Azotochelin | CAS#23369-85-9 | siderophore

MedKoo Cat#: 597543 | Name: Azotochelin

Description:

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

Azotochelin is a siderophore produced by Azotobacter vinelandii, functioning as an iron-chelating compound that facilitates iron acquisition under iron-limited conditions. Structurally, it consists of two catecholate groups, enabling high-affinity Fe(III) binding. Bioactivity studies indicate that azotochelin exhibits an Fe(III) binding constant (log β) in the range of ~30–32, comparable to other microbial siderophores like enterobactin but with lower overall stability. It promotes iron uptake in A. vinelandii and supports nitrogen fixation by maintaining iron homeostasis. Unlike some other siderophores, azotochelin does not exhibit strong antimicrobial activity but plays a crucial ecological role in microbial competition and symbiotic plant interactions.

Chemical Structure

Azotochelin

CAS#23369-85-9

Theoretical Analysis

MedKoo Cat#: 597543

Name: Azotochelin

CAS#: 23369-85-9

Chemical Formula: C20H22N2O8

Exact Mass: 418.1376

Molecular Weight: 418.40

Elemental Analysis: C, 57.41; H, 5.30; N, 6.70; O, 30.59

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

Azotochelin; ISD-I 207; ISD-I-207; ISD-I207; ISDI 207; ISDI-207; ISDI207;

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

Instruction

View handling instruction

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.

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

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PMID: 37428843; PMCID: PMC10394670. 4: Srivastava S, Dong H, Baars O, Sheng Y. Bioavailability of mineral-associated trace metals as cofactors for nitrogen fixation by Azotobacter vinelandii. Geobiology. 2023 Jul;21(4):507-519. doi: 10.1111/gbi.12552. Epub 2023 Feb 27. PMID: 36852450. 5: Southwell JW, Herman R, Raines DJ, Clarke JE, Böswald I, Dreher T, Gutenthaler SM, Schubert N, Seefeldt J, Metzler-Nolte N, Thomas GH, Wilson KS, Duhme-Klair AK. Siderophore-Linked Ruthenium Catalysts for Targeted Allyl Ester Prodrug Activation within Bacterial Cells. Chemistry. 2023 Feb 7;29(8):e202202536. doi: 10.1002/chem.202202536. Epub 2022 Dec 21. PMID: 36355416; PMCID: PMC10108276. 6: Baranska NG, Parkin A, Duhme-Klair AK. Electrochemical and Solution Structural Characterization of Fe(III) Azotochelin Complexes: Examining the Coordination Behavior of a Tetradentate Siderophore. Inorg Chem. 2022 Dec 5;61(48):19172-19182. doi: 10.1021/acs.inorgchem.2c02777. Epub 2022 Oct 17. 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FEMS Microbiol Lett. 2003 Nov 21;228(2):211-6. doi: 10.1016/S0378-1097(03)00753-5. PMID: 14638426. 14: 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. doi: 10.1128/AEM.66.4.1580-1586.2000. PMID: 10742245; PMCID: PMC92026. 15: Cornish AS, Page WJ. The catecholate siderophores of Azotobacter vinelandii: their affinity for iron and role in oxygen stress management. Microbiology (Reading). 1998 Jul;144(7):1747-1754. doi: 10.1099/00221287-144-7-1747. PMID: 33757230. 16: 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. doi: 10.1023/a:1009266705308. PMID: 9450313. 17: Huyer M, Page WJ. Zn Increases Siderophore Production in Azotobacter vinelandii. 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