Azotochelin

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

Hodoodo CAT#: H597543

CAS#: 23369-85-9

Description: Azotochelin is a siderophore from Azotobacter vinelandii.


Chemical Structure

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Azotochelin
CAS# 23369-85-9

Theoretical Analysis

Hodoodo Cat#: H597543
Name: Azotochelin
CAS#: 23369-85-9
Chemical Formula: C20H22N2O8
Exact Mass: 418.14
Molecular Weight: 418.400
Elemental Analysis: C, 57.41; H, 5.30; N, 6.70; O, 30.59

Price and Availability

This product is not in stock, which may be available by custom synthesis. For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge). Quote less than 1g will not be provided. To request quote, please email to sales @hodoodo.com or click below button.
Note: Price will be listed if it is available in the future.

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Synonym: Azotochelin;

IUPAC/Chemical Name: N2,N6-bis(2,3-dihydroxybenzoyl)-L-lysine

InChi Key: KQPFLOCEYZIIRD-ZDUSSCGKSA-N

InChi Code: InChI=1S/C20H22N2O8/c23-14-8-3-5-11(16(14)25)18(27)21-10-2-1-7-13(20(29)30)22-19(28)12-6-4-9-15(24)17(12)26/h3-6,8-9,13,23-26H,1-2,7,10H2,(H,21,27)(H,22,28)(H,29,30)/t13-/m0/s1

SMILES Code: O=C(O)[C@H](CCCCNC(C1=CC=CC(O)=C1O)=O)NC(C2=CC=CC(O)=C2O)=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:

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 418.40 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
Formulation protocol:
In vitro protocol:
In vivo protocol:

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1: Bellenger JP, Arnaud-Neu F, Asfari Z, Myneni SC, Stiefel EI, Kraepiel AM. Complexation of oxoanions and cationic metals by the biscatecholate siderophore azotochelin. J Biol Inorg Chem. 2007 Mar;12(3):367-76. Epub 2006 Dec 14. PubMed PMID: 17171370.

2: Bellenger JP, Wichard T, Kraepiel AM. Vanadium requirements and uptake kinetics in the dinitrogen-fixing bacterium Azotobacter vinelandii. Appl Environ Microbiol. 2008 Mar;74(5):1478-84. doi: 10.1128/AEM.02236-07. Epub 2008 Jan 11. PubMed PMID: 18192412; PubMed Central PMCID: PMC2258613.

3: Cornish AS, Page WJ. Role of molybdate and other transition metals in the accumulation of protochelin by Azotobacter vinelandii. Appl Environ Microbiol. 2000 Apr;66(4):1580-6. PubMed PMID: 10742245; PubMed Central PMCID: PMC92026.

4: Knosp O, von Tigerstrom M, Page WJ. Siderophore-mediated uptake of iron in Azotobacter vinelandii. J Bacteriol. 1984 Jul;159(1):341-7. PubMed PMID: 6429124; PubMed Central PMCID: PMC215635.

5: Shi D, Xu Y, Hopkinson BM, Morel FM. Effect of ocean acidification on iron availability to marine phytoplankton. Science. 2010 Feb 5;327(5966):676-9. doi: 10.1126/science.1183517. Epub 2010 Jan 14. PubMed PMID: 20075213.

6: Page WJ, Kwon E, Cornish AS, Tindale AE. The csbX gene of Azotobacter vinelandii encodes an MFS efflux pump required for catecholate siderophore export. FEMS Microbiol Lett. 2003 Nov 21;228(2):211-6. PubMed PMID: 14638426.

7: Huyer M, Page WJ. Zn Increases Siderophore Production in Azotobacter vinelandii. Appl Environ Microbiol. 1988 Nov;54(11):2625-31. PubMed PMID: 16347766; PubMed Central PMCID: PMC204346.

8: Deicke M, Bellenger JP, Wichard T. Direct quantification of bacterial molybdenum and iron metallophores with ultra-high-performance liquid chromatography coupled to time-of-flight mass spectrometry. J Chromatogr A. 2013 Jul 12;1298:50-60. doi: 10.1016/j.chroma.2013.05.008. Epub 2013 May 10. PubMed PMID: 23726243.

9: Möllmann U, Ghosh A, Dolence EK, Dolence JA, Ghosh M, Miller MJ, Reissbrodt R. Selective growth promotion and growth inhibition of gram-negative and gram-positive bacteria by synthetic siderophore-beta-lactam conjugates. Biometals. 1998 Jan;11(1):1-12. PubMed PMID: 9450313.

10: Page WJ, Huyer M. Derepression of the Azotobacter vinelandii siderophore system, using iron-containing minerals to limit iron repletion. J Bacteriol. 1984 May;158(2):496-502. PubMed PMID: 6233258; PubMed Central PMCID: PMC215455.

11: Page WJ, Patrick J. The DNA gyrase inhibitors, nalidixic acid and oxolinic acid, prevent iron-mediated repression of catechol siderophore synthesis in Azotobacter vinelandii. Biol Met. 1988;1(1):57-61. PubMed PMID: 2856355.

12: Wilde EJ, Hughes A, Blagova EV, Moroz OV, Thomas RP, Turkenburg JP, Raines DJ, Duhme-Klair AK, Wilson KS. Interactions of the periplasmic binding protein CeuE with Fe(III) n-LICAM(4-) siderophore analogues of varied linker length. Sci Rep. 2017 Apr 6;7:45941. doi: 10.1038/srep45941. PubMed PMID: 28383577; PubMed Central PMCID: PMC5382913.