Volume 15, Issue 7, Pages (July 2008)

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Volume 15, Issue 7, Pages 693-705 (July 2008) Characterization of the Azinomycin B Biosynthetic Gene Cluster Revealing a Different Iterative Type I Polyketide Synthase for Naphthoate Biosynthesis Qunfei Zhao, Qingli He, Wei Ding, Mancheng Tang, Qianjin Kang, Yi Yu, Wei Deng, Qi Zhang, Jie Fang, Gongli Tang, Wen Liu Chemistry & Biology Volume 15, Issue 7, Pages 693-705 (July 2008) DOI: 10.1016/j.chembiol.2008.05.021 Copyright © 2008 Elsevier Ltd Terms and Conditions

Figure 1 Natural Products Containing an Aromatic Moiety Structures of azinomycins (A and B), neocarzinostatin, cholorothricin, maduropeptin, avilamycin and calicheamicin that bear a biocyclic or monocyclic aromatic polyketide moiety in each. Chemistry & Biology 2008 15, 693-705DOI: (10.1016/j.chembiol.2008.05.021) Copyright © 2008 Elsevier Ltd Terms and Conditions

Figure 2 Cloned DNA Region on the Chromosome of S. sahachiroi and Restriction Map and Genetic Organization of the azi Biosynthetic Gene Cluster (A) An 80 kb contiguous DNA locus represented by five cosmids and restriction map. Solid black bars indicate regions whose sequence has been determined. Solid quadrates indicate the probe loci. B, BamHI. (B) Genetic organization of the azi gene cluster. Proposed functions of individual orfs are labeled and summarized in Table 1. Chemistry & Biology 2008 15, 693-705DOI: (10.1016/j.chembiol.2008.05.021) Copyright © 2008 Elsevier Ltd Terms and Conditions

Figure 3 Proposed Biosynthetic Pathway of Azinomycin B (A–C) Pathways for building blocks (A) 3-methoxy-5-methyl-NPA (1); (B) α-ketoisovaleric acid (2); and (C) aziridino[1, 2a]pyrrolidinyl amino acid (3). (D) A mode for NRPS-directed skeleton assembly and tailoring modifications. Chemistry & Biology 2008 15, 693-705DOI: (10.1016/j.chembiol.2008.05.021) Copyright © 2008 Elsevier Ltd Terms and Conditions

Figure 4 Functional Validation of Genes Involved in Azinomycin B Biosynthesis (A) Determination of azinomycin B production by assaying the antibacterial activity against M. luteus. 1, S. sahachiroi wild-type strain; 2, AL1001; 3, AL1002; and 4, AL1003. (B) HPLC analysis of azinomycin B (solid asterisk) isolated from wild-type strain (I); AL1001 (II); AL1002 (III); and AL1003 (IV). Chemistry & Biology 2008 15, 693-705DOI: (10.1016/j.chembiol.2008.05.021) Copyright © 2008 Elsevier Ltd Terms and Conditions

Figure 5 Establishment of the Naphthoate Pathway HPLC analysis of 5-methyl-NPA (solid triangle) and 3-methoxy-5-methyl-NPA (solid dot) production in the heterologous host S. albus. I, AL1006; II, AL1004; III, AL1007; IV, Al1008; V, AL1009; VI, 3-methoxy-5-methyl-NPA standard; and VII, AL1005. Chemistry & Biology 2008 15, 693-705DOI: (10.1016/j.chembiol.2008.05.021) Copyright © 2008 Elsevier Ltd Terms and Conditions

Figure 6 Iterative Type I PKSs for Aromatic Polyketide Biosynthesis in Bacteria I, AviM and CalO5 for OSA biosynthesis; II, ChlB1 and MadB for 6-MSA biosynthesis; III, NcsB for 2-hydroxy-5-methyl-NPA biosynthesis; and IV, AziB for 5-methyl-NPA biosynthesis. Chemistry & Biology 2008 15, 693-705DOI: (10.1016/j.chembiol.2008.05.021) Copyright © 2008 Elsevier Ltd Terms and Conditions