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Enzymatic logic of anthrax stealth siderophore biosynthesis: AsbA catalyzes ATP-Dependent condensation of citric acid and spermidine
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Oves-Costales, Daniel, Kadi, Nadia, Fogg, Mark J., Song, Lijiang, Wilson, Keith S. and Challis, Gregory L. (2007) Enzymatic logic of anthrax stealth siderophore biosynthesis: AsbA catalyzes ATP-Dependent condensation of citric acid and spermidine. Journal of the American Chemical Society, Vol.129 (No.27). pp. 8416-8417. doi:10.1021/ja072391o ISSN 0002-7863.
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Official URL: http://dx.doi.org/10.1021/ja072391o
Abstract
Petrobactin is an iron-chelating siderophore originally isolated from Marinobacter hydrocarbonoclasticus that has been shown to play an important role in growth under iron-deficient conditions and virulence of the deadly bioterrorism agent Bacillus anthracis. It has recently been shown not to bind to siderocalin, leading it to be designated as a "stealth siderophore" that can avoid the mammalian immune system. A unique combination of nonribosomal peptide synthetase (NRPS) and NRPS-independent siderophore (NIS) synthetase enzymes is known to be required for petrobactin biosynthesis in B. anthracis. Here it is shown that AsbA from B. anthracis, the first type A NIS synthetase to be biochemically characterized, catalyzes ATP-dependent regioselective condensation of citric acid with N-8 of spermidine, but not with N-1-(3,4-dihydroxybenzoyl)-spermidine. These results rule out a recently proposed pathway for petrobactin biosynthesis involving AsbA-catalyzed condensation of N-1-(3,4-dihydroxybenzoyl)-spermidine with citric acid and show that acylation of N-1 of spermidine with the 3,4-dihydroxybenzoyl group must occur after acylation of N-8 of spermidine with citrate. They also provide the fundamental knowledge needed to establish a high throughput screen for inhibitors of AsbA that may provide the basis for development of new antibiotics for the treatment of deadly anthrax infections.
| Item Type: | Journal Article | ||||
|---|---|---|---|---|---|
| Subjects: | Q Science > QD Chemistry | ||||
| Divisions: | Faculty of Science, Engineering and Medicine > Science > Chemistry | ||||
| Journal or Publication Title: | Journal of the American Chemical Society | ||||
| Publisher: | American Chemical Society | ||||
| ISSN: | 0002-7863 | ||||
| Official Date: | 11 July 2007 | ||||
| Dates: |
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| Volume: | Vol.129 | ||||
| Number: | No.27 | ||||
| Number of Pages: | 2 | ||||
| Page Range: | pp. 8416-8417 | ||||
| DOI: | 10.1021/ja072391o | ||||
| Status: | Peer Reviewed | ||||
| Publication Status: | Published | ||||
| Access rights to Published version: | Restricted or Subscription Access |
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