Biosynthesis of the Antitumor Chromomycin A3 in Streptomyces griseus

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Presentation transcript:

Biosynthesis of the Antitumor Chromomycin A3 in Streptomyces griseus Nuria Menéndez, Mohammad Nur-e-Alam, Alfredo F. Braña, Jürgen Rohr, José A. Salas, Carmen Méndez Chemistry & Biology Volume 11, Issue 1, Pages 21-32 (January 2004) DOI: 10.1016/j.chembiol.2003.12.011

Figure 1 Structure of Chromomycin A3 and Derivatives and Genetic Organization of the Chromomycin and Mithramycin Gene Clusters (A) Chemical structures of chromomycin A3 and its new derivatives generating by insertional inactivation: chromomycin A3 (1), chromomycin SA (2), chromomycin SK (3), and chromomycin SDK (4). The stereochemistry of C-2′ in chromomycin SK was deduced from its NMR data in comparison with its analog mithramycin SK (see [12]). (B) Genetic organization of the chromomycin A3 gene cluster and its comparison with the mithramycin gene cluster. Chemistry & Biology 2004 11, 21-32DOI: (10.1016/j.chembiol.2003.12.011)

Figure 2 Generation and Analysis of Mutant C60WI (A) Scheme representing the replacement in the chromosome of the wild-type cmmWI gene by the in vitro mutated one. aac(3)IV, apramycin-resistance gene; tsr, thiostrepton-resistance gene; bla, β-lactamase gene. (B) Southern hybridization using the 9.6 kb PstI fragment as probe. Lane 1, PstI-digested chromosomal DNA from mutant C60WI; lane 2, PstI-digested chromosomal DNA from wild-type strain. (C) HPLC analysis of a culture of mutant C60WI. Chemistry & Biology 2004 11, 21-32DOI: (10.1016/j.chembiol.2003.12.011)

Figure 3 Formation of Chromomycin Derivatives Formation of chromomycins SK (3) and SDK (4) through a Favorskii-like rearrangement and of chromomycin SA (2) through retro-aldol-type cleavage of the reactive product 5, proposed to be generated by the inactivation of the ketoreductase-encoding gene cmmWI. Chemistry & Biology 2004 11, 21-32DOI: (10.1016/j.chembiol.2003.12.011)

Figure 4 Proposed Pathway for the Biosynthesis of Chromomycin A3 Chemistry & Biology 2004 11, 21-32DOI: (10.1016/j.chembiol.2003.12.011)

Figure 5 Proposed Pathways for the Biosynthesis of the Deoxysugars in Chromomycin A3 Chemistry & Biology 2004 11, 21-32DOI: (10.1016/j.chembiol.2003.12.011)