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MedKoo Cat#: 585396 | Name: Vulnibactin

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Vulnibactin, isolated from Vibrio vulnificus, is a catechol-siderophore that is required for iron-assimilation from transferrin.

Chemical Structure

Vulnibactin
Vulnibactin
CAS#156368-88-6

Theoretical Analysis

MedKoo Cat#: 585396

Name: Vulnibactin

CAS#: 156368-88-6

Chemical Formula: C35H39N5O9

Exact Mass: 673.2748

Molecular Weight: 673.72

Elemental Analysis: C, 62.40; H, 5.84; N, 10.40; O, 21.37

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
No Data
Synonym
Vulnibactin
IUPAC/Chemical Name
N-[3-[3-[(2,3-dihydroxybenzoyl)amino]propyl-[2-(2-hydroxyphenyl)-5-methyl-4,5-dihydro-1,3-oxazole-4-carbonyl]amino]propyl]-2-(2-hydroxyphenyl)-5-methyl-4,5-dihydro-1,3-oxazole-4-carboxamide
InChi Key
CYQRDZPBFHTFJZ-UHFFFAOYSA-N
InChi Code
InChI=1S/C35H39N5O9/c1-20-28(38-33(48-20)22-10-3-5-13-25(22)41)32(46)37-17-9-19-40(18-8-16-36-31(45)24-12-7-15-27(43)30(24)44)35(47)29-21(2)49-34(39-29)23-11-4-6-14-26(23)42/h3-7,10-15,20-21,28-29,41-44H,8-9,16-19H2,1-2H3,(H,36,45)(H,37,46)
SMILES Code
O=C(C1N=C(C2=CC=CC=C2O)OC1C)NCCCN(CCCNC(C3=CC=CC(O)=C3O)=O)C(C4N=C(C5=CC=CC=C5O)OC4C)=O
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
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 673.72 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.

Recalculate based on batch purity %
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: Kawano H, Miyamoto K, Yasunobe M, Murata M, Yamahata E, Yamaguchi R, Miyaki Y, Tsuchiya T, Tanabe T, Funahashi T, Tsujibo H. Identification of the heme acquisition system in Vibrio vulnificus M2799. Microb Pathog. 2018 Apr;117:100-108. doi: 10.1016/j.micpath.2018.02.022. Epub 2018 Feb 10. PubMed PMID: 29432914. 2: Kawano H, Miyamoto K, Negoro M, Zushi E, Tsuchiya T, Tanabe T, Funahashi T, Tsujibo H. IutB participates in the ferric-vulnibactin utilization system in Vibrio vulnificus M2799. Biometals. 2017 Apr;30(2):203-216. doi: 10.1007/s10534-017-9994-0. Epub 2017 Feb 1. PubMed PMID: 28150143. 3: Kim CM, Ahn YJ, Kim SJ, Yoon DH, Shin SH. Temperature Change Induces the Expression of vuuA Encoding Vulnibactin Receptor and crp Encoding Cyclic AMP Receptor Protein in Vibrio vulnificus. Curr Microbiol. 2016 Jul;73(1):54-64. doi: 10.1007/s00284-016-1026-8. Epub 2016 Mar 25. PubMed PMID: 27016238. 4: Kawano H, Miyamoto K, Sakaguchi I, Myojin T, Moriwaki M, Tsuchiya T, Tanabe T, Yamamoto S, Tsujibo H. Role of periplasmic binding proteins, FatB and VatD, in the vulnibactin utilization system of Vibrio vulnificus M2799. Microb Pathog. 2013 Dec;65:73-81. doi: 10.1016/j.micpath.2013.10.002. Epub 2013 Oct 14. PubMed PMID: 24135791. 5: Kawano H, Miyamoto K, Yasunobe M, Murata M, Myojin T, Tsuchiya T, Tanabe T, Funahashi T, Sato T, Azuma T, Mino Y, Tsujibo H. The RND protein is involved in the vulnibactin export system in Vibrio vulnificus M2799. Microb Pathog. 2014 Oct;75:59-67. doi: 10.1016/j.micpath.2014.09.001. Epub 2014 Sep 6. PubMed PMID: 25205089. 6: Tan W, Verma V, Jeong K, Kim SY, Jung CH, Lee SE, Rhee JH. Molecular characterization of vulnibactin biosynthesis in Vibrio vulnificus indicates the existence of an alternative siderophore. Front Microbiol. 2014 Jan 24;5:1. doi: 10.3389/fmicb.2014.00001. eCollection 2014. PubMed PMID: 24478763; PubMed Central PMCID: PMC3900857. 7: Kim CM, Park RY, Park JH, Sun HY, Bai YH, Ryu PY, Kim SY, Rhee JH, Shin SH. Vibrio vulnificus vulnibactin, but not metalloprotease VvpE, is essentially required for iron-uptake from human holotransferrin. Biol Pharm Bull. 2006 May;29(5):911-8. PubMed PMID: 16651718. 8: Okujo N, Akiyama T, Miyoshi S, Shinoda S, Yamamoto S. Involvement of vulnibactin and exocellular protease in utilization of transferrin- and lactoferrin-bound iron by Vibrio vulnificus. Microbiol Immunol. 1996;40(8):595-8. PubMed PMID: 8887355. 9: Webster AC, Litwin CM. Cloning and characterization of vuuA, a gene encoding the Vibrio vulnificus ferric vulnibactin receptor. Infect Immun. 2000 Feb;68(2):526-34. PubMed PMID: 10639413; PubMed Central PMCID: PMC97172. 10: Choi MH, Sun HY, Park RY, Kim CM, Bai YH, Kim YR, Rhee JH, Shin SH. Effect of the crp mutation on the utilization of transferrin-bound iron by Vibrio vulnificus. FEMS Microbiol Lett. 2006 Apr;257(2):285-92. PubMed PMID: 16553865. 11: Okujo N, Saito M, Yamamoto S, Yoshida T, Miyoshi S, Shinoda S. Structure of vulnibactin, a new polyamine-containing siderophore from Vibrio vulnificus. Biometals. 1994 Apr;7(2):109-16. PubMed PMID: 8148612. 12: Wen Y, Kim IH, Son JS, Lee BH, Kim KS. Iron and quorum sensing coordinately regulate the expression of vulnibactin biosynthesis in Vibrio vulnificus. J Biol Chem. 2012 Aug 3;287(32):26727-39. doi: 10.1074/jbc.M112.374165. Epub 2012 Jun 13. PubMed PMID: 22696215; PubMed Central PMCID: PMC3411011. 13: Lee HJ, Lee KH. Identification of the fur-binding site in regulatory region of the vulnibactin-receptor gene in Vibrio vulnificus. J Microbiol Biotechnol. 2012 Jan;22(1):46-9. PubMed PMID: 22297218. 14: Pajuelo D, Lee CT, Roig FJ, Lemos ML, Hor LI, Amaro C. Host-nonspecific iron acquisition systems and virulence in the zoonotic serovar of Vibrio vulnificus. Infect Immun. 2014 Feb;82(2):731-44. doi: 10.1128/IAI.01117-13. Epub 2013 Dec 2. PubMed PMID: 24478087; PubMed Central PMCID: PMC3911369. 15: Kim CM, Shin SH. Modulation of iron-uptake systems by a mutation of luxS encoding an autoinducer-2 synthase in Vibrio vulnificus. Biol Pharm Bull. 2011;34(5):632-7. PubMed PMID: 21532149. 16: Mala W, Chomvarin C, Alam M, Rashed SM, Faksri K, Angkititrakul S. Molecular analysis of Vibrio vulnificus isolated from cockles and patients in Thailand. Southeast Asian J Trop Med Public Health. 2014 Jan;45(1):103-12. PubMed PMID: 24964659. 17: Sun HY, Han SI, Choi MH, Kim SJ, Kim CM, Shin SH. Vibrio vulnificus metalloprotease VvpE has no direct effect on iron-uptake from human hemoglobin. J Microbiol. 2006 Oct;44(5):537-47. PubMed PMID: 17082748. 18: Miyoshi S, Inami Y, Moriya Y, Kamei T, Rahman MM, Yamamoto S, Tomochika K, Shinoda S. Characterization of a mutant of Vibrio vulnificus for heme utilization. FEMS Microbiol Lett. 1997 Mar 1;148(1):101-6. PubMed PMID: 9066118. 19: Kim CM, Park RY, Choi MH, Sun HY, Shin SH. Ferrophilic characteristics of Vibrio vulnificus and potential usefulness of iron chelation therapy. J Infect Dis. 2007 Jan 1;195(1):90-8. Epub 2006 Nov 22. PubMed PMID: 17152012. 20: Guerrero-Ferreira RC, Nishiguchi MK. Differential gene expression in bacterial symbionts from loliginid squids demonstrates variation between mutualistic and environmental niches. Environ Microbiol Rep. 2010 Aug 1;2(4):514-523. PubMed PMID: 20680094; PubMed Central PMCID: PMC2911791.