Ornibactin

Chemical compound From Wikipedia, the free encyclopedia

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]

CAS Number
PubChem CID
FormulaC28H52N8O13
Molar mass708.767 g·mol−1
Quick facts Identifiers, CAS Number ...
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
Close

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.

Biosynthesis of Ornibactin
Biosynthesis of Ornibactin

References

Related Articles

Wikiwand AI