Vibriobactin

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MedKoo CAT#: 585373

CAS#: 88217-23-6

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


Price and Availability

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Pricing updated 2020-02-28. Prices are subject to change without notice.

Vibriobactin is not in stock, may be available through custom synthesis. For cost-effective reason, minimum 1 gram order is requested. The product will be characterized by NMR, HPLC and MS analysis. Purity (HPLC) is usually >98%. CoA, QC data, MSDS will be provided when product is successfully made. The estimated lead time is 2-3 months. Please send email to sales@medkoo.com to inquire quote.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 585373
Name: Vibriobactin
CAS#: 88217-23-6
Chemical Formula: C35H39N5O11
Exact Mass: 705.2646
Molecular Weight: 705.721
Elemental Analysis: C, 59.57; H, 5.57; N, 9.92; O, 24.94


Synonym: Vibriobactin; Ferric vibriobactin

IUPAC/Chemical Name: (4R,5S)-N-[3-[3-[(2,3-dihydroxybenzoyl)amino]propyl-[(4S,5R)-2-(2,3-dihydroxyphenyl)-5-methyl-4,5-dihydro-1,3-oxazole-4-carbonyl]amino]propyl]-2-(2,3-dihydroxyphenyl)-5-methyl-4,5-dihydro-1,3-oxazole-4-carboxamide

InChi Key: LLMKLMMXMOTPRU-YOAXHERRSA-N

InChi Code: 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

SMILES Code: O=C([C@@H]1N=C(C2=CC=CC(O)=C2O)O[C@H]1C)NCCCN(CCCNC(C3=CC=CC(O)=C3O)=O)C([C@H]4N=C(C5=CC=CC(O)=C5O)O[C@@H]4C)=O


Technical Data

Appearance:
Solid powder

Purity:
>98% (or refer to the Certificate of Analysis)

Shipping Condition:
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition:
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility:
Soluble in DMSO

Shelf Life:
>3 years if stored properly

Drug Formulation:
This drug may be formulated in DMSO

Stock Solution Storage:
0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code:
2934.99.9001


References

1: Wyckoff EE, Stoebner JA, Reed KE, Payne SM. Cloning of a Vibrio cholerae vibriobactin gene cluster: identification of genes required for early steps in siderophore biosynthesis. J Bacteriol. 1997 Nov;179(22):7055-62. PubMed PMID: 9371453; PubMed Central PMCID: PMC179647.

2: Stoebner JA, Butterton JR, Calderwood SB, Payne SM. Identification of the vibriobactin receptor of Vibrio cholerae. J Bacteriol. 1992 May;174(10):3270-4. PubMed PMID: 1315733; PubMed Central PMCID: PMC205995.

3: Li N, Zhang C, Li B, Liu X, Huang Y, Xu S, Gu L. Unique iron coordination in iron-chelating molecule vibriobactin helps Vibrio cholerae evade mammalian siderocalin-mediated immune response. J Biol Chem. 2012 Mar 16;287(12):8912-9. doi: 10.1074/jbc.M111.316034. Epub 2012 Jan 30. PubMed PMID: 22291019; PubMed Central PMCID: PMC3308770.

4: Kunkle DE, Bina XR, Bina JE. The Vibrio cholerae VexGH RND Efflux System Maintains Cellular Homeostasis by Effluxing Vibriobactin. mBio. 2017 May 16;8(3). pii: e00126-17. doi: 10.1128/mBio.00126-17. PubMed PMID: 28512090; PubMed Central PMCID: PMC5433094.

5: Butterton JR, Calderwood SB. Identification, cloning, and sequencing of a gene required for ferric vibriobactin utilization by Vibrio cholerae. J Bacteriol. 1994 Sep;176(18):5631-8. PubMed PMID: 8083157; PubMed Central PMCID: PMC196765.

6: Wotanis CK, Brennan WP 3rd, Angotti AD, Villa EA, Zayner JP, Mozina AN, Rutkovsky AC, Sobe RC, Bond WG, Karatan E. Relative contributions of norspermidine synthesis and signaling pathways to the regulation of Vibrio cholerae biofilm formation. PLoS One. 2017 Oct 18;12(10):e0186291. doi: 10.1371/journal.pone.0186291. eCollection 2017. PubMed PMID: 29045455; PubMed Central PMCID: PMC5646818.

7: Keating TA, Marshall CG, Walsh CT. Reconstitution and characterization of the Vibrio cholerae vibriobactin synthetase from VibB, VibE, VibF, and VibH. Biochemistry. 2000 Dec 19;39(50):15522-30. PubMed PMID: 11112538.

8: Wyckoff EE, Valle AM, Smith SL, Payne SM. A multifunctional ATP-binding cassette transporter system from Vibrio cholerae transports vibriobactin and enterobactin. J Bacteriol. 1999 Dec;181(24):7588-96. PubMed PMID: 10601218; PubMed Central PMCID: PMC94218.

9: Marshall CG, Burkart MD, Keating TA, Walsh CT. Heterocycle formation in vibriobactin biosynthesis: alternative substrate utilization and identification of a condensed intermediate. Biochemistry. 2001 Sep 4;40(35):10655-63. PubMed PMID: 11524010.

10: Allred BE, Correnti C, Clifton MC, Strong RK, Raymond KN. Siderocalin outwits the coordination chemistry of vibriobactin, a siderophore of Vibrio cholerae. ACS Chem Biol. 2013 Sep 20;8(9):1882-7. doi: 10.1021/cb4002552. Epub 2013 Jun 18. PubMed PMID: 23755875; PubMed Central PMCID: PMC3783644.

11: Butterton JR, Choi MH, Watnick PI, Carroll PA, Calderwood SB. Vibrio cholerae VibF is required for vibriobactin synthesis and is a member of the family of nonribosomal peptide synthetases. J Bacteriol. 2000 Mar;182(6):1731-8. PubMed PMID: 10692380; PubMed Central PMCID: PMC94472.

12: Liu X, Wang Z, Zhu D, Wei T, Gu L, Xu S. Crystallization and preliminary X-ray crystallographic studies of VibE, a vibriobactin-specific 2,3-dihydroxybenzoate-AMP ligase from Vibrio cholerae. Acta Crystallogr Sect F Struct Biol Cryst Commun. 2011 Dec 1;67(Pt 12):1563-5. doi: 10.1107/S1744309111039005. Epub 2011 Nov 25. PubMed PMID: 22139167; PubMed Central PMCID: PMC3232140.

13: Henderson DP, Payne SM. Vibrio cholerae iron transport systems: roles of heme and siderophore iron transport in virulence and identification of a gene associated with multiple iron transport systems. Infect Immun. 1994 Nov;62(11):5120-5. PubMed PMID: 7927795; PubMed Central PMCID: PMC303233.

14: Butterton JR, Stoebner JA, Payne SM, Calderwood SB. Cloning, sequencing, and transcriptional regulation of viuA, the gene encoding the ferric vibriobactin receptor of Vibrio cholerae. J Bacteriol. 1992 Jun;174(11):3729-38. PubMed PMID: 1317381; PubMed Central PMCID: PMC206063.

15: Wyckoff EE, Smith SL, Payne SM. VibD and VibH are required for late steps in vibriobactin biosynthesis in Vibrio cholerae. J Bacteriol. 2001 Mar;183(5):1830-4. PubMed PMID: 11160122; PubMed Central PMCID: PMC95076.

16: Bergeron RJ, Bharti N, Singh S, McManis JS, Wiegand J, Green LG. Vibriobactin antibodies: a vaccine strategy. J Med Chem. 2009 Jun 25;52(12):3801-13. doi: 10.1021/jm900119q. PubMed PMID: 19492834; PubMed Central PMCID: PMC2951131.

17: Elias S, Degtyar E, Banin E. FvbA is required for vibriobactin utilization in Pseudomonas aeruginosa. Microbiology. 2011 Jul;157(Pt 7):2172-2180. doi: 10.1099/mic.0.044768-0. Epub 2011 May 5. PubMed PMID: 21546589.

18: Marshall CG, Hillson NJ, Walsh CT. Catalytic mapping of the vibriobactin biosynthetic enzyme VibF. Biochemistry. 2002 Jan 8;41(1):244-50. PubMed PMID: 11772022.

19: Sigel SP, Stoebner JA, Payne SM. Iron-vibriobactin transport system is not required for virulence of Vibrio cholerae. Infect Immun. 1985 Feb;47(2):360-2. PubMed PMID: 3967921; PubMed Central PMCID: PMC263175.

20: Griffiths GL, Sigel SP, Payne SM, Neilands JB. Vibriobactin, a siderophore from Vibrio cholerae. J Biol Chem. 1984 Jan 10;259(1):383-5. PubMed PMID: 6706943.