Biosynthesis of fluorothreonine and fluoroacetic acid by the thienamycin producer, Streptomyces cattleya.

Sanada, M; Miyano, Tetsuji; Iwadare, Shuichi; Williamson, Joanne M.; Arison, Byron H.; Smith, Jack L.; Douglas, Alan W.; Liesch, Jerrold M.; Inamine, Edward

doi:10.7164/antibiotics.39.259

Cited by 158 publications

(105 citation statements)

References 8 publications

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“…Sanada et al (15) reported that Streptomyces cattleya NRRL 8057, a thienamycin producer, produces fluoroacetate and 4-fluorothreonine from the inorganic fluoride anion. However, it has not been shown whether fluoroacetate is first produced as a fluorinated metabolite or whether it is derived through 4-fluorothreonine.…”

mentioning

confidence: 99%

Synthesis of fluoroacetate from fluoride, glycerol, and beta-hydroxypyruvate by Streptomyces cattleya

et al. 1995

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mentioning

confidence: 99%

Synthesis of fluoroacetate from fluoride, glycerol, and beta-hydroxypyruvate by Streptomyces cattleya

et al. 1995

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“…In 1986, a Streptomyces cattleya strain was reported to produce fluoroacetate and fluorothreonine (Sanada et al 1986). …”

Section: Importance Of Fluorine In Pharmaceutical Compoundsmentioning

confidence: 99%

Metabolism of fluoroorganic compounds in microorganisms: impacts for the environment and the production of fine chemicals

Murphy

Clark

Amadio

2009

Appl Microbiol Biotechnol

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Publication information Applied Microbiology and Biotechnology, 84 (4): 617-629Publisher Springer Item record/more information http://hdl.handle.net/10197/5314 Publisher's statementThe final publication is available at www.springerlink.com can lead to the generation of toxic compounds that are of environmental concern, yet similar biotransformations can yield difficult-to-synthesise products and intermediates, in particular derivatives of biologically active secondary metabolites. In this paper we review the historical and recent developments of organofluorine biotransformation in microorganisms, and highlight the possibility of using microbes as models of fluorinated drug metabolism in mammals.3

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“…Most other natural amino acid toxins require more enzymatic steps for their formation, e.g., the well-known arginine analogue canavanine, which is produced by the jack bean (Canavalia ensiformis) (23). Even though natural products from microorganisms make use of rare amino acids as constituents of non-ribosomally produced peptides, only a few free nonproteinogenic amino acids, such as MeArg, are known to come from microorganisms (25). Free rare amino acids appear to be more common among plants and often serve as defense compounds (12).…”

Section: Vol 76 2010mentioning

confidence: 99%

Identification of the Biosynthetic Gene Cluster for 3-Methylarginine, a Toxin Produced by Pseudomonas syringae pv. syringae 22d/93

Hofmann¹,

Wensing

Ullrich

et al. 2010

Appl Environ Microbiol

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The epiphyte Pseudomonas syringae pv. syringae 22d/93 (Pss22d) produces the rare amino acid 3-methylarginine (MeArg), which is highly active against the closely related soybean pathogen Pseudomonas syringae pv. glycinea. Since these pathogens compete for the same habitat, Pss22d is a promising candidate for biocontrol of P. syringae pv. glycinea. The MeArg biosynthesis gene cluster codes for the S-adenosylmethionine (SAM)-dependent methyltransferase MrsA, the putative aminotransferase MrsB, and the amino acid exporter MrsC. Transfer of the whole gene cluster into Escherichia coli resulted in heterologous production of MeArg. The methyltransferase MrsA was overexpressed in E. coli as a His-tagged protein and functionally characterized (K m , 7 mM; k cat , 85 min ؊1 ). The highly selective methyltransferase MrsA transfers the methyl group from SAM into 5-guanidino-2-oxo-pentanoic acid to yield 5-guanidino-3-methyl-2-oxo-pentanoic acid, which then only needs to be transaminated to result in the antibiotic MeArg.Microbial plant pathogens cause severe losses in agriculture each year (1). For example, the plant pathogen Pseudomonas syringae pv. glycinea is responsible for bacterial blight of soybean, a leaf spot disease of great economic impact. Besides chemical treatment, biocontrol agents that antagonize microbial plant pathogens are gaining increasing importance in fighting plant diseases (6,11,27). In a screening for possible biocontrol strains, an epiphytic bacterium showing a strong and selective activity against the pathogen P. syringae pv. glycinea was isolated from soybean leaves (29). The strain was characterized as Pseudomonas syringae pv. syringae 22d/93 (Pss22d). The antagonism of Pss22d against P. syringae pv. glycinea has been demonstrated successfully in vitro and in planta under greenhouse and field conditions (19,29). In order to identify the molecular basis of the antagonism of Pss22d against P. syringae pv. glycinea, we focused on its secondary metabolites. Besides the well-known lipodepsipeptides syringomycin and syringopeptin (3), Pss22d produces the rare amino acid 3-methylarginine (MeArg) (5). As little as 20 nmol of MeArg strongly and selectively inhibits P. syringae pv. glycinea but no other pseudomonads in vitro (29). Since the inhibition can be compensated for by L-arginine supplementation but not by any other essential amino acid, it is likely that the toxin acts as an inhibitor of the arginine biosynthesis pathway or an argininedependent pathway, such as nitric oxide formation (13,16). Feeding experiments and Tn5 transposon mutagenesis suggested that MeArg is produced by an S-adenosyl methionine (SAM)-dependent methyltransferase (5) converting the enol of 5-guanidino-2-oxo-pentanoic acid to 5-guanidino-3-methyl-2-oxo-pentanoic acid. An analogous reaction is known to occur with the methyltransferases GlmT, DptI, and LptI, which form 3-methylglutamate from ␣-ketoglutarate (18). On the way to MeArg, only a transaminase catalyzing the formation of MeArg from 5-guanidino-3-methyl-2-oxo-pentano...

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Biosynthesis of fluorothreonine and fluoroacetic acid by the thienamycin producer, Streptomyces cattleya.

Cited by 158 publications

References 8 publications

Synthesis of fluoroacetate from fluoride, glycerol, and beta-hydroxypyruvate by Streptomyces cattleya

Synthesis of fluoroacetate from fluoride, glycerol, and beta-hydroxypyruvate by Streptomyces cattleya

Metabolism of fluoroorganic compounds in microorganisms: impacts for the environment and the production of fine chemicals

Identification of the Biosynthetic Gene Cluster for 3-Methylarginine, a Toxin Produced by Pseudomonas syringae pv. syringae 22d/93

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