Chemistry and biosynthesis of clavulanic acid and other clavams

Natural Product Reports - Tập 14 Số 4 - Trang 309 - 1997
Keith H. Baggaley1, A. G. BROWN, Christopher J. Schofield
1Dyson Perrins Laboratory, University of Oxford UK

Tóm tắt

Từ khóa


Tài liệu tham khảo

Nagarajan, 1971, J. Am. Chem. Soc., 93, 2308, 10.1021/ja00738a035

Brown, 1976, J. Antibiot., 29, 668, 10.7164/antibiotics.29.668

Slocombe, 1984, Postgrad. Med., 76, 29

Sutherland, 1985, Am. J. Med., 79, 13, 10.1016/0002-9343(85)90124-X

Brown, 1986, Drug Des. Delivery, 1, 1

Abraham, 1940, Nature, 146, 837, 10.1038/146837a0

Rolinson, 1979, J. Antimicrob. Chemother., 5, 7, 10.1093/jac/5.1.7

Abraham, 1961, Biochem. J., 79, 377, 10.1042/bj0790377

Hodgkin, 1961, Biochem. J., 79, 393, 10.1042/bj0790393

Sutherland, 1991, Tends Pharmacol. Sci., 12, 227, 10.1016/0165-6147(91)90557-9

Richmond, 1973, Adv. Microb. Physiol., 9, 31, 10.1016/S0065-2911(08)60376-8

Sykes, 1976, J. Antimicrob. Chemother., 2, 115, 10.1093/jac/2.2.115

Bush, 1989, Antimicrob. Agents Chemother., 33, 259, 10.1128/AAC.33.3.259

Bush, 1989, Antimicrob. Agents Chemother., 33, 264, 10.1128/AAC.33.3.264

Bush, 1989, Antimicrob. Agents Chemother., 33, 271, 10.1128/AAC.33.3.271

Ambler, 1980, Philos. Trans. R. Soc. London, B, 289, 321, 10.1098/rstb.1980.0049

Rawlings, 1994, Methods Enzymol., 244, 19, 10.1016/0076-6879(94)44004-2

Matagne, 1995, Biochem. Biophys. Acta, 1246, 109, 10.1016/0167-4838(94)00177-I

Ledent, 1993, Biochem. J., 292, 555, 10.1042/bj2920555

Nue, 1985, Am. J. Med., 79, 2

Möellering, Jr., 1991, Rev. Infect. Dis., 13, S723, 10.1093/clinids/13.Supplement_9.S723

Stapley, 1972, Antimicrob. Agents Chemother., 2, 122, 10.1128/AAC.2.3.122

Miller, 1972, Antimicrob. Agents Chemother., 2, 132, 10.1128/AAC.2.3.132

Albers-Schönberg, 1972, Tetrahedron Lett., 2911, 10.1016/S0040-4039(01)84970-4

Reading, 1977, Antimicrob. Agents Chemother., 11, 122, 10.1128/AAC.11.5.852

Howarth, 1976, J. Chem. Soc., Chem. Commun., 266, 10.1039/C3976000266B

Brown, 1977, J. Chem. Soc., Chem. Commun., 523, 10.1039/C39770000523

Butterworth, 1979, J. Antibiot., 32, 287, 10.7164/antibiotics.32.287

Hood, 1979, J. Antibiot., 32, 295, 10.7164/antibiotics.32.295

Corbett, 1977, J. Chem. Soc., Chem. Commun., 953, 10.1039/C39770000953

Box, 1979, J. Antibiot., 32, 1239, 10.7164/antibiotics.32.1239

Kahan, 1979, J. Antibiot., 32, 1, 10.7164/antibiotics.32.1

Albers-Schönberg, 1978, J. Am. Chem. Soc., 100, 6491, 10.1021/ja00488a038

Stapley, 1981, J. Antibiot., 34, 628, 10.7164/antibiotics.34.628

Cassidy, 1981, J. Antibiot., 34, 637, 10.7164/antibiotics.34.637

Brown, 1981, J. Antimicrob. Chemother., 7, 15, 10.1093/jac/7.1.15

Southgate, 1985, Prog. Chem. Org. Nat. Prod., 47, 1

Hashimoto, 1976, J. Am. Chem. Soc., 98, 3023, 10.1021/ja00426a063

Imada, 1981, Nature, 289, 590, 10.1038/289590a0

Sykes, 1981, Nature, 291, 489, 10.1038/291489a0

Singh, 1984, J. Antibiot., 37, 773, 10.7164/antibiotics.37.773

Shoji, 1984, J. Antibiot., 37, 1486, 10.7164/antibiotics.37.1486

Ono, 1984, J. Antibiot., 37, 1528, 10.7164/antibiotics.37.1528

Coleman, 1989, Antimicrob. Agents Chemother., 33, 1580, 10.1128/AAC.33.9.1580

Hunter, 1980, J. Antimicrob. Chemother., 6, 455, 10.1093/jac/6.4.455

Hunter, 1978, Current Chemotherapy, 1, 478

Spratt, 1977, Antimicrob. Agents Chemother., 12, 406, 10.1128/AAC.12.3.406

Jackson, 1984, Postgrad. Med., 76, 51

Jackson, 1985, Am. J. Med., 79, 44, 10.1016/0002-9343(85)90128-7

Mizen, 1981, Drugs Exp. Clin. Res., 7, 263

Hunter, 1984, Pharm. Weekbl., 119, 650

Elson, 1987, J. Chem. Soc., Chem. Commun., 1736, 10.1039/C39870001736

Elson, 1988, J. Chem. Soc., Chem. Commun., 979, 10.1039/c39880000979

Brown, 1979, J. Chem. Soc., Chem. Commun., 282, 10.1039/C39790000282

Pruess, 1983, J. Antibiot., 36, 208, 10.7164/antibiotics.36.208

Evans, 1983, J. Antibiot., 36, 213, 10.7164/antibiotics.36.213

Warming, 1981, Tetrahedron Lett., 22, 2539, 10.1016/S0040-4039(01)90514-3

Postels, 1992, Liebigs Ann. Chem., 1281, 10.1002/jlac.1992199201212

Baldwin, 1993, Tetrahedron Lett., 34, 5645, 10.1016/S0040-4039(00)73905-0

Naegeli, 1986, J. Antibiot., 39, 516, 10.7164/antibiotics.39.516

Tian, 1991, Zhongguo Kangshengsu Zazhi, 16, 1

Müller, 1983, J. Antibiot., 36, 217, 10.7164/antibiotics.36.217

Higgens, 1974, J. Antibiot., 27, 208, 10.7164/antibiotics.27.298

Higgens, 1971, Int. J. Syst. Bacteriol., 21, 326, 10.1099/00207713-21-4-326

Kenig, 1979, J. Antibiot., 32, 549, 10.7164/antibiotics.32.549

Doran, 1990, J. Bacteriol., 172, 4909, 10.1128/jb.172.9.4909-4918.1990

Strynadka, 1994, Nature, 368, 657, 10.1038/368657a0

Brown, 1984, J. Chem. Soc., Perkin Trans. 1, 635, 10.1039/p19840000635

Davies, 1982, Tetrahedron Lett., 23, 5089, 10.1016/S0040-4039(00)85580-X

Brooks, 1983, J. Chem. Soc., Perkin Trans. 1, 2513, 10.1039/p19830002513

Hunt, 1981, J. Chem. Res. (S), 64

Corbett, 1977, J. Chem. Soc., Chem. Commun., 808, 10.1039/c3977000808a

Gilpin, 1981, J. Chem. Soc., Chem. Commun., 929, 10.1039/C39810000929

Brown, 1983, Tetrahedron Lett., 24, 2693, 10.1016/S0040-4039(00)87979-4

Finn, 1984, J. Chem. Soc., Perkin Trans. 1, 1345, 10.1039/p19840001345

Bolton, 1986, Xenobiotica, 16, 853, 10.3109/00498258609038967

Brooks, 1984, J. Chem. Soc., Perkin Trans. 1, 1599, 10.1039/p19840001599

Brooks, 1983, J. Chem. Soc., Perkin Trans. 1, 115, 10.1039/P19830000115

Bentley, 1977, J. Chem. Soc., Chem. Commun., 748, 10.1039/C39770000748

Bentley, 1979, Tetrahedron Lett., 20, 1889, 10.1016/S0040-4039(01)86869-6

Hunter, 1984, Pharm. Weekbl., 119, 650

English, 1978, Antimicrob. Agents Chemother., 14, 414, 10.1128/AAC.14.3.414

Campoli-Richards, 1987, Drugs, 33, 577, 10.2165/00003495-198733060-00003

Batlzer, 1980, J. Antibiot., 33, 1183, 10.7164/antibiotics.33.1183

Rogers, 1983, J. Antimicrob. Chemother., 11, 435, 10.1093/jac/11.5.435

von Daehne, 1980, J. Antibiot., 33, 451, 10.7164/antibiotics.33.451

Wise, 1981, J. Antimicrob. Chemother., 7, 531, 10.1093/jac/7.5.531

Cartwright, 1979, Nature, 278, 360, 10.1038/278360a0

Gottstein, 1981, J. Med. Chem., 24, 1531, 10.1021/jm00144a034

Keith, 1983, Tetrahedron, 39, 2445, 10.1016/S0040-4020(01)92137-4

Micetich, 1987, J. Med. Chem., 30, 1469, 10.1021/jm00391a032

Payne, 1994, Antimicrob. Agents Chemother., 38, 767, 10.1128/AAC.38.4.767

Jacobs, 1986, Antimicrob. Agents Chemother., 29, 980, 10.1128/AAC.29.6.980

Bush, 1993, Antimicrob. Agents Chemother., 37, 858, 10.1128/AAC.37.4.851

Arisawa, 1983, Biochem. J., 209, 609, 10.1042/bj2090609

Brenner, 1985, J. Org. Chem., 50, 18, 10.1021/jo00201a004

Coleman, 1989, Antimicrob. Agents Chemother., 33, 1580, 10.1128/AAC.33.9.1580

Osborne, 1989, J. Chem. Soc., Chem. Commun., 371, 10.1039/C39890000371

Ito, 1995, Antimicrob. Agents Chemother., 39, 824, 10.1128/AAC.39.4.824

Livermore, 1992, J. Antimicrob. Chemother., 29, 609, 10.1093/jac/29.6.609

Van Hove, 1995, Tetrahedron Lett., 36, 9313, 10.1016/0040-4039(95)02028-N

Walter, 1996, Bioorg. Med. Chem. Lett., 6, 2455, 10.1016/0960-894X(96)00453-2

Reading, 1979, Biochem. J., 179, 67, 10.1042/bj1790067

Reading, 1981, Biochem. J., 199, 779, 10.1042/bj1990779

Farmer, 1982, Antimicrob. Agents Chemother., 21, 506, 10.1128/AAC.21.3.506

Knowles, 1985, Acc. Chem. Res., 18, 97, 10.1021/ar00112a001

Cartwright, 1980, Philos. Trans. R. Soc. London B, 289, 370

Rizwi, 1989, Biochem. J., 258, 205, 10.1042/bj2580205

Charnas, 1978, Biochemistry, 17, 2185, 10.1021/bi00604a025

Charnas, 1981, Biochemistry, 20, 3214, 10.1021/bi00514a035

Brenner, 1984, Biochemistry, 23, 5833, 10.1021/bi00319a024

Chen, 1992, J. Mol. Biol., 224, 1103, 10.1016/0022-2836(92)90472-V

Imtiaz, 1993, J. Am. Chem. Soc., 115, 4435, 10.1021/ja00064a003

Brown, 1996, Biochemistry, 35, 12421, 10.1021/bi961044g

Elson, 1978, J. Antibiot., 31, 586, 10.7164/antibiotics.31.586

Elson, 1982, J. Antibiot., 35, 81, 10.7164/antibiotics.35.81

Townsend, 1985, J. Am. Chem. Soc., 107, 1065, 10.1021/ja00290a056

Romero, 1986, Appl. Environ. Microbiol., 52, 892, 10.1128/AEM.52.4.892-897.1986

Townsend, 1986, J. Chem. Soc., Chem. Commun., 638, 10.1039/c39860000638

Bycroft, 1988, J. Chem. Soc., Chem. Commun., 980, 10.1039/c39880000980

Townsend, 1985, J. Am. Chem. Soc., 107, 1066, 10.1021/ja00290a057

Townsend, 1987, J. Chem. Soc., Chem. Commun., 86, 10.1039/C39870000086

Sobolov, 1960, J. Bacteriol., 79, 261, 10.1128/JB.79.2.261-266.1960

Sliniger, 1983, Appl. Environ. Microbiol., 46, 892

Gutman, 1985, J. Chem. Soc., Chem. Commun., 1627, 10.1039/C39850001627

Gutman, 1986, J. Chem. Soc., Perkin Trans. 1, 521, 10.1039/P19860000521

Baldwin, 1988, Nat. Prod. Rep., 5, 129, 10.1039/np9880500129

Basak, 1990, J. Am. Chem. Soc., 112, 1654, 10.1021/ja00160a069

Robinson, 1985, Nat. Prod. Rep., 2, 293, 10.1039/NP9850200293

Bird, 1982, Analyst (London), 107, 1241, 10.1039/an9820701241

Elson, 1987, J. Chem. Soc., Chem. Commun., 1738

Baggaley, 1990, J. Chem. Soc., Perkin Trans. 1, 1513, 10.1039/P19900001513

Elson, 1987, J. Chem. Soc., Chem. Commun., 1739, 10.1039/c39870001739

Bailey, 1984, Biol/Technology, 2, 808

Hodgson, 1990, Chem. Abstr., 113, 18957d

Lawlor, 1994, Tetrahedron, 50, 8737, 10.1016/S0040-4020(01)85347-3

Ward, 1993, FEMS Microbiol. Lett., 110, 239, 10.1111/j.1574-6968.1993.tb06326.x

Hodgson, 1995, Gene, 166, 49, 10.1016/0378-1119(95)00560-9

Baggaley, 1988, J. Chem. Soc., Chem. Commun., 567, 10.1039/c39880000567

Baggaley, 1990, J. Chem. Soc., Perkin Trans. 1, 1521, 10.1039/p19900001521

Krol, 1991, J. Org. Chem., 56, 728, 10.1021/jo00002a045

Townsend, 1988, J. Chem. Soc., Chem. Commun., 1234, 10.1039/c39880001234

Nicholson, 1994, J. Chem. Soc., Chem. Commun., 1281, 10.1039/c39940001281

Gutman, 1988, Synth. Commun., 18, 1311, 10.1080/00397918808060925

Negro, 1991, Synth. Commun., 21, 359, 10.1080/00397919108016757

Jung, 1993, Chem. Abstr., 118, 80667r

Krol, 1989, J. Am. Chem. Soc., 111, 7625, 10.1021/ja00201a060

Townsend, 1991, Tetrahedron, 47, 2591, 10.1016/S0040-4020(01)81792-0

Baldwin, 1990, J. Chem. Soc., Chem. Commun., 617, 10.1039/c39900000617

Baldwin, 1991, Tetrahedron, 24, 4089, 10.1016/S0040-4020(01)86446-2

Zhang, 1995, Biochem. J., 307, 77, 10.1042/bj3070077

Hanauske-Abel, 1982, J. Theoret. Biol., 94, 421, 10.1016/0022-5193(82)90320-4

Siegel, 1979, Bioorg. Chem., 8, 219, 10.1016/0045-2068(79)90007-5

Salowe, 1990, Biochemistry, 29, 6499, 10.1021/bi00479a023

Salowe, 1991, Biochemistry, 30, 2281, 10.1021/bi00222a034

Marsh, 1992, Biochemistry, 31, 12 648, 10.1021/bi00165a015

Bushy, 1995, J. Biol. Chem., 270, 4262, 10.1074/jbc.270.9.4262

Myllylä, 1992, Biochem. J., 286, 923, 10.1042/bj2860923

Lawrence, 1996, Biochem. J., 313, 185, 10.1042/bj3130185

Roach, 1995, Nature, 375, 700, 10.1038/375700a0

Paradkur, 1995, J. Bacteriol., 177, 1307, 10.1128/jb.177.5.1307-1314.1995

Martin, 1992, J. Bacteriol., 174, 2694, 10.1128/jb.174.8.2694-2701.1992

Ludovic, 1992, J. Bacteriol., 174, 4606, 10.1128/jb.174.14.4606-4613.1992

Baldwin, 1994, J. Chem. Soc., Chem. Commun., 1133, 10.1039/c39940001133

Schroepfer, Jr., 1965, J. Biol. Chem., 240, 54, 10.1016/S0021-9258(18)97614-3

Morris, 1967, Biochem. Biophys. Res. Cummun., 28, 904, 10.1016/0006-291X(67)90064-2

Baldwin, 1993, J. Chem. Soc., Chem. Commun., 500, 10.1039/c39930000500

Baggaley, 1995, Chem. Abstr., 122, 8173s

Elson, 1993, J. Chem. Soc., Chem. Commun., 1211, 10.1039/c39930001211

Valentine, 1993, J. Chem. Soc., Chem. Commun., 1210, 10.1039/c39930001210

Elson, 1993, J. Chem. Soc., Chem. Commun., 1212, 10.1039/c39930001212

Soru, 1965, J. Chromatogr., 20, 325, 10.1016/S0021-9673(01)97418-7

Soru, 1976, Rev. Roum. Bioehim., 13, 29

Townsend, 1983, J. Am. Chem. Soc., 105, 919, 10.1021/ja00342a047

O'Sullivan, 1982, Antimicrob. Agents Chemother., 21, 558, 10.1128/AAC.21.4.558

Kutcha, 1985, J. Biol. Chem., 260, 13181, 10.1016/S0021-9258(17)38854-3

Vagelos, 1959, J. Biol. Chem., 234, 2272, 10.1016/S0021-9258(18)69797-2

Thompson, 1991, Adv. Enzymol. Relat. Areas Mol. Biol., 64, 317

McIlwaine, 1993, J. Chem. Soc., Chem. Commun., 1346, 10.1039/C39930001346

Baldwin, 1993, J. Chem. Soc., Chem. Commun., 1301, 10.1039/c39930001301

Townsend, 1984, J. Chem. Soc., Chem. Commun., 1586, 10.1039/C39840001586

Townsend, 1985, J. Nat. Prod., 48, 708, 10.1021/np50041a002

Englard, 1985, Biochemistry, 24, 1110, 10.1021/bi00326a007

Stubbe, 1985, J. Biol. Chem., 260, 9972, 10.1016/S0021-9258(17)39197-4

Baldwin, 1992, J. Chem. Soc., Chem. Commun., 877, 10.1039/C39920000877

Baldwin, 1993, J. Chem. Soc., Chem. Commun., 1694, 10.1039/c39930001694

Martinkus, 1983, Tetrahedron, 39, 3493, 10.1016/S0040-4020(01)88659-2

Kawauchi, 1983, Int. Peptide Protein Res., 21, 54

Elson, 1992, Bioorg. Med. Chem Lett., 2, 1503, 10.1016/S0960-894X(00)80417-5

Iwata-Reuyl, 1993, J. Nat. Prod., 56, 1373, 10.1021/np50098a022

Aidoo, 1994, Gene, 147, 41, 10.1016/0378-1119(94)90036-1

Wu, 1995, J. Bacteriol., 177, 3714, 10.1128/jb.177.13.3714-3720.1995

Prescot, 1993, J. Expt. Bot., 44, 849, 10.1093/jxb/44.5.849

Baker, 1990, FASEB J., 4, 222, 10.1096/fasebj.4.2.2153594

Iwata-Reuyl, 1992, J. Am. Chem. Soc., 114, 2762, 10.1021/ja00033a086

Janc, 1993, Bioorg. Med. Chem. Lett., 2313, 10.1016/S0960-894X(01)80946-X

Baldwin, 1994, Tetrahedron Lett., 35, 2779, 10.1016/S0040-4039(00)77031-6

Baldwin, 1994, Tetrahedron Lett., 35, 2783, 10.1016/S0040-4039(00)77032-8

Janc, 1995, J. Biol. Chem., 270, 5399, 10.1074/jbc.270.10.5399

Busby, 1996, Bioorg. Med. Chem., 4, 1059, 10.1016/0968-0896(96)00088-0

Pitlik, 1997, Chem. Commun., 225, 10.1039/a607078g

Thirkettle, 1997, Chem. Commun., 1025, 10.1039/a701934c

Egan, 1997, J. Am. Chem. Soc., 119, 2348, 10.1021/ja963107o