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3-Amino-5-hydroxybenzoic acid as a key intermediate in ansamycin and maytansinoid biosynthesis
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0019365586
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A genetic approach to the biosynthesis of the rifamycin chromophore in Nocardia mediterranei. IV. Identification of 3-amino-5-hydroxybenzoic acid as a direct precursor of the seven-carbon amino starter unit
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Ghisalba O Nüesch J A genetic approach to the biosynthesis of the rifamycin chromophore in Nocardia mediterranei. IV. Identification of 3-amino-5-hydroxybenzoic acid as a direct precursor of the seven-carbon amino starter unit. J Antibiot. 34:1981;64-71.
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7N units in ansamycin antibiotics. J Am Chem Soc. 118:1996;7486-7491.
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Kim, C.-G.1
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Ning, S.7
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9
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0032513247
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7N units in rifamycin and related antibiotics
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This paper describes the purification, cloning, heterologous expression and mechanistic analysis of AHBA synthase, the key enzyme for the synthesis of the rifamycin polyketide starter unit
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7N units in rifamycin and related antibiotics. J Biol Chem. 273:1998;6030-6040. This paper describes the purification, cloning, heterologous expression and mechanistic analysis of AHBA synthase, the key enzyme for the synthesis of the rifamycin polyketide starter unit.
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Kim, C.-G.1
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10
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0033520088
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The crystal structure of 3-amino-5-hydroxybenzoic acid (AHBA) synthase
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This paper reports the X-ray crystal structures of AHBA synthase holoenzyme and an enzyme-inhibitor complex
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Eads JC, Beeby M, Scapin G, Yu T-W, Floss HG The crystal structure of 3-amino-5-hydroxybenzoic acid (AHBA) synthase. Biochemistry. 38:1999;9840-9849. This paper reports the X-ray crystal structures of AHBA synthase holoenzyme and an enzyme-inhibitor complex.
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Eads, J.C.1
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11
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Biosynthesis of 3,6-dideoxyhexoses: New mechanistic reflection upon 2,6-dideoxy, 4,6-dideoxy, and amino sugar construction
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Thorson JS, Lo SF, Liu H-w, Hutchinson CR Biosynthesis of 3,6-dideoxyhexoses: new mechanistic reflection upon 2,6-dideoxy, 4,6-dideoxy, and amino sugar construction. J Am Chem Soc. 115:1993;6993-6994.
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Piepersberg W Pathway engineering in secondary metabolite-producing actinomycetes. Crit Rev Biotechnol. 14:1994;251-285.
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Liu H-w, Thorson JS Pathways and mechanisms in the biogenesis of novel deoxysugars by bacteria. Annu Rev Microbiol. 48:1994;223-256.
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Identification of stsC, the gene encoding the L-glutamine:scyllo-inosose aminotransferase from streptomycin-producing Streptomycetes
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Ahlert J, Diestler J, Mansouri K, Piepersberg W Identification of stsC, the gene encoding the L-glutamine:scyllo-inosose aminotransferase from streptomycin-producing Streptomycetes. Arch Microbiol. 168:1997;102-113.
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15
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0032584941
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Characterization of the enzymatic domains in the modular polyketide synthase involved in rifamycin B biosynthesis by Amycolatopsis mediterranei
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A detailed discussion of the sequence analysis of the rifamycin PKS and of the functions of its various domains deduced from sequence comparisons
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Tang L, Yoon YJ, Choi CY, Hutchinson CR Characterization of the enzymatic domains in the modular polyketide synthase involved in rifamycin B biosynthesis by Amycolatopsis mediterranei. Gene. 216:1998;255-265. A detailed discussion of the sequence analysis of the rifamycin PKS and of the functions of its various domains deduced from sequence comparisons.
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Tang, L.1
Yoon, Y.J.2
Choi, C.Y.3
Hutchinson, C.R.4
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16
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0032519914
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Cloning and sequence analysis of the putative rifamycin polyketide synthase gene cluster from Amycolatopsis mediterranei
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This paper reports the sequence analysis of the rifamycin PKS and discusses its functions based on sequence comparisons
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Schupp T, Toupet C, Engel N, Goff S Cloning and sequence analysis of the putative rifamycin polyketide synthase gene cluster from Amycolatopsis mediterranei. FEMS Microbiol Lett. 159:1998;201-207. This paper reports the sequence analysis of the rifamycin PKS and discusses its functions based on sequence comparisons.
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Schupp, T.1
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Engel, N.3
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17
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13144258781
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Biosynthesis of the ansamycin antibiotic rifamycin: Deductions from the molecular analysis of the rif biosynthetic gene cluster of Amycolatopsis mediterranei S699
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This paper reports the sequence of the entire rifamycin biosynthesis gene cluster and deduced functions for many of the genes
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August PR, Tang L, Yoon YJ, Ning S, Müller R, Yu T-W, Taylor M, Hoffmann D, Kim C-G, Zhang Xet al. Biosynthesis of the ansamycin antibiotic rifamycin: deductions from the molecular analysis of the rif biosynthetic gene cluster of Amycolatopsis mediterranei S699. Chem Biol. 5:1998;69-79. This paper reports the sequence of the entire rifamycin biosynthesis gene cluster and deduced functions for many of the genes.
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Chem Biol
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August, P.R.1
Tang, L.2
Yoon, Y.J.3
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Müller, R.5
Yu, T.-W.6
Taylor, M.7
Hoffmann, D.8
Kim, C.-G.9
Zhang, X.10
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19
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0032506939
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Primer unit specificity in rifamycin biosynthesis principally resides in the later stages of the biosynthetic pathway
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This paper shows that the rifamycin PKS can be primed with false starter units, but subsequently recognizes and prematurely releases the aberrant polyketide intermediates
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Hunziker D, Yu T-W, Hutchinson CR, Floss HG, Khosla C Primer unit specificity in rifamycin biosynthesis principally resides in the later stages of the biosynthetic pathway. J Am Chem Soc. 120:1998;1092-1098. This paper shows that the rifamycin PKS can be primed with false starter units, but subsequently recognizes and prematurely releases the aberrant polyketide intermediates.
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J Am Chem Soc
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Hunziker, D.1
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Khosla, C.5
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20
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0020460347
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A genetic approach to the biosynthesis of the rifamycin-chromophore in Nocardia mediterranei. V. Studies on the biogenetic origin of 3-substituents
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Traxler P, Ghisalba O A genetic approach to the biosynthesis of the rifamycin-chromophore in Nocardia mediterranei. V. Studies on the biogenetic origin of 3-substituents. J Antibiot. 35:1982;1361-1366.
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0019352851
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A genetic approach to the biosynthesis of the rifamycin-chromophore in Nocardia mediterranei. III. Isolation and idntification of an early aromatic ansamycin-precursor containing the seven-carbon amino starter-unit and three initial acetate/propionate-units of the ansa chain
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Ghisalba O, Fuhrer H, Richter WJ, Moss S A genetic approach to the biosynthesis of the rifamycin-chromophore in Nocardia mediterranei. III. Isolation and idntification of an early aromatic ansamycin-precursor containing the seven-carbon amino starter-unit and three initial acetate/propionate-units of the ansa chain. J Antibiot. 34:1981;58-63.
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22
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0030875774
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Precursor-directed biosynthesis of erythromycin analogs by an engineered polyketide synthase
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Jacobsen JR, Hutchinson CR, Cane DE, Khosla C Precursor-directed biosynthesis of erythromycin analogs by an engineered polyketide synthase. Science. 277:1997;367-369.
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Khosla, C.4
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23
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0033529935
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Direct evidence that the rifamycin polyketide synthase assembles polyketide chains processively
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This paper demonstrates a new polyketide release mechanism for the rifamycin PKS and shows that the enzyme sheds incompletely assembled linear polyketides
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Yu T-W, Shen Y, Doi-Katayama Y, Tang L, Park C, Moore BS, Hutchinson CR, Floss HG Direct evidence that the rifamycin polyketide synthase assembles polyketide chains processively. Proc Natl Acad Sci USA. 96:1999;9051-9056. This paper demonstrates a new polyketide release mechanism for the rifamycin PKS and shows that the enzyme sheds incompletely assembled linear polyketides.
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Proc Natl Acad Sci USA
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Yu, T.-W.1
Shen, Y.2
Doi-Katayama, Y.3
Tang, L.4
Park, C.5
Moore, B.S.6
Hutchinson, C.R.7
Floss, H.G.8
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24
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0033079834
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Mechanism and specificity of the terminal thioesterase domain from the erythromycin polyketide synthase
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This paper sheds light on the function of the terminal thioesterase domain of the erythromycin PKS, suggesting that macrolactone formation requires the combined action of the thioesterase and another domain of the PKS
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Gokhale RS, Hunziker D, Cane DE, Khosla C Mechanism and specificity of the terminal thioesterase domain from the erythromycin polyketide synthase. Chem Biol. 6:1999;117-125. This paper sheds light on the function of the terminal thioesterase domain of the erythromycin PKS, suggesting that macrolactone formation requires the combined action of the thioesterase and another domain of the PKS.
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Chem Biol
, vol.6
, pp. 117-125
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Gokhale, R.S.1
Hunziker, D.2
Cane, D.E.3
Khosla, C.4
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25
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0028236752
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Analysis of five tylosin biosynthetic genes from the tyllBA region of the Streptomyces fradiae genome
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Merson-Davies LA, Cundliffe E Analysis of five tylosin biosynthetic genes from the tyllBA region of the Streptomyces fradiae genome. Mol Microbiol. 13:1994;349-355.
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26
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0032514668
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A gene cluster for macrolide antibiotic biosynthesis in Streptomyces venezuelae: Architecture of metabolic diversity
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This paper reports the biosynthetic gene cluster for the 12-membered macrolides methymycin/neomethymycin and the 14-membered macrolides narbomycin/pikromycin and demonstrates that both types of macrolides are synthesized on the same PKS
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Xue Y, Zhao L, Liu H-w, Sherman DH A gene cluster for macrolide antibiotic biosynthesis in Streptomyces venezuelae: architecture of metabolic diversity. Proc Natl Acad Sci USA. 95:1998;12111-12116. This paper reports the biosynthetic gene cluster for the 12-membered macrolides methymycin/neomethymycin and the 14-membered macrolides narbomycin/pikromycin and demonstrates that both types of macrolides are synthesized on the same PKS.
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Proc Natl Acad Sci USA
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, pp. 12111-12116
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Xue, Y.1
Zhao, L.2
Liu, H.-W.3
Sherman, D.H.4
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27
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0031943369
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Genetic evidence for a role of thioesterase domains, integrated in or associated with peptide synthetases, in non-ribosomal peptide biosynthesis in Bacillus subtilis
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This paper demonstrates the essential role of two peptide synthase-associated thioesterases in the formation of the peptide antibiotic surfactin
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Schneider A, Marahiel MA Genetic evidence for a role of thioesterase domains, integrated in or associated with peptide synthetases, in non-ribosomal peptide biosynthesis in Bacillus subtilis. Arch Microbiol. 169:1998;404-410. This paper demonstrates the essential role of two peptide synthase-associated thioesterases in the formation of the peptide antibiotic surfactin.
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Arch Microbiol
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, pp. 404-410
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Schneider, A.1
Marahiel, M.A.2
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28
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0008845004
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Bio-organic chemistry of ansamycin and mitomycin antibiotics
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Edited by Atta-ur-Rahman. Amsterdam: Elsevier Science Ltd.
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Rickards RW: Bio-organic chemistry of ansamycin and mitomycin antibiotics. In Studies in Natural Products Chemistry, vol 9. Edited by Atta-ur-Rahman. Amsterdam: Elsevier Science Ltd. 1991:431-445.
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0018240314
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Early intermediates in the biosynthesis of ansamycins. I. Isolation and identification of protorifamycin I
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Ghisalba O, Traxler P, Nüesch J Early intermediates in the biosynthesis of ansamycins. I. Isolation and identification of protorifamycin I. J Antibiot. 31:1978;1124-1131.
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0024595910
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Biosynthetic origins of the oxygen atoms in the ansamycin antibiotics rifamycin B, O and S
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Anderson MG, Monypenny D, Rickards RW, Rothschild JM Biosynthetic origins of the oxygen atoms in the ansamycin antibiotics rifamycin B, O and S. J Chem Soc Chem Commun. 1989;11-313.
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J Chem Soc Chem Commun
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Anderson, M.G.1
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Rickards, R.W.3
Rothschild, J.M.4
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