Ornibactin

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Ornibactin
Identifiers
  • (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
CAS Number
PubChem CID
Chemical and physical data
FormulaC28H52N8O13
Molar mass708.767 g·mol−1
3D model (JSmol)
  • 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
  • InChI=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
  • Key:ZQCAUNGVEIYRKP-VCYWQZMXSA-N

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[edit]

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.

Biosynthesis of Ornibactin
Biosynthesis of Ornibactin

References[edit]

  1. ^ Braun V, Braun M (April 2002). "Active transport of iron and siderophore antibiotics". Current Opinion in Microbiology. 5 (2): 194–201. doi:10.1016/s1369-5274(02)00298-9. PMID 11934617.
  2. ^ Sokol PA, Darling P, Lewenza S, Corbett CR, Kooi CD (December 2000). "Identification of a siderophore receptor required for ferric ornibactin uptake in Burkholderia cepacia". Infection and Immunity. 68 (12): 6554–60. doi:10.1128/iai.68.12.6554-6560.2000. PMC 97749. PMID 11083764.
  3. ^ Meyer JM, Van VT, Stintzi A, Berge O, Winkelmann G (October 1995). "Ornibactin production and transport properties in strains of Burkholderia vietnamiensis and Burkholderia cepacia (formerly Pseudomonas cepacia)". Biometals. 8 (4): 309–17. doi:10.1007/bf00141604. PMID 7580051. S2CID 21962818.
  4. ^ Coenye T, Vandamme P, Govan JR, LiPuma JJ (October 2001). "Taxonomy and identification of the Burkholderia cepacia complex". Journal of Clinical Microbiology. 39 (10): 3427–36. doi:10.1128/jcm.39.10.3427-3436.2001. PMC 88367. PMID 11574551.
  5. ^ LiPuma JJ (September 1998). "Burkholderia cepacia. Management issues and new insights". Clinics in Chest Medicine. 19 (3): 473–86, vi. doi:10.1016/s0272-5231(05)70094-0. PMID 9759550.
  6. ^ Speert DP (September 2002). "Advances in Burkholderia cepacia complex". Paediatric Respiratory Reviews. 3 (3): 230–5. doi:10.1016/s1526-0542(02)00185-9. PMID 12376059.
  7. ^ Stephan H, Freund S, Beck W, Jung G, Meyer JM, Winkelmann G (1993). "Ornibactins--a new family of siderophores from Pseudomonas". Biometals. 6 (2): 93–100. doi:10.1007/bf00140109. PMID 7689374. S2CID 23706945.
  8. ^ Agnoli K, Lowe CA, Farmer KL, Husnain SI, Thomas MS (May 2006). "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. doi:10.1128/jb.188.10.3631-3644.2006. PMC 1482860. PMID 16672617.


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