MetaCyc Protein Class: a 3,4-dihydroxybenzoyl-[AsbD acyl-carrier protein]

Superclasses: a modified protein

AsbD is an aryl-carrier protein that activates protocatechuate prior to its incorporation into petrobactin. The AsbD protein itself needs to be activated by the transfer of a 4'-phosphopantetheine group from coenzyme A to serine 40 of the apo form, resulting in the active holo form, in a manner similar to other acyl- and aryl-carrier proteins.

The AsbC protein catalyzes the adenylation of protocatechuate, followed by the transfer of the adenylated intermediate to the holo-asbD protein, resulting in a 3,4-dihydroxybenzoyl-[AsbD acyl-carrier protein] [Pfleger07].

Once activated, the protocatechuate moiety can be transferred by AsbE from a 3,4-dihydroxybenzoyl-[AsbD acyl-carrier protein] 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 3,4-dihydroxybenzoyl-[AsbD acyl-carrier protein] compound structure

SMILES: CC(C)(COP(=O)([O-])OCC(N[an apo-AsbD acyl-carrier protein])C(=O)[an apo-AsbD acyl-carrier protein])C(O)C(=O)NCCC(=O)NCCSC(=O)C1(C=CC(O)=C(O)C=1)

Reactions known to consume the compound:

petrobactin biosynthesis :
a 3,4-dihydroxybenzoyl-[AsbD acyl-carrier protein] + N-citryl-spermidine → N1-(3,4-dihydroxybenzoyl)-N8-citryl-spermidine + a holo-[AsbD acyl-carrier protein] + H+
N1-(3,4-dihydroxybenzoyl)-N8,N'8-citryl-bis(spermidine) + a 3,4-dihydroxybenzoyl-[AsbD acyl-carrier protein] → petrobactin + a holo-[AsbD acyl-carrier protein] + H+
N8,N'8-citryl-bis(spermidine) + a 3,4-dihydroxybenzoyl-[AsbD acyl-carrier protein]N1-(3,4-dihydroxybenzoyl)-N8,N'8-citryl-bis(spermidine) + a holo-[AsbD acyl-carrier protein] + H+

Reactions known to produce the compound:

petrobactin biosynthesis :
3,4-dihydroxybenzoate-adenylate + a holo-[AsbD acyl-carrier protein] → a 3,4-dihydroxybenzoyl-[AsbD acyl-carrier protein] + AMP + H+


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
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