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Chapter 14 : Antibiotic Biosynthesis: Principles

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Antibiotic Biosynthesis: Principles, Page 1 of 2

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Abstract:

The prevalence of natural products as clinically useful antibiotics represents some 80 years of activity-guided isolation protocols and dereplication of known structures to enable discovery of novel molecules.

Citation: Walsh C, Wencewicz T. 2016. Antibiotic Biosynthesis: Principles, p 276-287. In Antibiotics: Challenges, Mechanisms, Opportunities. ASM Press, Washington, DC. doi: 10.1128/9781555819316.ch14
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Figures

Image of Figure 14.0
Figure 14.0

Colorful antibiotics from streptomycetes. (From Sir David Hopwood, John Innes Centre, Norwich, United Kingdom, used with permission.)

Citation: Walsh C, Wencewicz T. 2016. Antibiotic Biosynthesis: Principles, p 276-287. In Antibiotics: Challenges, Mechanisms, Opportunities. ASM Press, Washington, DC. doi: 10.1128/9781555819316.ch14
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Image of Figure 14.1
Figure 14.1

Frequency of discovery of new antibiotics as a function of the total antibiotics discovered. Stt, streptothricin; Sm, streptomycin; Tet, tetracycline, Act, actinomycin; Van, vancomycin; Ery, erythromycin; Dap, daptomycin. (Reprinted from Baltz [2007] with permission.)

Citation: Walsh C, Wencewicz T. 2016. Antibiotic Biosynthesis: Principles, p 276-287. In Antibiotics: Challenges, Mechanisms, Opportunities. ASM Press, Washington, DC. doi: 10.1128/9781555819316.ch14
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Image of Figure 14.2
Figure 14.2

(a) Five antibiotics known to be produced by —the aminoglycoside streptomycin and three polyketides: daunomycin, fredericamycin A, chromomycin A3, and a hybrid nonribosomal peptide-polyketide tetramate macrolactam. (b) Three antibiotics from : actinorhodin, undecylprodigiosin, and Ca-dependent antibiotic.

Citation: Walsh C, Wencewicz T. 2016. Antibiotic Biosynthesis: Principles, p 276-287. In Antibiotics: Challenges, Mechanisms, Opportunities. ASM Press, Washington, DC. doi: 10.1128/9781555819316.ch14
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Image of Figure 14.3
Figure 14.3

Bioinformatic analysis of the seven chromosomes of indicates 14 gene clusters for nonribosomal peptides or hybrids with polyketides (Hoffmeister and Keller, 2007). Four known metabolites are indicated here.

Citation: Walsh C, Wencewicz T. 2016. Antibiotic Biosynthesis: Principles, p 276-287. In Antibiotics: Challenges, Mechanisms, Opportunities. ASM Press, Washington, DC. doi: 10.1128/9781555819316.ch14
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Image of Vignette 14.1
Vignette 14.1

The streptomycete lantipeptide SapB is a developmental morphogen and has no antibiotic activity.

Citation: Walsh C, Wencewicz T. 2016. Antibiotic Biosynthesis: Principles, p 276-287. In Antibiotics: Challenges, Mechanisms, Opportunities. ASM Press, Washington, DC. doi: 10.1128/9781555819316.ch14
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Image of Figure 14.4
Figure 14.4

Correlation of bacterial genome size and secondary metabolite production. Donadio et al. (2007) suggested that genomes of ≤3 megabases of DNA would have little capacity for polyketides or nonribosomal peptides beyond siderophores needed for import of iron. It remains to be seen if the correlation holds when tens of thousands of additional bacterial genomes are curated. TMS, thiotemplate modular systems. (Adapted from Donadio et al. [2007] with permission.)

Citation: Walsh C, Wencewicz T. 2016. Antibiotic Biosynthesis: Principles, p 276-287. In Antibiotics: Challenges, Mechanisms, Opportunities. ASM Press, Washington, DC. doi: 10.1128/9781555819316.ch14
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Image of Figure 14.5
Figure 14.5

Novel natural product scaffolds from environmental DNA samples from uncultured organisms. The gene clusters were expressed in heterologous hosts to allow compound production and identification (Bauer et al., 2010; Biggens et al., 2012; Kallifidas et al., 2012).

Citation: Walsh C, Wencewicz T. 2016. Antibiotic Biosynthesis: Principles, p 276-287. In Antibiotics: Challenges, Mechanisms, Opportunities. ASM Press, Washington, DC. doi: 10.1128/9781555819316.ch14
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Image of Figure 14.6
Figure 14.6

Regulatory gene circuitry in : action of butyrolactone quorum inducer via a series of positive and negative regulators to control synthesis of the buytrolactone and the steps for positive regulation (red arrow) for expression of the streptomycin biosynthetic gene cluster for production and secretion of the aminoglycoside antibiotic.

Citation: Walsh C, Wencewicz T. 2016. Antibiotic Biosynthesis: Principles, p 276-287. In Antibiotics: Challenges, Mechanisms, Opportunities. ASM Press, Washington, DC. doi: 10.1128/9781555819316.ch14
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Image of Figure 14.7
Figure 14.7

Three oxidation states at C of the butanolide scaffold are recognized by cognate receptors, FarA, ArpA, and BarA, in different streptomycetes. (Reprinted from Walsh [2003] with permission.)

Citation: Walsh C, Wencewicz T. 2016. Antibiotic Biosynthesis: Principles, p 276-287. In Antibiotics: Challenges, Mechanisms, Opportunities. ASM Press, Washington, DC. doi: 10.1128/9781555819316.ch14
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Image of Figure 14.8
Figure 14.8

Biosynthesis of 6α- and 6β-hydroxybutanolide diastereomers from DHAP and 3-ketoacyl coenzyme A by AfsA.

Citation: Walsh C, Wencewicz T. 2016. Antibiotic Biosynthesis: Principles, p 276-287. In Antibiotics: Challenges, Mechanisms, Opportunities. ASM Press, Washington, DC. doi: 10.1128/9781555819316.ch14
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Image of Figure 14.9
Figure 14.9

Three different structural platforms for quorum sensors: butyrolactones in different streptomycetes, acylhomoserine lactones in Gram-negative organisms, and peptidylthiolactones in strains of staphylococci. Different molecular scaffolds enable specific instructions in a sea of complex molecules.

Citation: Walsh C, Wencewicz T. 2016. Antibiotic Biosynthesis: Principles, p 276-287. In Antibiotics: Challenges, Mechanisms, Opportunities. ASM Press, Washington, DC. doi: 10.1128/9781555819316.ch14
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Image of Figure 14.10
Figure 14.10

Formation of the 3-ketoacylhomoserine lactone quorum sensors from SAM and the corresponding acyl--ACPs.

Citation: Walsh C, Wencewicz T. 2016. Antibiotic Biosynthesis: Principles, p 276-287. In Antibiotics: Challenges, Mechanisms, Opportunities. ASM Press, Washington, DC. doi: 10.1128/9781555819316.ch14
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