Vibriobactin

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Vibriobactin
Vibriobactin.svg
Names
Preferred IUPAC name
(4S,5R)-N-[3-(2,3-Dihydroxybenzamido)propyl]-2-(2,3-dihydroxyphenyl)-5-methyl-N-{3-[(4R,5S)-5-methyl-2-(2,3-dihydroxyphenyl)-4,5-dihydro-1,3-oxazole-4-carboxamido]propyl}-4,5-dihydro-1,3-oxazole-4-carboxamide
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
KEGG
  • InChI=1S/C35H39N5O11/c1-18-26(38-33(50-18)21-9-4-12-24(42)29(21)45)32(48)37-15-7-17-40(16-6-14-36-31(47)20-8-3-11-23(41)28(20)44)35(49)27-19(2)51-34(39-27)22-10-5-13-25(43)30(22)46/h3-5,8-13,18-19,26-27,41-46H,6-7,14-17H2,1-2H3,(H,36,47)(H,37,48)/t18-,19+,26+,27-/m0/s1
    Key: LLMKLMMXMOTPRU-YOAXHERRSA-N
  • Ferric:: InChI=1S/C35H39N5O11.Fe/c1-18-26(38-33(50-18)21-9-4-12-24(42)29(21)45)32(48)37-15-7-17-40(16-6-14-36-31(47)20-8-3-11-23(41)28(20)44)35(49)27-19(2)51-34(39-27)22-10-5-13-25(43)30(22)46;/h3-5,8-13,18-19,26-27,41-46H,6-7,14-17H2,1-2H3,(H,36,47)(H,37,48);/q;+3/p-6/t18-,19+,26+,27-;/m0./s1
    Key: XCZXQZJLNMPXIV-VBIAIPROSA-H
  • C[C@H]1[C@@H](N=C(O1)C2=C(C(=CC=C2)O)O)C(=O)NCCCN(CCCNC(=O)C3=C(C(=CC=C3)O)O)C(=O)[C@@H]4[C@H](OC(=N4)C5=C(C(=CC=C5)O)O)C
  • Ferric:: [H][C@@]12N=C(O[C@H]1C)c1cccc3[O-][Fe+3]456([O-]c7cccc(C(=O)NCCCN(CCCNC2=O)C(=O)[C@@]2([H])N=C(O[C@@H]2C)c2cccc([O-]4)c2[O-]5)c7[O-]6)[O-]c13
Properties
C35H39N5O11
Molar mass 705.721 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Vibriobactin is a catechol siderophore that helps the microbial system to acquire iron. It was first isolated from Vibrio cholerae.[1]

Structure and biosynthesis[edit]

The components of vibriobactin are three 2,3-dihydroxybenzoic acid (DHB), two threonine (Thr), and one norspermidine (NSPD). DHB is synthesized from chorismic acid by a series of enzymes: VibA, VibB, and VibC. DHB is linked to NSPD by VibE, VibB and VibH in order and forms DHB-NSPD.[2] On the other hand, DHB performs condensation and cyclization with Thr by VibE, VibB, and VibF to form the heterocyclic molecule linked on VibF: DHB-Thr-VibF. DHB-NSPD and DHB-Thr-VibF are then put together by VibF to form vibriobactin.[3]

Vibriobactin biosynthesis.png

References[edit]

  1. ^ Griffiths, Gary L.; Sigel, Suzanne P.; Payne, Shelley M.; Neilands, J. B. (1984). "Vibriobactin, a Siderophore from Vibrio cholerae". The Journal of Biological Chemistry. 259 (1): 383–385. doi:10.1016/S0021-9258(17)43671-4. PMID 6706943.
  2. ^ Keating, Thomas A.; Marshall, C. Gary; Walsh, Christopher T. (2000). "Vibriobactin Biosynthesis in Vibrio cholerae: VibH Is an Amide Synthase Homologous to Nonribosomal Peptide Synthetase Condensation Domains". Biochemistry. 39 (50): 15514. doi:10.1021/bi001651a. PMID 11112537.
  3. ^ Marshall, C. Gary; Burkart, Michael D.; Keating, Thomas A.; Walsh, Christopher T. (2001). "Heterocycle Formation in Vibriobactin Biosynthesis: Alternative Substrate Utilization and Identification of a Condensed Intermediate". Biochemistry. 40 (35): 10656. doi:10.1021/bi010937s. PMID 11524010.