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MedKoo Cat#: 461309 | Name: Rhizoferrin

Description:

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

Rhizoferrin is a fungal siderophore (microbial iron transport compound).

Chemical Structure

Rhizoferrin
Rhizoferrin
CAS#138846-62-5

Theoretical Analysis

MedKoo Cat#: 461309

Name: Rhizoferrin

CAS#: 138846-62-5

Chemical Formula: C16H24N2O12

Exact Mass: 436.1329

Molecular Weight: 436.37

Elemental Analysis: C, 44.04; H, 5.54; N, 6.42; O, 44.00

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
Rhizoferrin;
IUPAC/Chemical Name
2,2'-((butane-1,4-diylbis(azanediyl))bis(2-oxoethane-2,1-diyl))bis(2-hydroxysuccinic acid)
InChi Key
KUYCNLUJQMRORQ-UHFFFAOYSA-N
InChi Code
InChI=1S/C16H24N2O12/c19-9(5-15(29,13(25)26)7-11(21)22)17-3-1-2-4-18-10(20)6-16(30,14(27)28)8-12(23)24/h29-30H,1-8H2,(H,17,19)(H,18,20)(H,21,22)(H,23,24)(H,25,26)(H,27,28)
SMILES Code
O=C(NCCCCNC(CC(CC(O)=O)(O)C(O)=O)=O)CC(CC(O)=O)(O)C(O)=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
2934.99.03.00
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 436.37 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: Dubey A, Heinonen O. First-principles electronic structure study of rhizoferrin and its Fe(III) complexes. Biometals. 2013 Dec;26(6):1003-12. doi: 10.1007/s10534-013-9677-4. Epub 2013 Sep 25. PubMed PMID: 24065571. 2: Burnside DM, Wu Y, Shafaie S, Cianciotto NP. The Legionella pneumophila Siderophore Legiobactin Is a Polycarboxylate That Is Identical in Structure to Rhizoferrin. Infect Immun. 2015 Oct;83(10):3937-45. doi: 10.1128/IAI.00808-15. Epub 2015 Jul 20. PubMed PMID: 26195554; PubMed Central PMCID: PMC4567642. 3: Matzanke BF, Böhnke R, Möllmann U, Schünemann V, Schumann G, Trautwein AX, Winkelmann G. Transport and utilization of rhizoferrin bound iron in Mycobacterium smegmatis. Biometals. 1999 Dec;12(4):315-21. PubMed PMID: 10816731. 4: Kühn S, Braun V, Köster W. Ferric rhizoferrin uptake into Morganella morganii: characterization of genes involved in the uptake of a polyhydroxycarboxylate siderophore. J Bacteriol. 1996 Jan;178(2):496-504. PubMed PMID: 8550472; PubMed Central PMCID: PMC177684. 5: Thieken A, Winkelmann G. Rhizoferrin: a complexone type siderophore of the Mucorales and entomophthorales (Zygomycetes). FEMS Microbiol Lett. 1992 Jul 1;73(1-2):37-41. PubMed PMID: 1387861. 6: Carrano CJ, Drechsel H, Kaiser D, Jung G, Matzanke B, Winkelmann G, Rochel N, Albrecht-Gary AM. Coordination Chemistry of the Carboxylate Type Siderophore Rhizoferrin: The Iron(III) Complex and Its Metal Analogs. Inorg Chem. 1996 Oct 23;35(22):6429-6436. PubMed PMID: 11666790. 7: Drechsel H, Winkelmann G. The configuration of the chiral carbon atoms in staphyloferrin A and analysis of the transport properties in Staphylococcus aureus. Biometals. 2005 Feb;18(1):75-81. PubMed PMID: 15865412. 8: Yehuda Z, Shenker M, Romheld V, Marschner H, Hadar Y, Chen Y. The Role of Ligand Exchange in the Uptake of Iron from Microbial Siderophores by Gramineous Plants. Plant Physiol. 1996 Nov;112(3):1273-1280. PubMed PMID: 12226445; PubMed Central PMCID: PMC158055. 9: de Locht M, Boelaert JR, Schneider YJ. Iron uptake from ferrioxamine and from ferrirhizoferrin by germinating spores of Rhizopus microsporus. Biochem Pharmacol. 1994 May 18;47(10):1843-50. PubMed PMID: 8204101. 10: Duckworth OW, Akafia MM, Andrews MY, Bargar JR. Siderophore-promoted dissolution of chromium from hydroxide minerals. Environ Sci Process Impacts. 2014 May;16(6):1348-59. doi: 10.1039/c3em00717k. PubMed PMID: 24683601. 11: Kiss K, Liu W, Huntley JF, Norgard MV, Hansen EJ. Characterization of fig operon mutants of Francisella novicida U112. FEMS Microbiol Lett. 2008 Aug;285(2):270-7. doi: 10.1111/j.1574-6968.2008.01237.x. Epub 2008 Jun 18. PubMed PMID: 18564336; PubMed Central PMCID: PMC2770140. 12: Holinsworth B, Martin JD. Siderophore production by marine-derived fungi. Biometals. 2009 Aug;22(4):625-32. doi: 10.1007/s10534-009-9239-y. Epub 2009 Apr 7. PubMed PMID: 19350395; PubMed Central PMCID: PMC2706916. 13: Harris WR, Amin SA, Küpper FC, Green DH, Carrano CJ. Borate binding to siderophores: structure and stability. J Am Chem Soc. 2007 Oct 10;129(40):12263-71. Epub 2007 Sep 13. PubMed PMID: 17850151. 14: Baakza A, Dave BP, Dube HC. Chemical nature, ligand denticity and quantification of fungal siderophores. Indian J Exp Biol. 2004 Jan;42(1):96-105. PubMed PMID: 15274489. 15: Sullivan JT, Jeffery EF, Shannon JD, Ramakrishnan G. Characterization of the siderophore of Francisella tularensis and role of fslA in siderophore production. J Bacteriol. 2006 Jun;188(11):3785-95. PubMed PMID: 16707671; PubMed Central PMCID: PMC1482922. 16: Shenker M, Fan TW, Crowley DE. Phytosiderophores influence on cadmium mobilization and uptake by wheat and barley plants. J Environ Qual. 2001 Nov-Dec;30(6):2091-8. PubMed PMID: 11790018. 17: Zajdowicz S, Haller JC, Krafft AE, Hunsucker SW, Mant CT, Duncan MW, Hodges RS, Jones DN, Holmes RK. Purification and structural characterization of siderophore (corynebactin) from Corynebacterium diphtheriae. PLoS One. 2012;7(4):e34591. doi: 10.1371/journal.pone.0034591. Epub 2012 Apr 13. PubMed PMID: 22514641; PubMed Central PMCID: PMC3326035. 18: Carroll CS, Grieve CL, Murugathasan I, Bennet AJ, Czekster CM, Liu H, Naismith J, Moore MM. The rhizoferrin biosynthetic gene in the fungal pathogen Rhizopus delemar is a novel member of the NIS gene family. Int J Biochem Cell Biol. 2017 Aug;89:136-146. doi: 10.1016/j.biocel.2017.06.005. Epub 2017 Jun 10. PubMed PMID: 28610916. 19: Reissbrodt R, Erler W, Winkelmann G. Iron supply of Pasteurella multocida and Pasteurella haemolytica. J Basic Microbiol. 1994;34(1):61-3. PubMed PMID: 8207666. 20: Pierre JL, Gautier-Luneau I. Iron and citric acid: a fuzzy chemistry of ubiquitous biological relevance. Biometals. 2000 Mar;13(1):91-6. Review. PubMed PMID: 10831230.

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LEO-29102

LEO-29102