(S)-Dihydroaeruginoic acid
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| Category | Bioactive by-products |
| Catalog number | BBF-04226 |
| CAS | 143209-04-5 |
| Molecular Weight | 223.25 |
| Molecular Formula | C10H9NO3S |
| Purity | >98% by HPLC |
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Description
It is a simple aromatic siderophore produced by several species of pseudomonas. It exhibits antibacterial, antifungal and antitumor activity.
Specification
| Synonyms | (4S)-4,5-Dihydro-2-(2-hydroxyphenyl)-4-thiazolecarboxylic Acid; CGP 52547; (S)-4,5-Dihydro-2-(2-hydroxyphenyl)-4-thiazolecarboxylic Acid; (+)-(S)-Dihydroaeruginoic Acid; (+)-Dihydroaeruginoic acid; 4-Thiazolecarboxylic acid, 4,5-dihydro-2-(2-hydroxyphenyl)-, (S)-; 4-Thiazolecarboxylic acid, 4,5-dihydro-2-(2-hydroxyphenyl)-, (4S)-; (S)-2-(2-Hydroxyphenyl)-4,5-dihydrothiazole-4-carboxylic acid; (4S)-Dihydroaeruginoic acid |
| Storage | Store at -20°C |
| IUPAC Name | (4S)-2-(2-hydroxyphenyl)-4,5-dihydro-1,3-thiazole-4-carboxylic acid |
| Canonical SMILES | C1C(N=C(S1)C2=CC=CC=C2O)C(=O)O |
| InChI | InChI=1S/C10H9NO3S/c12-8-4-2-1-3-6(8)9-11-7(5-15-9)10(13)14/h1-4,7,12H,5H2,(H,13,14)/t7-/m1/s1 |
| InChI Key | CECDPVOEINSAQG-SSDOTTSWSA-N |
| Source | Pseudomonas aeruginosa |
Properties
| Appearance | Yellow to Tan Solid |
| Antibiotic Activity Spectrum | Neoplastics (Tumor); Fungi; Bacterial |
| Boiling Point | 466.3±55.0°C at 760 mmHg |
| Density | 1.51±0.1 g/cm3 |
| Solubility | Soluble in Ethanol, Methanol, DMF, DMSO |
Reference Reading
1. (+)-(S)-dihydroaeruginoic acid, an inhibitor of Septoria tritici and other phytopathogenic fungi and bacteria, produced by Pseudomonas fluorescens
R Carmi, E Levy, F J Gough, S Carmeli J Nat Prod . 1994 Sep;57(9):1200-5. doi: 10.1021/np50111a002.
Three antibiotics were isolated from a CH2Cl2 extract of the liquid culture of Pseudomonas fluorescens strain PFM2. Two of the antibiotics were identified as 2,4-diacetylphloroglucinol and pyoluterin. The structure elucidation, absolute stereochemistry, synthesis, and biological activities of the new antibiotic (+)-(S)- dihydroaeruginoic acid [1] are reported.
2. Pyochelin Biosynthetic Metabolites Bind Iron and Promote Growth in Pseudomonads Demonstrating Siderophore-like Activity
William M Wuest, Djamaladdin G Musaev, Anna R Kaplan ACS Infect Dis . 2021 Mar 12;7(3):544-551. doi: 10.1021/acsinfecdis.0c00897.
Pseudomonadsemploy several strategies to sequester iron vital for their survival including the use of siderophores such as pyoverdine and pyochelin. Similar in structure but significantly less studied are pyochelin biosynthetic byproducts, dihydroaeruginoic acid, aeruginoic acid, aeruginaldehyde (IQS), and aeruginol, along with two other structurally related molecules, aerugine and pyonitrins A-D, which have all been isolated from numerousPseudomonadextracts. Because of the analogous substructure of these compounds to pyochelin, we hypothesized that they may play a role in iron homeostasis or have a biological effect on other bacterial species. Herein, we discuss the physiochemical evaluation of these molecules and disclose, for the first time, their ability to bind iron and promote growth inPseudomonads.
3. Dihydroaeruginoic acid synthetase and pyochelin synthetase, products of the pchEF genes, are induced by extracellular pyochelin in Pseudomonas aeruginosa
Cornelia Reimmann, Dieter Haa, Markus Beyeler, Laura Serino Microbiology (Reading) . 1998 Nov;144 ( Pt 11):3135-3148. doi: 10.1099/00221287-144-11-3135.
The siderophore pyochelin of Pseudomonas aeruginosa is derived from one molecule of salicylate and two molecules of cysteine. Two cotranscribed genes, pchEF, encoding peptide synthetases have been identified and characterized. pchE was required for the conversion of salicylate to dihydroaeruginoate (Dha), the condensation product of salicylate and one cysteine residue and pchF was essential for the synthesis of pyochelin from Dha. The deduced PchE (156 kDa) and PchF (197 kDa) proteins had adenylation, thiolation and condensation/cyclization motifs arranged as modules which are typical of those peptide synthetases forming thiazoline rings. The pchEF genes were coregulated with the pchDCBA operon, which provides enzymes for the synthesis (PchBA) and activation (PchD) of salicylate as well as a putative thioesterase (PchC). Expression of a translational pchE'-'lacZ fusion was strictly dependent on the PchR regulator and was induced by extracellular pyochelin, the end product of the pathway. Iron replete conditions led to Fur (ferric uptake regulator)-dependent repression of the pchE'-'lacZ fusion. A translational pchD'-'lacZ fusion was also positively regulated by PchR and pyochelin and repressed by Fur and iron. Thus, autoinduction by pyochelin (or ferric pyochelin) and repression by iron ensure a sensitive control of the pyochelin pathway in P. aeruginosa.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
