Synthetic studies of thiazoline and thiazolidine-containing natural products. Part 3: Total synthesis and absolute configuration of the siderophore yersiniabactin

Ino, Akira; Murabayashi, Akira

doi:10.1016/s0040-4020(01)00012-6

Cited by 45 publications

(44 citation statements)

References 15 publications

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“…Thiazoline rings with a stereochemistry derived from D-cysteine are also present in the pyochelin-related siderophores yersiniabactin and micacocidin (12,63), and it will be interesting to see if nature has evolved stereoisomers of these compounds as well.…”

Section: Discussionmentioning

confidence: 99%

“…10,11). The presence of iron(III) and zinc(II) were shown to induce a shift from pyochelin II to pyochelin I by converting the S configuration to the R configuration at the chiral center C2Љ (12,13). Similar metal-induced shifts may occur in the other diastereoisomer pairs (Fig.…”

mentioning

confidence: 81%

“…Naturally occurring isomers are pyochelin, isolated from P. aeruginosa PAO1 (10, 11) and enantio-pyochelin, made by P. fluorescens strains Pf-5 and CHA0 (this work). Note that the metalinduced shift (M nϩ ) at C2Љ has only been shown for pyochelin (12,13).…”

mentioning

confidence: 99%

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Pseudomonas fluorescens CHA0 Produces Enantio-pyochelin, the Optical Antipode of the Pseudomonas aeruginosa Siderophore Pyochelin

Youard

Mislin

Majcherczyk

et al. 2007

Journal of Biological Chemistry

106

123

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The siderophore pyochelin is made by a thiotemplate mechanism from salicylate and two molecules of cysteine. In Pseudomonas aeruginosa, the first cysteine residue is converted to its D-isoform during thiazoline ring formation whereas the second cysteine remains in its L-configuration, thus determining the stereochemistry of the two interconvertible pyochelin diastereoisomers as 4R,2؆R,4؆R (pyochelin I) and 4R,2؆S,4؆R (pyochelin II). Pseudomonas fluorescens CHA0 was found to make a different stereoisomeric mixture, which promoted growth under iron limitation in strain CHA0 and induced the expression of its biosynthetic genes, but was not recognized as a siderophore and signaling molecule by P. aeruginosa. Reciprocally, pyochelin promoted growth and induced pyochelin gene expression in P. aeruginosa, but was not functional in P. fluorescens. The structure of the CHA0 siderophore was determined by mass spectrometry, thin-layer chromatography, NMR, polarimetry, and chiral HPLC as enantio-pyochelin, the optical antipode of the P. aeruginosa siderophore pyochelin. Enantio-pyochelin was chemically synthesized and confirmed to be active in CHA0. Its potential biosynthetic pathway in CHA0 is discussed.

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Section: Discussionmentioning

confidence: 99%

mentioning

confidence: 81%

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Pseudomonas fluorescens CHA0 Produces Enantio-pyochelin, the Optical Antipode of the Pseudomonas aeruginosa Siderophore Pyochelin

Youard

Mislin

Majcherczyk

et al. 2007

Journal of Biological Chemistry

106

123

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“…Potato tuber tissue was heavily necrotized by both wild-type and DSCAB1471 strains 7 days post-inoculation, suggesting that pyochelin (2007). The occurrence of two isomers for both pyochelin and ent-pyochelin is a result of a metal-induced epimerisation at C-299 (Ino & Murabayashi, 2001;Schlegel et al, 2004).…”

Section: Scab1371 Activates Transcription Of the Pbgcmentioning

confidence: 99%

The plant pathogen Streptomyces scabies 87-22 has a functional pyochelin biosynthetic pathway that is regulated by TetR- and AfsR-family proteins

et al. 2011

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The plant pathogen Streptomyces scabies 87-22 has a functional pyochelin biosynthetic pathway that is regulated by TetR-and AfsR-family proteins Siderophores are high-affinity iron-chelating compounds produced by bacteria for iron uptake that can act as important virulence determinants for both plant and animal pathogens. Genome sequencing of the plant pathogen Streptomyces scabies 87-22 revealed the presence of a putative pyochelin biosynthetic gene cluster (PBGC). Liquid chromatography (LC)-MS analyses of culture supernatants of S. scabies mutants, in which expression of the cluster is upregulated and which lack a key biosynthetic gene from the cluster, indicated that pyochelin is a product of the PBGC. LC-MS comparisons with authentic standards on a homochiral stationary phase confirmed that pyochelin and not enantio-pyochelin (ent-pyochelin) is produced by S. scabies. Transcription of the S. scabies PBGC occurs via~19 kb and~3 kb operons and transcription of the~19 kb operon is regulated by TetR-and AfsR-family proteins encoded by the cluster. This is the first report, to our knowledge, of pyochelin production by a Gram-positive bacterium; interestingly regulation of pyochelin production is distinct from characterized PBGCs in Gram-negative bacteria. Though pyochelin-mediated iron acquisition by Pseudomonas aeruginosa is important for virulence, in planta bioassays failed to demonstrate that pyochelin production by S. scabies is required for development of disease symptoms on excised potato tuber tissue or radish seedlings. INTRODUCTIONThe genus Streptomyces is comprised of hundreds of species, most of which are soil-dwelling and saprophytic. The ability of these filamentous actinobacteria to produce biologically active secondary metabolites is well known; streptomycetes produce nearly two-thirds of the world's naturally occurring antibiotics (Bentley et al., 2002). Since soil is poor in nutrients but rich in microbial competitors, most secondary metabolites are thought to serve as antimicrobial agents. However, secondary metabolites have other roles, one of which is iron acquisition. Iron is relatively unavailable to soil bacteria due to the low solubility of the Fe 3+ ion under aerobic conditions at neutral pH. The most common way that bacteria cope with low bioavailability of iron is the production of ironchelating compounds called siderophores (Guerinot, 1994). Production of siderophores by saprophytic Streptomyces species has been known since the 1960s; desferrioxamine siderophores are produced by multiple Streptomyces species ( Barona-Gó mez et al., 2004Bickel et al., 1960;Imbert et al., 1995;Schupp et al., 1988). Recently, streptomycetes have been found to produce siderophores other than desferrioxamines. Streptomyces sp. Tü 6125 produces enterobactin, a catecholate-type siderophore typically produced by members of the family Enterobacteriaceae (Fiedler et al., 2001). Streptomyces sp. ATCC 700974 and Streptomyces griseus produce griseobactin, a siderophore containing catechol, threonine and arginine t...

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“…The yersiniabactin molecule has an extremely high affinity for ferric iron (K D = 4 × 10 -36 ; Gehring et al, 1998a; Perry et al, 1999). The biochemical structures and functions of different components of the machinery involved in the nonribosomal biosynthesis of yersiniabactin are currently under investigation (Suo et al, 1999;Suo et al, 2000;Suo et al, 2001;Keating et al, 2000a;Keating et al, 2000b;Ino and Murabayashi, 2001).…”

Section: High-pathogenicity Island (Elisabeth Carniel)mentioning

confidence: 99%

Y. enterocolitica and Y. pseudotuberculosis

Carniel¹,

Autenrieth²,

Cornelis³

et al. 2006

The Prokaryotes

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Synthetic studies of thiazoline and thiazolidine-containing natural products. Part 3: Total synthesis and absolute configuration of the siderophore yersiniabactin

Cited by 45 publications

References 15 publications

Pseudomonas fluorescens CHA0 Produces Enantio-pyochelin, the Optical Antipode of the Pseudomonas aeruginosa Siderophore Pyochelin

Pseudomonas fluorescens CHA0 Produces Enantio-pyochelin, the Optical Antipode of the Pseudomonas aeruginosa Siderophore Pyochelin

The plant pathogen Streptomyces scabies 87-22 has a functional pyochelin biosynthetic pathway that is regulated by TetR- and AfsR-family proteins

Y. enterocolitica and Y. pseudotuberculosis

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