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Volumn 14, Issue 10, 2010, Pages 1022-1036

Stereochemical assingment of β-lactam antibiotics and their analogues by electronic circular dichroism spectroscopy

Author keywords

[No Author keywords available]

Indexed keywords

ANTIBIOTICS; CIRCULAR DICHROISM SPECTROSCOPY; DENSITY FUNCTIONAL THEORY; DICHROISM;

EID: 77954923311     PISSN: 13852728     EISSN: None     Source Type: Journal    
DOI: 10.2174/138527210791130497     Document Type: Article
Times cited : (21)

References (61)
  • 2
    • 0014938290 scopus 로고
    • Molecular architecture of the cephalosporins. Insights into biological activity based on structural investigations
    • Sweet, R.M.; Dahl, L.I. Molecular architecture of the cephalosporins. Insights into biological activity based on structural investigations. J. Am. Chem. Soc., 1970, 92, 5489-5507.
    • (1970) J. Am. Chem. Soc , vol.92 , pp. 5489-5507
    • Sweet, R.M.1    Dahl, L.I.2
  • 3
    • 0015835194 scopus 로고
    • Electronic structures of cephalosporins and penicillins. 2. Disulfide and beta-lactam chromophores. Structure-activity relations
    • Boyd, D.B. Electronic structures of cephalosporins and penicillins. 2. Disulfide and beta-lactam chromophores. Structure-activity relations. J. Med. Chem., 1973, 16, 1195-1199.
    • (1973) J. Med. Chem , vol.16 , pp. 1195-1199
    • Boyd, D.B.1
  • 6
    • 85196228289 scopus 로고
    • Recent Advances in the Chemistry and Biology of β-Lactams and β-Lactams Antibiotics
    • Georg, G.I., Ed
    • Georg, G.I., Ed. Recent Advances in the Chemistry and Biology of β-Lactams and β-Lactams Antibiotics. Bioorg. Med. Chem. Lett., 1993, 3, 2159-2164.
    • (1993) Bioorg. Med. Chem. Lett , vol.3 , pp. 2159-2164
  • 8
    • 37049101498 scopus 로고
    • Clavulanic acid and its derivatives. Structure elucidation of clavulanic acid and the preparation of dihydroclavulanic acid, isoclavulanic acid, esters and related oxidation products
    • Brown, A.G.; Corbett, D. F.; Goodacre, J.; Harbridge, J. B.; Howarth, T. T.; Ponsford, R.J.; Stirling, I.; King, T.J. Clavulanic acid and its derivatives. Structure elucidation of clavulanic acid and the preparation of dihydroclavulanic acid, isoclavulanic acid, esters and related oxidation products. J. Chem. Soc., Perkin Trans. 1, 1984, 635-650.
    • (1984) J. Chem. Soc., Perkin Trans , vol.1 , pp. 635-650
    • Brown, A.G.1    Corbett, D.F.2    Goodacre, J.3    Harbridge, J.B.4    Howarth, T.T.5    Ponsford, R.J.6    Stirling, I.7    King, T.J.8
  • 9
    • 0017819169 scopus 로고
    • Synthesis of Oxapenam Derivatives
    • Oida, S.; Yoshida, A.; Ohki, E. Synthesis of Oxapenam Derivatives. Chem. Pharm. Bull., 1978, 26, 448-455.
    • (1978) Chem. Pharm. Bull , vol.26 , pp. 448-455
    • Oida, S.1    Yoshida, A.2    Ohki, E.3
  • 12
    • 0041460302 scopus 로고
    • Structures of three novel β-lactams isolated from Streptomyces clavuligerus
    • Brown, D.; Evans, J.R.; Fletton, R.A. Structures of three novel β-lactams isolated from Streptomyces clavuligerus. J. Chem. Soc., Chem. Commun., 1979, 282-283.
    • (1979) J. Chem. Soc., Chem. Commun , pp. 282-283
    • Brown, D.1    Evans, J.R.2    Fletton, R.A.3
  • 13
    • 0019417121 scopus 로고
    • Ein neues antifungisches β-lactam-antibioticum der clavam-reihe
    • Wanning, M.; Zähner, H.; Krone, B.; Zeeck, A. Ein neues antifungisches β-lactam-antibioticum der clavam-reihe. Tetrahedron Lett., 1981, 22, 2539-2540.
    • (1981) Tetrahedron Lett , vol.22 , pp. 2539-2540
    • Wanning, M.1    Zähner, H.2    Krone, B.3    Zeeck, A.4
  • 14
    • 0022649396 scopus 로고
    • Clavamycins, new clavam antibiotics from two variants of streptomyces hygroscopicus. I. Taxonomy of the producing organisms fermentation, and biological activities
    • King, H.D.; Langhaerig, J.; Sanglier, J.J. Clavamycins, new clavam antibiotics from two variants of streptomyces hygroscopicus. I. Taxonomy of the producing organisms fermentation, and biological activities. J. Antibiot., 1986, 39, 510-515.
    • (1986) J. Antibiot , vol.39 , pp. 510-515
    • King, H.D.1    Langhaerig, J.2    Sanglier, J.J.3
  • 15
    • 0022632338 scopus 로고
    • Clavamycins, new clavam antibiotics from two variants of streptomyces hygroscopicus. II. Isolation and structures of clavamycins A, B and C clavamycins D, E and F form Streptomyces Hygroscopicus
    • Naegeli, H.V.; Loosli, H.-R.; Nussbaumer, A. Clavamycins, new clavam antibiotics from two variants of streptomyces hygroscopicus. II. Isolation and structures of clavamycins A, B and C clavamycins D, E and F form Streptomyces Hygroscopicus. J. Antibiot., 1986, 39, 516-524.
    • (1986) J. Antibiot , vol.39 , pp. 516-524
    • Naegeli, H.V.1    Loosli, H.-R.2    Nussbaumer, A.3
  • 16
    • 0025110369 scopus 로고
    • Synthesis and biological properties of 1-oxapenems
    • Murakami, M.; Aoki, T.; Matsuura, M.; Nagata, W. Synthesis and biological properties of 1-oxapenems. J. Antibiot., 1990, 43, 1441-1449.
    • (1990) J. Antibiot , vol.43 , pp. 1441-1449
    • Murakami, M.1    Aoki, T.2    Matsuura, M.3    Nagata, W.4
  • 17
    • 84913158033 scopus 로고
    • Stable oxapenem-3-carboxylic acids - a new class of β-lactam antibiotics. Influence of 2- and 6-alkyl substituents
    • Pfaendler, H.R.; Hendel, W. Stable oxapenem-3-carboxylic acids - a new class of β-lactam antibiotics. Influence of 2- and 6-alkyl substituents. Z. Naturforschung, B., 1992, 47, 1037-1049.
    • (1992) Z. Naturforschung, B , vol.47 , pp. 1037-1049
    • Pfaendler, H.R.1    Hendel, W.2
  • 18
    • 0026441137 scopus 로고
    • First synthetic access to 6-(methylene) oxapenems: A new class of beta-lactamase inhibitors
    • Wild, H.; Hartwig, W. First synthetic access to 6-(methylene) oxapenems: A new class of beta-lactamase inhibitors. Synthesis, 1992, 1099-1103.
    • (1992) Synthesis , pp. 1099-1103
    • Wild, H.1    Hartwig, W.2
  • 19
    • 0027723197 scopus 로고
    • Substituted 6-alkyloxapenems: Potent β-lactamase inhibitors: Synthesis and biological characterization
    • Wild, H.; Metzger, K.-G. Substituted 6-alkyloxapenems: potent β-lactamase inhibitors: synthesis and biological characterization. Bioorg. Med. Chem. Lett., 1993, 3, 2205-2210.
    • (1993) Bioorg. Med. Chem. Lett , vol.3 , pp. 2205-2210
    • Wild, H.1    Metzger, K.-G.2
  • 20
    • 0032030156 scopus 로고    scopus 로고
    • A benzo-fused oxapenem from a β-lactam-4-ylidene
    • Couture, P.; Warkentin, J. A benzo-fused oxapenem from a β-lactam-4-ylidene. Can. J. Chem., 1998, 76, 241-244.
    • (1998) Can. J. Chem , vol.76 , pp. 241-244
    • Couture, P.1    Warkentin, J.2
  • 21
    • 0016341606 scopus 로고
    • Total synthesis of beta-lactam antibiotics. VII. Total synthesis of (+/)-1-oxacephalothin
    • Cama, L.D.; Christensen, B.G. Total synthesis of beta-lactam antibiotics. VII. Total synthesis of (+/)-1-oxacephalothin. J. Am. Chem. Soc., 1974, 96, 7582-7584.
    • (1974) J. Am. Chem. Soc , vol.96 , pp. 7582-7584
    • Cama, L.D.1    Christensen, B.G.2
  • 24
    • 0000648394 scopus 로고
    • Contribution to the chemistry of β-lactam antibiotics: 1-oxa nuclear analogs of naturally occurring β-lactam antibiotics
    • Nagata, W. Contribution to the chemistry of β-lactam antibiotics: 1-oxa nuclear analogs of naturally occurring β-lactam antibiotics. Pure Appl. Chem., 1989, 61, 325-336.
    • (1989) Pure Appl. Chem , vol.61 , pp. 325-336
    • Nagata, W.1
  • 25
  • 26
    • 0038503309 scopus 로고
    • Novel 2-Methyl-1-oxacephalosporins 1. Synthesis of 2-methyl-3-nor-1-oxacephem nucleus
    • Okonogi, T.; Shibahara, S.; Murai, Y.; Inouye, S.; Kondo, S. Novel 2-Methyl-1-oxacephalosporins 1. Synthesis of 2-methyl-3-nor-1-oxacephem nucleus. Heterocycles, 1990, 31, 791-795.
    • (1990) Heterocycles , vol.31 , pp. 791-795
    • Okonogi, T.1    Shibahara, S.2    Murai, Y.3    Inouye, S.4    Kondo, S.5
  • 28
    • 0023099966 scopus 로고
    • Imipenem - Cilastatin: A reivew of its anti-bacterial activity, pharmacokinetic properties and therapeutic efficacy
    • Clissold, S.P.; Todd, P.A.; Campoli Richards, D.M. Imipenem - Cilastatin: A reivew of its anti-bacterial activity, pharmacokinetic properties and therapeutic efficacy. Drugs, 1987, 33, 183-241.
    • (1987) Drugs , vol.33 , pp. 183-241
    • Clissold, S.P.1    Todd, P.A.2    Campoli Richards, D.M.3
  • 30
    • 15844377845 scopus 로고    scopus 로고
    • Selectivity of ertapenem for Pseudomonas aeruginosa mutants cross-resistant to other carbapenems
    • Livermore, D.M.; Mushtaq, S.; Warner, M. Selectivity of ertapenem for Pseudomonas aeruginosa mutants cross-resistant to other carbapenems. J. Antimicrob. Chemother., 2005, 55, 306-311.
    • (2005) J. Antimicrob. Chemother , vol.55 , pp. 306-311
    • Livermore, D.M.1    Mushtaq, S.2    Warner, M.3
  • 32
    • 0033792721 scopus 로고    scopus 로고
    • Clavulanic acid, a β-lactamase inhibitor: Biosynthsis and molecular genetics
    • Liras, P.; Rodriguez-Garcia, A. Clavulanic acid, a β-lactamase inhibitor: biosynthsis and molecular genetics. Appl. Microbiol. Biotechnol., 2000, 54, 467-475.
    • (2000) Appl. Microbiol. Biotechnol , vol.54 , pp. 467-475
    • Liras, P.1    Rodriguez-Garcia, A.2
  • 33
    • 33646386406 scopus 로고    scopus 로고
    • Gene clusters for β-lactam antibiotics and control of their expression: Why have clusters evolved, and from where did they originate
    • Liras, P.; Martin, J. F. Gene clusters for β-lactam antibiotics and control of their expression: Why have clusters evolved, and from where did they originate? Int. Microbiol., 2006, 9, 9-19.
    • (2006) Int. Microbiol , vol.9 , pp. 9-19
    • Liras, P.1    Martin, J.F.2
  • 34
    • 0031214349 scopus 로고    scopus 로고
    • Chemistry and biosynthesis of clavulanic acid and other clavams
    • Baggaley, K.H.; Brown, A.G.; Schofield, C.J. Chemistry and biosynthesis of clavulanic acid and other clavams. Nat. Prod. Rep., 1997, 309-333.
    • (1997) Nat. Prod. Rep , pp. 309-333
    • Baggaley, K.H.1    Brown, A.G.2    Schofield, C.J.3
  • 35
    • 0000727123 scopus 로고    scopus 로고
    • Asymmetric synthesis of building-blocks for peptides and peptidomimetics by means of the β-lactam synthon method
    • Ojima, I.; Delaloge, F. Asymmetric synthesis of building-blocks for peptides and peptidomimetics by means of the β-lactam synthon method. Chem. Soc. Rev., 1997, 26, 377-386.
    • (1997) Chem. Soc. Rev , vol.26 , pp. 377-386
    • Ojima, I.1    Delaloge, F.2
  • 36
    • 0002925635 scopus 로고
    • δ-Lactone Cotton-effekt und Konformation des δ-Lactonringes
    • Wolf, H. δ-Lactone Cotton-effekt und Konformation des δ-Lactonringes. Tetrahedron Lett., 1966, 7, 5151-5156.
    • (1966) Tetrahedron Lett , vol.7 , pp. 5151-5156
    • Wolf, H.1
  • 37
    • 33947321475 scopus 로고
    • Symmetry rules for optical rotation
    • Schellman, J. Symmetry rules for optical rotation. Accts. Chem. Res., 1968, 1, 144-151.
    • (1968) Accts. Chem. Res , vol.1 , pp. 144-151
    • Schellman, J.1
  • 38
    • 0001487064 scopus 로고
    • Circulardichroismus und absolute Konfiguration von β-Lactamen
    • Rehling, H.; Jensen, H. Circulardichroismus und absolute Konfiguration von β-Lactamen Tetrahedron Lett., 1972, 27, 2793-2796.
    • (1972) Tetrahedron Lett , vol.27 , pp. 2793-2796
    • Rehling, H.1    Jensen, H.2
  • 39
    • 0000313591 scopus 로고
    • Conformation of (-)-menthone lactam and N-methylmenthone lactam
    • Ogura, H.; Takayanagi, H.; Kubo, K.; Furuhata, K. Lactam. III. Conformation of (-)-menthone lactam and N-methylmenthone lactam. J. Am. Chem. Soc., 1973, 95, 8056-8059.
    • (1973) J. Am. Chem. Soc , vol.95 , pp. 8056-8059
    • Ogura, H.1    Takayanagi, H.2    Kubo, K.3    Furuhata III, K.L.4
  • 40
    • 36749120296 scopus 로고
    • Sector rules for rotatory strength of low symmetry chromophores: Lactones, lactams, and peptides
    • Ong, E.; Cusachs, L.; Weigang, O. Sector rules for rotatory strength of low symmetry chromophores: Lactones, lactams, and peptides. J. Chem. Phys., 1977, 67, 3289-3297.
    • (1977) J. Chem. Phys , vol.67 , pp. 3289-3297
    • Ong, E.1    Cusachs, L.2    Weigang, O.3
  • 41
    • 0000303328 scopus 로고
    • Chiroptical properties of 4-azatricyclo[4.4.0.0]Decan-5-one - a lactam with a non-planar cis-amide group
    • Fric, I.; Malon, P.; Tichy, M.; Blaha, K. Chiroptical properties of 4-azatricyclo[4.4.0.0]Decan-5-one - a lactam with a non-planar cis-amide group. Coll. Czech. Chem. Commun., 1976, 42, 678-686.
    • (1976) Coll. Czech. Chem. Commun , vol.42 , pp. 678-686
    • Fric, I.1    Malon, P.2    Tichy, M.3    Blaha, K.4
  • 42
    • 0008639783 scopus 로고
    • 1. Long-wavelength circular dichroism of β-thiolactams (2-azetiodimethiones)
    • 1. Long-wavelength circular dichroism of β-thiolactams (2-azetiodimethiones). Croat. Chem. Acta, 1989, 62, 129-134.
    • (1989) Croat. Chem. Acta , vol.62 , pp. 129-134
    • Polonski, T.1    Milewska, M.J.2
  • 44
    • 0032476151 scopus 로고    scopus 로고
    • Assessment of the absolute configuration of a series of (3R)-3-hydroxy-3-alkyl-β-lactams
    • Barbaro, G.; Battaglia, A.; Guerrini, A.; Bertucci, C.; Geremia, S. Assessment of the absolute configuration of a series of (3R)-3-hydroxy-3-alkyl-β-lactams. Tetrahedron Asymmetry, 1998, 9, 3401-3409.
    • (1998) Tetrahedron Asymmetry , vol.9 , pp. 3401-3409
    • Barbaro, G.1    Battaglia, A.2    Guerrini, A.3    Bertucci, C.4    Geremia, S.5
  • 45
    • 0028293782 scopus 로고
    • Stereochemistry and chiroptical properties of 1,3-dialkylaziridinones (α-lactams). Chiral rules for the nonplanar amide chromophore
    • Shustov, G.; Kachanov, A.; Chervin, I.; Kostyanovsky, R.; Rauk, A. Stereochemistry and chiroptical properties of 1,3-dialkylaziridinones (α-lactams). Chiral rules for the nonplanar amide chromophore. Can. J. Chem., 1994, 72, 279-286.
    • (1994) Can. J. Chem , vol.72 , pp. 279-286
    • Shustov, G.1    Kachanov, A.2    Chervin, I.3    Kostyanovsky, R.4    Rauk, A.5
  • 46
    • 38449101399 scopus 로고    scopus 로고
    • Spectroscopic properties of the nonplanar amide group: A computational study
    • Bednarova, L.; Malon, P.; Bour, P. Spectroscopic properties of the nonplanar amide group: A computational study. Chirality, 2007, 19, 775-786.
    • (2007) Chirality , vol.19 , pp. 775-786
    • Bednarova, L.1    Malon, P.2    Bour, P.3
  • 47
    • 0017086011 scopus 로고
    • Electronic structures of cephalosporins and penicillins. 5. Optical activity of the penicillin nucleus chromophores
    • Boyd, D. B.; Yeh, C.; Richardson, F. S. Electronic structures of cephalosporins and penicillins. 5. Optical activity of the penicillin nucleus chromophores. J. Am. Chem. Soc., 1976, 98, 6100-6106.
    • (1976) J. Am. Chem. Soc , vol.98 , pp. 6100-6106
    • Boyd, D.B.1    Yeh, C.2    Richardson, F.S.3
  • 48
    • 0000195955 scopus 로고
    • Synthesis and circular dichroism of (5S)-1-azabicyclo[3.2.0]heptan-7-one
    • Busson, R.; Vanderhaeghe, H. Synthesis and circular dichroism of (5S)-1-azabicyclo[3.2.0]heptan-7-one. J. Org. Chem., 1978, 43, 4438-4441.
    • (1978) J. Org. Chem , vol.43 , pp. 4438-4441
    • Busson, R.1    Vanderhaeghe, H.2
  • 49
    • 0001763401 scopus 로고
    • Chiroptical properties of 1-carbapenam and orbital mixing in nonplanar amides
    • Boyd, D. B.; Riehl, J. P.; Richardson, F. S. Chiroptical properties of 1-carbapenam and orbital mixing in nonplanar amides. Tetrahedron, 1979, 35, 1499-1508.
    • (1979) Tetrahedron , vol.35 , pp. 1499-1508
    • Boyd, D.B.1    Riehl, J.P.2    Richardson, F.S.3
  • 50
    • 0020639042 scopus 로고
    • A new clavam antibiotic from streptomyces clavuligerus III. Absolute stereochemistry
    • Müller, J.-C.; Toome, V.L.; Pruess, D.; Blount, J. F.; Weigele, M. A new clavam antibiotic from streptomyces clavuligerus III. Absolute stereochemistry. J. Antibiot., 1983, 36, 217-225.
    • (1983) J. Antibiot , vol.36 , pp. 217-225
    • Müller, J.-C.1    Toome, V.L.2    Pruess, D.3    Blount, J.F.4    Weigele, M.5
  • 51
    • 0037040683 scopus 로고    scopus 로고
    • Frelek 5-Dethia-5-oxacephams: Toward correlation of absolute configuration and chiroptical properties
    • Łysek, R.; Borsuk, K.; Chmielewski, M.; Kałuz̈a, Z.; Urba Czyk-Lipkowska, Z.; Klimek, A.; J., Frelek 5-Dethia-5-oxacephams: Toward correlation of absolute configuration and chiroptical properties. J. Org. Chem., 2002, 67, 1472-1479.
    • (2002) J. Org. Chem , vol.67 , pp. 1472-1479
    • Łsek, R.1    Borsuk, K.2    Chmielewski, M.3    Kałuz̈a, Z.4    Urba Czyk-Lipkowska, Z.5    Klimek, A.J.6
  • 53
    • 43249086215 scopus 로고    scopus 로고
    • Structure - chiroptical properties relationship in clavams: An experimental and theoretical study
    • Chmielewski, M.; Cierpucha, M.; Kowalska, P.; Kwit, M.; Frelek, J. Structure - chiroptical properties relationship in clavams: an experimental and theoretical study. Chirality, 2008, 20, 621-627.
    • (2008) Chirality , vol.20 , pp. 621-627
    • Chmielewski, M.1    Cierpucha, M.2    Kowalska, P.3    Kwit, M.4    Frelek, J.5
  • 55
    • 65249086428 scopus 로고    scopus 로고
    • Excited states from time-dependent density functional theory
    • Elliot, P.; Furche, F.; Burke, K. Excited states from time-dependent density functional theory. Rev. Comp. Chem., 2009, 26, 91-165.
    • (2009) Rev. Comp. Chem , vol.26 , pp. 91-165
    • Elliot, P.1    Furche, F.2    Burke, K.3
  • 57
    • 85196231922 scopus 로고    scopus 로고
    • CaChe WS Pro 5.0. Fujitsu Ltd
    • CaChe WS Pro 5.0. Fujitsu Ltd.
  • 58
    • 26344435738 scopus 로고
    • Fully optimized contracted Gaussian basis sets for atoms Li to Kr
    • Schäfer, A.; Horn, H.; Ahlrichs, R. Fully optimized contracted Gaussian basis sets for atoms Li to Kr. J. Chem. Phys., 1992, 97, 2571-2577.
    • (1992) J. Chem. Phys , vol.97 , pp. 2571-2577
    • Schäfer, A.1    Horn, H.2    Ahlrichs, R.3
  • 59
    • 0001322105 scopus 로고    scopus 로고
    • Rationale for mixing exact exchange with density functional approximations
    • Perdew, J.P.; Ernzerhof, M.; Burke, K. Rationale for mixing exact exchange with density functional approximations. J. Chem. Phys., 1996, 105, 9982-9985.
    • (1996) J. Chem. Phys , vol.105 , pp. 9982-9985
    • Perdew, J.P.1    Ernzerhof, M.2    Burke, K.3
  • 60
    • 4243539377 scopus 로고
    • Electronic structure calculations on workstation computers: The program system turbomole
    • Ahlrichs, R.; Bär, M.; Häser, M.; Horn, H.; Kölmel, C. Electronic structure calculations on workstation computers: The program system turbomole. Chem. Phys. Lett., 1989, 162, 165-169.
    • (1989) Chem. Phys. Lett , vol.162 , pp. 165-169
    • Ahlrichs, R.1    Bär, M.2    Häser, M.3    Horn, H.4    Kölmel, C.5


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