Nucleotide sequence of Escherichia coli isochorismate synthetase gene entC and evolutionary relationship of isochorismate synthetase and other chorismate-utilizing enzymes

Ozenberger, Bradley A.; Brickman, Timothy J.; McIntosh, Mark A.

doi:10.1128/jb.171.2.775-783.1989

Cited by 118 publications

(84 citation statements)

References 33 publications

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“…Walsh and coworkers (39,40), Earhart and coworkers (41,42), and McIntosh and coworkers (43,44) have shown that enterobactin is synthesized from a fork in the aromatic amino acid pathway in a two-step process (40,41,45). Chorismic acid, an aromatic amino acid precursor, is converted into isochorismate, then into 2,3-dihydro-2,3-dihydroxybenzoate, and finally into 2,3-dihydroxybenzoic acid (DHB).…”

Section: Biosynthesis Of Enterobactinmentioning

confidence: 99%

Enterobactin: An archetype for microbial iron transport

Raymond

Dertz

Kim

2003

Proc. Natl. Acad. Sci. U.S.A.

792

692

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Bacteria have aggressive acquisition processes for iron, an essential nutrient. Siderophores are small iron chelators that facilitate cellular iron transport. The siderophore enterobactin is a triscatechol derivative of a cyclic triserine lactone. Studies of the chemistry, regulation, synthesis, recognition, and transport of enterobactin make it perhaps the best understood of the siderophore-mediated iron uptake systems, displaying a lot of function packed into this small molecule. However, recent surprises include the isolation of corynebactin, a closely related trithreonine triscatechol derivative lactone first found in Gram-positive bacteria, and the crystal structure of a ferric enterobactin complex of a protein identified as an antibacterial component of the human innate immune system.

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Section: Biosynthesis Of Enterobactinmentioning

confidence: 99%

Enterobactin: An archetype for microbial iron transport

Raymond

Dertz

Kim

2003

Proc. Natl. Acad. Sci. U.S.A.

792

692

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“…These include pheA (chorismate mutase-prephenate dehydratase), tyrA (chorismate mutase-prephenate dehydrogenase) (10), entC (isochorismate synthase) (23), pabA and pabB (4-amino-4-deoxychorismate synthase) (6,12), pabC (4-amino-4-deoxychorismate lyase) (7), and trpE and trpD (anthranilate synthase-5-phosphoribosyl-1-pyrophosphate phosphoribosyl transferase) (20,22). * Corresponding author.…”

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confidence: 99%

Cloning and sequencing of Escherichia coli ubiC and purification of chorismate lyase

Nichols

Green

1992

J Bacteriol

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In Escherichia coli, chorismate lyase catalyzes the first step in ubiquinone biosynthesis, the conversion of chorismate to 4-hydroxybenzoate. 4-Hydroxybenzoate is converted to 3-octaprenyl-4-hydroxybenzoate by 4-hydroxybenzoate octaprenyltransferase. These two enzymes are encoded by ubiC and ubi4, respectively, and have been reported to map near one another at 92 min on the E. coli chromosome. We have cloned the ubiCA gene cluster and determined the nucleotide sequence of ubiC and a portion of ubi4. The nucleotide sequence abuts with a previously determined sequence that encodes a large portion of ubi4. ubiC was localized by subcloning, and overproducing plasmids were constructed. Overexpression of ubiC allowed the purification of chorismate lyase to homogeneity, and N-terminal sequence analysis of chorismate lyase unambiguously defined the beginning of the ubiC coding region. Although chorismate lyase showed no significant amino acid sequence similarity to 4-amino-4-deoxychorismate lyase (4-amino-4-deoxychorismate -. 4-aminobenzoate), the product of E. coli pabC, chorismate lyase overproduction could complement the growth requirement for 4-aminobenzoate of a pabC mutant strain. Of the several enzymes that convert chorismate to intermediates of E. coli biosynthetic pathways, chorismate lyase is the last to be isolated and characterized.Chorismate is the branch point precursor for the synthesis of many aromatic compounds in Escherichia coli. The seven major end products of chorismate anabolism are phenylalanine, tyrosine, tryptophan, ubiquinone, 4-aminobenzoate, menaquinone, and enterobactin. Chorismate itself undergoes five different conversions that result in those seven products. The tyrosine and phenylalanine pathways diverge following the isomerization of chorismate to prephenate, but two distinct, homologous chorismate mutase activities channel chorismate toward either phenylalanine or tyrosine (10). The menaquinone and enterobactin pathways diverge following the conversion of chorismate to 2-hydroxy-4-deoxychorismate (isochorismate) by isochorismate synthase (28,30). For 4-aminobenzoate synthesis, chorismate is first aminated to form 4-amino-4-deoxychorismate, which then undergoes ,-elimination of the enol-pyruvyl moiety to form 4-aminobenzoate (1,8,21,29). The first step in ubiquinone biosynthesis is the conversion of chorismate to 4-hydroxybenzoate by chorismate lyase (5, 15), in a reaction apparently similar to the second step of 4-aminobenzoate synthesis, catalyzed by 4-amino-4-deoxychorismate lyase. Finally, the first step in tryptophan synthesis is chorismate amination and p-elimination of the enol-pyruvyl group to form anthranilate, or 2-aminobenzoate (2).With the exception of the genes involved in ubiquinone biosynthesis, all of the E. coli genes encoding enzymes that use chorismate or 4-amino-4-deoxychorismate as substrates have been cloned and sequenced. These include pheA (chorismate mutase-prephenate dehydratase), tyrA (chorismate mutase-prephenate dehydrogenase) (10), entC (isochorismate synth...

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“…In E. coli, the region between the fepB and entC genes is approximately 370 bp, which contains the fepB and entC promoters (6,13,31). These (35).…”

Section: Discussionmentioning

confidence: 99%

“…Transcription of the enterobactin genes, which is regulated by the product of the fur gene and intracellular iron, initiates from two sets of tandem promoters situated between the fepA and fes genes (37,38) and between fepB and entC (13,31). It is likely that additional promoters exist.…”

mentioning

confidence: 99%

“…All but a small portion of the sequence (near the fepB gene) was determined for both DNA strands. The previously determined E. coli sequence of this region (6,13,31), shown on the top strand, is compared with the SA101 sequence shown below it. Several interesting genetic features which may have functions in the regulation of both the fepB and entC genes lie in the region between these two genes.…”

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confidence: 99%

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Genetic analysis of the enterobactin gene cluster in Shigella flexneri

Schmitt

Payne

1991

J Bacteriol

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The genes for transport and synthesis of the phenolate siderophore enterobactin are present on the chromosomes of both Ent' and Ent-clinical isolates of Shigellaflexneri. To determine why Ent-S. flexneri isolates fail to express a functional enterobactin system, the structure and expression of enterobactin genes were examined. Several alterations may be responsible for the inability of S. flexneri to express enterobactin. (i) The mRNA levels produced from the eniC and fepB genes were not derepressed in low-iron media. (ii) DNA sequence analysis of the entC-fepB intergenic region revealed an 83-bp noncontiguous deletion in the putative fepB leader sequence. The deleted sequences are in a region which would be capable of forming extensive stem-and-loop structures. (iii) An amber codon in the 5' portion of the eniC gene was also detected. (iv) An IS) element, previously mapped to the Ent-S.flexneri enterobactin gene cluster, was found to lie within a potential transcriptional termination sequence in the entF-fepE intergenic region. (v) A mutation responsible for the inactivation of the entF gene was mapped to the entF coding region by using entF hybrid gene fusions. (vi) A comparison of outer membrane profiles from an E. coli strain harboring the cloned fepA gene from either an

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Nucleotide sequence of Escherichia coli isochorismate synthetase gene entC and evolutionary relationship of isochorismate synthetase and other chorismate-utilizing enzymes

Cited by 118 publications

References 33 publications

Enterobactin: An archetype for microbial iron transport

Enterobactin: An archetype for microbial iron transport

Cloning and sequencing of Escherichia coli ubiC and purification of chorismate lyase

Genetic analysis of the enterobactin gene cluster in Shigella flexneri

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