separation on Chirasil-Dex by GLC: Comparison with permethylated β-Cyclodextrin dissolved in OV-1701
    • Schmalzing D, Jung M, Mayer S, Rickert J, Schurig V. Extending the scope of enantiomer separation on Chirasil-Dex by GLC: comparison with permethylated β-Cyclodextrin dissolved in OV-1701. J High Res Chromatogr 1992;15:723-729.
    • (1992) J High Res Chromatogr , vol.15 , pp. 723-729
    • Schmalzing, D.1    Jung, M.2    Mayer, S.3    Rickert, J.4    Schurig, V.5
  • 24
    • 0030923461 scopus 로고    scopus 로고
    • Lipase catalyzed resolution of α-hydroxymethyl sulfones. Determination of absolute configuration by semiempirical calculation of CD spectra and verification by X-ray structure analysis
    • Gais HJ, von der Weiden I, Fleischhauer J, Esser J, Raabe G. Lipase catalyzed resolution of α-hydroxymethyl sulfones. Determination of absolute configuration by semiempirical calculation of CD spectra and verification by X-ray structure analysis. Tetrahedron Asymmetry 1997; 8:3111-3123.
    • (1997) Tetrahedron Asymmetry , vol.8 , pp. 3111-3123
    • Gais, H.J.1    Von Der Weiden, I.2    Fleischhauer, J.3    Esser, J.4    Raabe, G.5
  • 25
    • 84988074627 scopus 로고
    • Separation of the enantiomers of stable atropisomeric polychlorinated biphenyls (PCBs) by multidimensional gas chromatography on Chirasil-Dex
    • Glausch A, Nicholson G, Fluck M, Schurig V. Separation of the enantiomers of stable atropisomeric polychlorinated biphenyls (PCBs) by multidimensional gas chromatography on Chirasil-Dex. J High Res Chromatogr 1994;17:347-349.
    • (1994) J High Res Chromatogr , vol.17 , pp. 347-349
    • Glausch, A.1    Nicholson, G.2    Fluck, M.3    Schurig, V.4
  • 26
    • 84988080219 scopus 로고
    • Extending the scope of enantiomer separation by capillary supercritical fluid chromatography on immobilized polysiloxane-anchored permethyl-β-cyclodextrin (Chirasil-Dex)
    • Jung M, Schurig V. Extending the scope of enantiomer separation by capillary supercritical fluid chromatography on immobilized polysiloxane-anchored permethyl-β-cyclodextrin (Chirasil-Dex). J High Res Chromatogr 1993;16:215-223.
    • (1993) J High Res Chromatogr , vol.16 , pp. 215-223
    • Jung, M.1    Schurig, V.2
  • 27
    • 84985209776 scopus 로고
    • Separation of enantiomers on immobilized polysiloxane-anchored permethyl-β-cyclodextrin (Chirasil-Dex) by supercritical fluid chromatography
    • Schurig V, Juvancz Z, Nicholson G, Schmalzing D. Separation of enantiomers on immobilized polysiloxane-anchored permethyl-β-cyclodextrin (Chirasil-Dex) by supercritical fluid chromatography. J High Res Chromatogr 1991;14:58-62.
    • (1991) J High Res Chromatogr , vol.14 , pp. 58-62
    • Schurig, V.1    Juvancz, Z.2    Nicholson, G.3    Schmalzing, D.4
  • 28
    • 0025351392 scopus 로고
    • 2,6-Di-O-pentyl-3-O-trifluoroacetyl cyclodextrin liquid stationary phases for capillary gas chromatographic separation of enantiomers
    • Li W-Y, Jin H, Armstrong D. 2,6-Di-O-pentyl-3-O-trifluoroacetyl cyclodextrin liquid stationary phases for capillary gas chromatographic separation of enantiomers. J Chromatogr 1990;509:303-324.
    • (1990) J Chromatogr , vol.509 , pp. 303-324
    • Li, W.-Y.1    Jin, H.2    Armstrong, D.3
  • 29
    • 0343435812 scopus 로고    scopus 로고
    • Whippany, NJ
    • Advanced separation technologies Inc. Chiraldex handbook, 5th ed. Whippany, NJ; 1996.
    • (1996) Chiraldex Handbook, 5th Ed.
  • 30
    • 84985232917 scopus 로고
    • Investigation into the GC separation of enantiomers on a trifluoroacetylated cyclodextrin. 1. Effect of analyte structure on stereoselectivity for alcohols
    • Smith I, Simpson C. Investigation into the GC separation of enantiomers on a trifluoroacetylated cyclodextrin. 1. Effect of analyte structure on stereoselectivity for alcohols. J High Res Chromatogr 1992;15:800-806.
    • (1992) J High Res Chromatogr , vol.15 , pp. 800-806
    • Smith, I.1    Simpson, C.2
  • 31
    • 0003177957 scopus 로고
    • Multiple enantioselective retention mechanisms on derivatized cyclodextrin gas chromatography on chiral stationary phases
    • Berthod A, Li W, Armstrong D. Multiple enantioselective retention mechanisms on derivatized cyclodextrin gas chromatography on chiral stationary phases. Anal Chem 1992;64:873-879.
    • (1992) Anal Chem , vol.64 , pp. 873-879
    • Berthod, A.1    Li, W.2    Armstrong, D.3
  • 32
    • 0030575815 scopus 로고    scopus 로고
    • Resolution of 1-phenoxy-, 1-phenyl-methoxy- and 1-(2-phenylethoxy)-2-propanol and their butanoates by hydrolysis with lipase B from Candida antarctica
    • Hoff BH, Waagen V, Anthonsen T. Resolution of 1-phenoxy-, 1-phenyl-methoxy- and 1-(2-phenylethoxy)-2-propanol and their butanoates by hydrolysis with lipase B from Candida antarctica. Tetrahedron Asymmetry 1996;7:3181-3186.
    • (1996) Tetrahedron Asymmetry , vol.7 , pp. 3181-3186
    • Hoff, B.H.1    Waagen, V.2    Anthonsen, T.3
  • 33
    • 0030575820 scopus 로고    scopus 로고
    • The enantiomer ratio strongly depends on the alkyl part of the acyl donor in transesterification with lipase B from Candida antarctica
    • Hoff BH, Anthonsen HW, Anthonsen T. The enantiomer ratio strongly depends on the alkyl part of the acyl donor in transesterification with lipase B from Candida antarctica. Tetrahedron Asymmetry 1996;7: 3187-3192.
    • (1996) Tetrahedron Asymmetry , vol.7 , pp. 3187-3192
    • Hoff, B.H.1    Anthonsen, H.W.2    Anthonsen, T.3
  • 34
    • 0344208365 scopus 로고    scopus 로고
    • Influence of substituents on enantiomeric ratio in transesterification of racemic C-3 synthons using lipase B from Candida antarctica
    • in press
    • Hoff BH, Ljones L, Rønstad A, Anthonsen T. Influence of substituents on enantiomeric ratio in transesterification of racemic C-3 synthons using lipase B from Candida antarctica. J Mol Catalysis B Enzymatic 1999;6 (in press).
    • (1999) J Mol Catalysis B Enzymatic , pp. 6
    • Hoff, B.H.1    Ljones, L.2    Rønstad, A.3    Anthonsen, T.4
  • 35
    • 84981422020 scopus 로고
    • Neue, süss schmeckende oxathiazinon-dioxide
    • Clauss K. Neue, süss schmeckende Oxathiazinon-dioxide. Liebigs Ann Chem 1980:494-502.
    • (1980) Liebigs Ann Chem , pp. 494-502
    • Clauss, K.1
  • 36
    • 0033538140 scopus 로고    scopus 로고
    • Lipase catalyzed resolution esters of 4-chloro-3-hydroxybutanoic acid. Effect of alkoxy group and solvent on enantiomeric ratio
    • Hoff BH, Anthonsen T. Lipase catalyzed resolution esters of 4-chloro-3-hydroxybutanoic acid. Effect of alkoxy group and solvent on enantiomeric ratio. Tetrahedron Asymmetry 1999;10:1401-1412.
    • (1999) Tetrahedron Asymmetry , vol.10 , pp. 1401-1412
    • Hoff, B.H.1    Anthonsen, T.2
  • 37
    • 0033125368 scopus 로고    scopus 로고
    • Synthesis of 1,3-dithianes and 1,3-dithiolanes. Baker's yeast reduction and lipase-catalyzed resolution for synthesis of enantiopure derivatives
    • Anthonsen T, Hoff BH, Hoffsløkken N, Skattebel L, Sundby E. Synthesis of 1,3-dithianes and 1,3-dithiolanes. Baker's yeast reduction and lipase-catalyzed resolution for synthesis of enantiopure derivatives, Acta Chem Scand 1999;53:360-365.
    • (1999) Acta Chem Scand , vol.53 , pp. 360-365
    • Anthonsen, T.1    Hoff, B.H.2    Hoffsløkken, N.3    Skattebel, L.4    Sundby, E.5
  • 38
    • 0032022820 scopus 로고    scopus 로고
    • Synthesis of amino acid functional siloxanes
    • Provatas A, Matisons JG. Synthesis of amino acid functional siloxanes. Polymer Preprints 1998;39:546-547.
    • (1998) Polymer Preprints , vol.39 , pp. 546-547
    • Provatas, A.1    Matisons, J.G.2
  • 39
    • 0030250088 scopus 로고    scopus 로고
    • Calculation of enantiomer ratio and equilibrium constants in biocatalytic ping-pong bi-bi resolutions
    • Anthonsen HW, Hoff BH, Anthonsen T. Calculation of enantiomer ratio and equilibrium constants in biocatalytic ping-pong bi-bi resolutions. Tetrahedron Asymmetry 1996;7:2633-2638.
    • (1996) Tetrahedron Asymmetry , vol.7 , pp. 2633-2638
    • Anthonsen, H.W.1    Hoff, B.H.2    Anthonsen, T.3
  • 40
    • 0029417196 scopus 로고
    • Crystallographic and molecular modeling studies of lipase B from Candida antarctica reveal a stereospecificity pocket for secondary alcohols
    • Uppenberg J, Øhrner N, Norin M, Hult K, Patkar S, Waagen V, Anthonsen T, Jones TA. Crystallographic and molecular modeling studies of lipase B from Candida antarctica reveal a stereospecificity pocket for secondary alcohols. Biochemistry 1995;34:16838-16851.
    • (1995) Biochemistry , vol.34 , pp. 16838-16851
    • Uppenberg, J.1    ØHrner, N.2    Norin, M.3    Hult, K.4    Patkar, S.5    Waagen, V.6    Anthonsen, T.7    Jones, T.A.8
  • 41
    • 0031887073 scopus 로고    scopus 로고
    • Molecular modeling of the entioselectivity in lipase-catalyzed transesterification reactions
    • Hæffner F, Norin T, Hult K. Molecular modeling of the entioselectivity in lipase-catalyzed transesterification reactions. Biophys J 1998;74: 1251-1262.
    • (1998) Biophys J , vol.74 , pp. 1251-1262
    • Hæffner, F.1    Norin, T.2    Hult, K.3
  • 42
    • 84985200124 scopus 로고
    • Enantiomer separation by eletrochromatography on capillaries coated with Chirasil-Dex
    • Mayer S, Schurig V. Enantiomer separation by eletrochromatography on capillaries coated with Chirasil-Dex. J High Res Chromatogr 1992; 15:129-131.
    • (1992) J High Res Chromatogr , vol.15 , pp. 129-131
    • Mayer, S.1    Schurig, V.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.