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MedKoo Cat#: 535084 | Name: Agrobactin

Description:

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

Agrobactin is an iron transport compound (siderophore) from Agrobacterium tumefaciens.

Chemical Structure

Agrobactin
Agrobactin
CAS#70393-50-9

Theoretical Analysis

MedKoo Cat#: 535084

Name: Agrobactin

CAS#: 70393-50-9

Chemical Formula: C32H36N4O10

Exact Mass: 636.2431

Molecular Weight: 636.66

Elemental Analysis: C, 60.37; H, 5.70; N, 8.80; O, 25.13

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
Agrobactin
IUPAC/Chemical Name
4-Oxazolecarboxamide, N-(4-((2,3-dihydroxybenzoyl)amino)butyl)-N-(3-((2,3-dihydroxybenzoyl)amino)propyl)-2-(2,3-dihydroxyphenyl)-4,5-dihydro-5-methyl-, (4S-trans)-
InChi Key
BWPMKVHHFNGYEN-CJAUYULYSA-N
InChi Code
InChI=1S/C32H36N4O10/c1-18-25(35-31(46-18)21-10-6-13-24(39)28(21)42)32(45)36(17-7-15-34-30(44)20-9-5-12-23(38)27(20)41)16-3-2-14-33-29(43)19-8-4-11-22(37)26(19)40/h4-6,8-13,18,25,37-42H,2-3,7,14-17H2,1H3,(H,33,43)(H,34,44)/t18-,25+/m1/s1
SMILES Code
O=C([C@H]1N=C(C2=CC=CC(O)=C2O)O[C@@H]1C)N(CCCCNC(C3=CC=CC(O)=C3O)=O)CCCNC(C4=CC=CC(O)=C4O)=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 636.66 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: Ong SA, Peterson T, Neilands JB. Agrobactin, a siderophore from Agrobacterium tumefaciens. J Biol Chem. 1979 Mar 25;254(6):1860-5. PMID: 33987. 2: Leong SA, Neilands JB. Relationship of siderophore-mediated iron assimilation to virulence in crown gall disease. J Bacteriol. 1981 Aug;147(2):482-91. PMID: 6455414; PMCID: PMC216068. 3: Datta B, Chakrabartty PK. Siderophore biosynthesis genes of Rhizobium sp. isolated from Cicer arietinum L. 3 Biotech. 2014 Aug;4(4):391-401. doi: 10.1007/s13205-013-0164-y. Epub 2013 Sep 5. PMID: 28324476; PMCID: PMC4145622. 4: Sonoda H, Suzuki K, Yoshida K. Gene cluster for ferric iron uptake in Agrobacterium tumefaciens MAFF301001. Genes Genet Syst. 2002 Jun;77(3):137-46. doi: 10.1266/ggs.77.137. PMID: 12207035. 5: 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. 6: López-Goñi I, Moriyón I, Neilands JB. Identification of 2,3-dihydroxybenzoic acid as a Brucella abortus siderophore. Infect Immun. 1992 Nov;60(11):4496-503. PMID: 1398964; PMCID: PMC258194. 7: Minnick AA, McKee JA, Dolence EK, Miller MJ. Iron transport-mediated antibacterial activity of and development of resistance to hydroxamate and catechol siderophore-carbacephalosporin conjugates. Antimicrob Agents Chemother. 1992 Apr;36(4):840-50. doi: 10.1128/aac.36.4.840. PMID: 1503447; PMCID: PMC189448. 8: Griffiths GL, Sigel SP, Payne SM, Neilands JB. Vibriobactin, a siderophore from Vibrio cholerae. J Biol Chem. 1984 Jan 10;259(1):383-5. PMID: 6706943. 9: Yoganathan S, Sit CS, Vederas JC. Chemical synthesis and biological evaluation of gallidermin-siderophore conjugates. Org Biomol Chem. 2011 Apr 7;9(7):2133-41. doi: 10.1039/c0ob00846j. Epub 2011 Feb 3. PMID: 21290068. 10: Annamalai R, Jin B, Cao Z, Newton SM, Klebba PE. Recognition of ferric catecholates by FepA. J Bacteriol. 2004 Jun;186(11):3578-89. doi: 10.1128/JB.186.11.3578-3589.2004. PMID: 15150246; PMCID: PMC415739. 11: Peter HH. Eisenchelierung. Biologische Bedeutung und medizinische Anwendungen [Iron chelation. Biological significance and medical application]. Schweiz Med Wochenschr. 1983 Oct 8;113(40):1428-33. German. PMID: 6227988. 12: Miller MC, Parkin S, Fetherston JD, Perry RD, Demoll E. Crystal structure of ferric-yersiniabactin, a virulence factor of Yersinia pestis. J Inorg Biochem. 2006 Sep;100(9):1495-500. doi: 10.1016/j.jinorgbio.2006.04.007. Epub 2006 May 3. PMID: 16806483. 13: Sciortino CV, Byers BR, Cox P. Evaluation of iron-chelating agents in cultured heart muscle cells. Identification of a potential drug for chelation therapy. J Lab Clin Med. 1980 Dec;96(6):1081-5. PMID: 7430764. 14: Thulasiraman P, Newton SM, Xu J, Raymond KN, Mai C, Hall A, Montague MA, Klebba PE. Selectivity of ferric enterobactin binding and cooperativity of transport in gram-negative bacteria. J Bacteriol. 1998 Dec;180(24):6689-96. PMID: 9852016; PMCID: PMC107775. 15: Page WJ, Dale PL. Stimulation of Agrobacterium tumefaciens Growth by Azotobacter vinelandii Ferrisiderophores. Appl Environ Microbiol. 1986 Feb;51(2):451-4. PMID: 16347002; PMCID: PMC238895. 16: Sprencel C, Cao Z, Qi Z, Scott DC, Montague MA, Ivanoff N, Xu J, Raymond KM, Newton SM, Klebba PE. Binding of ferric enterobactin by the Escherichia coli periplasmic protein FepB. J Bacteriol. 2000 Oct;182(19):5359-64. doi: 10.1128/jb.182.19.5359-5364.2000. PMID: 10986237; PMCID: PMC110977. 17: Bergeron RJ, Weimar WR. Kinetics of iron acquisition from ferric siderophores by Paracoccus denitrificans. J Bacteriol. 1990 May;172(5):2650-7. doi: 10.1128/jb.172.5.2650-2657.1990. PMID: 2185228; PMCID: PMC208909. 18: Deryło M, Skorupska A. Biological activity of rhizobial siderophore. Acta Microbiol Pol. 1991;40(3-4):265-8. PMID: 1726625. 19: Lodge JS, Gaines CG, Arceneaux JE, Byers BR. Ferrisiderophore reductase activity in Agrobacterium tumefaciens. J Bacteriol. 1982 Feb;149(2):771-4. PMID: 7056702; PMCID: PMC216571.