Ornibactin Explained

Pubchem:102081710
Cas Number:154071-69-9
C:28
H:52
N:8
O:13
Smiles:CCCC(CC(=O)N(CCC[C@@H](C(=O)N[C@H]([C@H](C(=O)O)O)C(=O)N[C@@H](CO)C(=O)N[C@@H](CCCN(C=O)O)C(=O)NCCCCN)N)O)O
Stdinchi:1S/C28H52N8O13/c1-2-7-17(39)14-21(40)36(49)13-5-8-18(30)24(42)34-22(23(41)28(46)47)27(45)33-20(15-37)26(44)32-19(9-6-12-35(48)16-38)25(43)31-11-4-3-10-29/h16-20,22-23,37,39,41,48-49H,2-15,29-30H2,1H3,(H,31,43)(H,32,44)(H,33,45)(H,34,42)(H,46,47)/t17?,18-,19-,20-,22+,23+/m0/s1
Stdinchikey:ZQCAUNGVEIYRKP-VCYWQZMXSA-N
Iupac Name:(2R,3R)-4-(2S)-1-(2S)-1-(4-aminobutylamino)-5-[formyl(hydroxy)amino]-1-oxopentan-2-yl]amino]-3-hydroxy-1-oxopropan-2-yl]amino]-3-(2S)-2-amino-5-[hydroxy(3-hydroxyhexanoyl)amino]pentanoyl]amino]-2-hydroxy-4-oxobutanoic acid

Ornibactin is a siderophore, or small iron-binding compound secreted by bacteria to transport iron into the cell.[1] Ornibactin is produced by Burkholderia cenocepacia under iron-deficient conditions.[2] [3] B. cenocepacia is known to opportunistically infect humans, specifically ones suffering from cystic fibrosis.[4] [5] [6]

Biosynthesis

Ornibactin consists of an L-ornithine-D-hydroxyaspartate-L-serine-L-ornithine backbone.[7] It is biosynthesized by 2 non-ribosomal peptide synthetases (NRPSs), OrbI and OrbJ, as indicated in the figure below.[8] The domains are as follows: adenylation (A), peptidyl carrier (P), condensation (C), and epimerase (E). The wavy lines in the figure indicate the phosphopantetheine arms to which the amino acid residues are attached via thioester linkages.

Notes and References

  1. Braun V, Braun M . Active transport of iron and siderophore antibiotics . Current Opinion in Microbiology . 5 . 2 . 194–201 . April 2002 . 11934617 . 10.1016/s1369-5274(02)00298-9 .
  2. Sokol PA, Darling P, Lewenza S, Corbett CR, Kooi CD . Identification of a siderophore receptor required for ferric ornibactin uptake in Burkholderia cepacia . Infection and Immunity . 68 . 12 . 6554–60 . December 2000 . 11083764 . 97749 . 10.1128/iai.68.12.6554-6560.2000 .
  3. Meyer JM, Van VT, Stintzi A, Berge O, Winkelmann G . Ornibactin production and transport properties in strains of Burkholderia vietnamiensis and Burkholderia cepacia (formerly Pseudomonas cepacia) . Biometals . 8 . 4 . 309–17 . October 1995 . 7580051 . 10.1007/bf00141604 . 21962818 .
  4. Coenye T, Vandamme P, Govan JR, LiPuma JJ . Taxonomy and identification of the Burkholderia cepacia complex . Journal of Clinical Microbiology . 39 . 10 . 3427–36 . October 2001 . 11574551 . 88367 . 10.1128/jcm.39.10.3427-3436.2001 .
  5. LiPuma JJ . Burkholderia cepacia. Management issues and new insights . Clinics in Chest Medicine . 19 . 3 . 473–86, vi . September 1998 . 9759550 . 10.1016/s0272-5231(05)70094-0 .
  6. Speert DP . Advances in Burkholderia cepacia complex . Paediatric Respiratory Reviews . 3 . 3 . 230–5 . September 2002 . 12376059 . 10.1016/s1526-0542(02)00185-9 .
  7. Stephan H, Freund S, Beck W, Jung G, Meyer JM, Winkelmann G . Ornibactins--a new family of siderophores from Pseudomonas . Biometals . 6 . 2 . 93–100 . 1993 . 7689374 . 10.1007/bf00140109 . 23706945 .
  8. Agnoli K, Lowe CA, Farmer KL, Husnain SI, Thomas MS . The ornibactin biosynthesis and transport genes of Burkholderia cenocepacia are regulated by an extracytoplasmic function sigma factor which is a part of the Fur regulon . Journal of Bacteriology . 188 . 10 . 3631–44 . May 2006 . 16672617 . 1482860 . 10.1128/jb.188.10.3631-3644.2006 .

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