Volume 14, Issue 8, Pages (August 2007)

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Volume 14, Issue 8, Pages 955-967 (August 2007) Improved Mutasynthetic Approaches for the Production of Modified Aminocoumarin Antibiotics Christine Anderle, Susanne Hennig, Bernd Kammerer, Shu-Ming Li, Ludger Wessjohann, Bertolt Gust, Lutz Heide Chemistry & Biology Volume 14, Issue 8, Pages 955-967 (August 2007) DOI: 10.1016/j.chembiol.2007.07.014 Copyright © 2007 Elsevier Ltd Terms and Conditions

Figure 1 Aminocoumarin Antibiotics (A) Structure and biosynthesis of novobiocin. (B) Structures of simocyclinone D8, coumermycin A1, and clorobiocin. The amide bonds generated by the amide synthetases NovL, SimL, CouL, and CloL are marked in gray. Chemistry & Biology 2007 14, 955-967DOI: (10.1016/j.chembiol.2007.07.014) Copyright © 2007 Elsevier Ltd Terms and Conditions

Figure 2 Construction of clo-CA5 and Southern Blot Analysis of the Mutant S. coelicolor(clo-CA5) (A) Cosmid constructs clo-BG1 (intact) and clo-CA5 (ΔcloLΔcloQ) containing the clorobiocin biosynthetic gene cluster and the ФC31 integration functions. T3, T7 = T3, and T7 promoter of the SuperCos1 vector. The cosmid backbone is not to scale. (B) Schematic representation of site-specific integration of clo-CA5 into the S. coelicolor chromosome. B = BglII restriction site. Fragment sizes resulting from digestion with BglII are indicated. (C) Schematic presentation of the cloL and cloQ inactivation and restriction fragment analysis of the modified cosmids. cloL was replaced by an apramycin cassette that was subsequently excised by restriction enzyme digestion and religated, leaving an in-frame “scar” of 18 nucleotides, resulting in cosmid clo-CA3. In the same way, cloQ was inactivated, resulting in cosmid clo-CA5. This figure is not to scale. M = 1 kb DNA ladder (Invitrogen). DNA of clo-BG1, clo-CA3, and clo-CA5 were digested with BglII. (D) Southern blot analysis of the S. coelicolor M512 (S. c.) integration mutant harboring clo-CA5. M = DIG-labeled DNA Molecular Weight Marker VII (Roche). Genomic DNA was digested with BglII. The DIG-labeled cosmid clo-BG1 was used as a probe. Chemistry & Biology 2007 14, 955-967DOI: (10.1016/j.chembiol.2007.07.014) Copyright © 2007 Elsevier Ltd Terms and Conditions

Figure 3 HPLC Analysis of Culture Extracts (A and B) HPLC analysis of culture extracts of different S. coelicolor(clo-CA5) mutants after feeding of (A) 3,5-dimethyl-4-hydroxybenzoic acid or (B) benzoic acid. The identity of the marked peaks was confirmed by LC-MS as well as by 1H-NMR. Unmarked peaks are metabolites unrelated to aminocoumarins, as confirmed by LC-MS. Chemistry & Biology 2007 14, 955-967DOI: (10.1016/j.chembiol.2007.07.014) Copyright © 2007 Elsevier Ltd Terms and Conditions

Figure 4 Schematic of the Two-Stage Feeding Procedure See text for explanations. Chemistry & Biology 2007 14, 955-967DOI: (10.1016/j.chembiol.2007.07.014) Copyright © 2007 Elsevier Ltd Terms and Conditions