MetaCyc Enzyme: 3,4-dihydroxybenzoate-AMP ligase

Gene: asbC Accession Number: G-11393 (MetaCyc)

Species: Bacillus anthracis

asbC encodes an enzyme that catalyzes two functions, both part of the activation of protocatechuate prior to its incorporation into the skeleton of petrobactin.

The first reaction is the adenylation of protocatechuate, resulting in formation of the intermediate 3,4-dihydroxybenzoate-adenylate. In a second reaction the enzyme catalyzes the transfer of the adenylated intermediate to a holo-[AsbD acyl-carrier protein], resulting in a 3,4-dihydroxybenzoyl-[AsbD acyl-carrier protein] [Pfleger07].

Once activated, the protocatechuate moiety can be transferred by the asbE-encoded petrobactin synthase to different receipient molecules, including N-citryl-spermidine, N8,N'8-citryl-bis(spermidine) and N1-(3,4-dihydroxybenzoyl)-N8,N'8-citryl-bis(spermidine) [OvesCostales08].

A deletion mutant of Bacillus anthracis lacking the asbC gene has been constructed, and was not able to grow under iron-limiting conditions [Lee07]. The gene was subsequently cloned and expressed as a His6-fusion protein in Escherichia coli, and the recombinant protein was purified and characterized [Pfleger07].

Molecular Weight of Polypeptide: 46.51 kD (from nucleotide sequence), 47.0 kD (experimental) [Pfleger07 ]

Unification Links: Protein Model Portal:Q81RQ7 , String:198094.BA_1983 , UniProt:Q81RQ7

Relationship Links: InterPro:IN-FAMILY:IPR000873 , InterPro:IN-FAMILY:IPR020845 , InterPro:IN-FAMILY:IPR025110 , Pfam:IN-FAMILY:PF00501 , Pfam:IN-FAMILY:PF13193 , Prosite:IN-FAMILY:PS00455

Gene-Reaction Schematic: ?

Gene-Reaction Schematic

Created 29-Jun-2009 by Caspi R , SRI International

Enzymatic reaction of: 3,4-dihydroxybenzoate-protein ligase (3,4-dihydroxybenzoate-AMP ligase)

3,4-dihydroxybenzoate-adenylate + a holo-[AsbD acyl-carrier protein] <=> a 3,4-dihydroxybenzoyl-[AsbD acyl-carrier protein] + AMP + H+

The reaction direction shown, that is, A + B ↔ C + D versus C + D ↔ A + B, is in accordance with the direction in which it was curated.

The reaction is favored in the direction shown.

In Pathways: petrobactin biosynthesis

Enzymatic reaction of: ATP:protocatechuate adenylyltransferase (3,4-dihydroxybenzoate-AMP ligase)

protocatechuate + ATP + H+ <=> 3,4-dihydroxybenzoate-adenylate + diphosphate

The reaction direction shown, that is, A + B ↔ C + D versus C + D ↔ A + B, is in accordance with the direction in which it was curated.

The reaction is favored in the direction shown.

Alternative Substrates for protocatechuate: 4-hydroxybenzoate [Pfleger07 ] , 3-hydroxybenzoate [Pfleger07 ] , 3,5-dihydroxybenzoate [Pfleger07 ] , 3-amino-5-hydroxybenzoate [Pfleger07 ] , 3-chloro-4-hydroxybenzoate [Pfleger07 ] , 4-fluoro-3-hydroxybenzoate [Pfleger07 ]

In Pathways: petrobactin biosynthesis

Kinetic Parameters:

Km (μM)


Lee07: Lee JY, Janes BK, Passalacqua KD, Pfleger BF, Bergman NH, Liu H, Hakansson K, Somu RV, Aldrich CC, Cendrowski S, Hanna PC, Sherman DH (2007). "Biosynthetic analysis of the petrobactin siderophore pathway from Bacillus anthracis." J Bacteriol 189(5);1698-710. PMID: 17189355

OvesCostales08: Oves-Costales D, Kadi N, Fogg MJ, Song L, Wilson KS, Challis GL (2008). "Petrobactin biosynthesis: AsbB catalyzes condensation of spermidine with N8-citryl-spermidine and its N1-(3,4-dihydroxybenzoyl) derivative." Chem Commun (Camb) (34);4034-6. PMID: 18758617

Pfleger07: Pfleger BF, Lee JY, Somu RV, Aldrich CC, Hanna PC, Sherman DH (2007). "Characterization and analysis of early enzymes for petrobactin biosynthesis in Bacillus anthracis." Biochemistry 46(13);4147-57. PMID: 17346033

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Please cite the following article in publications resulting from the use of MetaCyc: Caspi et al, Nucleic Acids Research 42:D459-D471 2014
Page generated by SRI International Pathway Tools version 19.0 on Sat Oct 10, 2015, BIOCYC14A.