The Biosynthesis of Phenazines
The phenazines are nitrogen-containing colored aromatic secondary metabolites that many bacterial species produce and excrete into the environment, sometimes in such large quantities that they are visible to the naked eye. Phenazines act as broad-specific
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The Biosynthesis of Phenazines Wulf Blankenfeldt
Abstract The phenazines are nitrogen-containing colored aromatic secondary metabolites that many bacterial species produce and excrete into the environment, sometimes in such large quantities that they are visible to the naked eye. Phenazines act as broad-specificity antibiotics and as virulence as well as survival factors in infectious disease, which is in general a consequence of their redox activity. This chapter gives a historical perspective of research that led to our current understanding of phenazine biosynthesis, starting with the isolation of the first phenazine derivative pyocyanin in 1859. The focus is on recent biochemical and structural studies of the enzymes PhzE, PhzD, PhzF, PhzB, and PhzG, which convert chorismic acid via 2-amino-2-desoxyisochorismic acid (ADIC), trans-2,3dihydro-3-hydroxyanthranilic acid (DHHA), 6-amino-5-oxocyclohex-2-ene-1carboxylic acid (AOCHC), hexahydro-phenazine-1,6-dicarboxylate (HHPDC), and tetrahydro-phenazine-1-carboxylate (THPCA) to phenazine-1,6-dicarboxylic acid (PDC) and phenazine-1-carboxylic acid (PCA). PDC and PCA then act as ‘‘core’’ phenazines that strain-specific enzymes convert to the over 150 phenazine derivatives that have been isolated from natural sources until today.
1.1 The Discovery of Phenazines and Phenazine-Producing Bacteria The unexpected occurrence of light or color in or on apparently inanimate objects has fascinated mankind since its early days and is the basis for fairy tales and even religious beliefs and traditions. For example, the appearance of a red liquid on bread mistakenly interpreted as blood was foreseen as a good omen that led W. Blankenfeldt (&) Lehrstuhl für Biochemie and Bayreuther Zentrum für Molekulare Biowissenschaften, Universität Bayreuth, Universitätsstraße 30, 95447 Bayreuth, Germany e-mail: [email protected]; [email protected]
S. Chincholkar and L. Thomashow (eds.), Microbial Phenazines, DOI: 10.1007/978-3-642-40573-0_1, Springer-Verlag Berlin Heidelberg 2013
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Alexander the Great to attack and conquer Tyros in 332 B.C. The same phenomenon provided the transubstantiation ‘‘miracle’’ that convinced the priest Peter of Prague of the trueness of the conversion of bread into the body of Christ while celebrating Eucharist in Bolsena (Italy) in 1263, which gave rise to the still celebrated ‘‘Feast of Corpus Christi’’ by the Catholic Church. ‘‘Milky seas’’ accounted for tales among seafarers for hundreds of years and are also featured in Jules Verne’s ‘‘Twenty Thousand Leagues Under the Sea’’ from 1870. References to ‘‘blue milk’’ originating in the sixteenth century appear in Jakob and Wilhelm Grimm’s German Dictionary from 1854 and also in books on veterinary medicine from the early days of book printing. All of these phenomena result from the presence of microorganisms: the blue color in dairy products is associated with Pseudomonas strains (Martin et al. 2011; Seiler 2006), although ancient texts may also mean skimmed
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