IUPAC/Chemical Name
4-Oxazolecarboxamide, N,N-bis(3-((2,3-dihydroxybenzoyl)amino)propyl)-2-(2,3-dihydroxyphenyl)-4,5-dihydro-5-methyl-, (4S-trans)-
InChi Key
LHJFXHHBUCCXIF-OSPHWJPCSA-N
InChi Code
InChI=1S/C31H34N4O10/c1-17-24(34-30(45-17)20-9-4-12-23(38)27(20)41)31(44)35(15-5-13-32-28(42)18-7-2-10-21(36)25(18)39)16-6-14-33-29(43)19-8-3-11-22(37)26(19)40/h2-4,7-12,17,24,36-41H,5-6,13-16H2,1H3,(H,32,42)(H,33,43)/t17-,24+/m1/s1
SMILES Code
O=C([C@H]1N=C(C2=CC=CC(O)=C2O)O[C@@H]1C)N(CCCNC(C3=CC=CC(O)=C3O)=O)CCCNC(C4=CC=CC(O)=C4O)=O
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
Preparing Stock Solutions
The following data is based on the
product
molecular weight
622.63
Batch specific molecular weights may vary
from batch to batch
due to the degree of hydration, which will
affect the solvent
volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass |
1 mg |
5 mg |
10 mg |
| 1 mM |
1.15 mL |
5.76 mL |
11.51 mL |
| 5 mM |
0.23 mL |
1.15 mL |
2.3 mL |
| 10 mM |
0.12 mL |
0.58 mL |
1.15 mL |
| 50 mM |
0.02 mL |
0.12 mL |
0.23 mL |
1: Sakakura A, Umemura S, Ishihara K. Convergent total syntheses of fluvibactin and vibriobactin using molybdenum(VI) oxide-catalyzed dehydrative cyclization as a key step. Chem Commun (Camb). 2008 Aug 14;(30):3561-3. doi: 10.1039/b805880f. Epub 2008 Jun 6. PMID: 18654713.
2: Wyckoff EE, Allred BE, Raymond KN, Payne SM. Catechol Siderophore Transport by Vibrio cholerae. J Bacteriol. 2015 Sep;197(17):2840-9. doi: 10.1128/JB.00417-15. Epub 2015 Jun 22. PMID: 26100039; PMCID: PMC4524036.
3: 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. PMID: 23755875; PMCID: PMC3783644.
4: Giubergia S, Phippen C, Gotfredsen CH, Nielsen KF, Gram L. Influence of Niche-Specific Nutrients on Secondary Metabolism in Vibrionaceae. Appl Environ Microbiol. 2016 Jun 13;82(13):4035-4044. doi: 10.1128/AEM.00730-16. PMID: 27129958; PMCID: PMC4907173.
5: Yamamoto S, Okujo N, Fujita Y, Saito M, Yoshida T, Shinoda S. Structures of two polyamine-containing catecholate siderophores from Vibrio fluvialis. J Biochem. 1993 May;113(5):538-44. doi: 10.1093/oxfordjournals.jbchem.a124079. PMID: 8340347.
6: Bergeron RJ, Xin MG, Weimar WR, Smith RE, Wiegand J. Significance of asymmetric sites in choosing siderophores as deferration agents. J Med Chem. 2001 Jul 19;44(15):2469-78. doi: 10.1021/jm010019s. PMID: 11448229.
