Thiotropocin
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| Category | Antibiotics |
| Catalog number | BBF-03417 |
| CAS | 89550-93-6 |
| Molecular Weight | 212.25 |
| Molecular Formula | C8H4O3S2 |
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Description
Thiotropocin is produced by the strain of Pseudomonas sp. CB-104. It has anti-gram-positive bacteria and negative bacteria, fungi, mycoplasma effect, especially on the proteus, treponema, mycoplasma, and plant pathogenic fungi.
Specification
| Synonyms | BRN 4415507; 4-Hydroxy-8-thioxocyclohept(c)-1,2-oxathiol-3(8H)-one; 8-Mercaptocyclohepta[c][1,2]oxathiole-3,4-dione |
| IUPAC Name | 8-sulfanylcyclohepta[c]oxathiole-3,4-dione |
| Canonical SMILES | C1=CC(=O)C2=C(C(=C1)S)SOC2=O |
| InChI | InChI=1S/C8H4O3S2/c9-4-2-1-3-5(12)7-6(4)8(10)11-13-7/h1-3,12H |
| InChI Key | RWJXTYSZCDAMCD-UHFFFAOYSA-N |
Properties
| Appearance | Orange or Yellow-orange Acicular Crystals |
| Antibiotic Activity Spectrum | Gram-positive bacteria; Gram-negative bacteria; fungi; mycoplasma |
| Boiling Point | 351.5°C at 760 mmHg |
| Density | 1.60 g/cm3 |
Reference Reading
1. Ecology, inhibitory activity, and morphogenesis of a marine antagonistic bacterium belonging to the Roseobacter clade
Jesper Bartholin Bruhn, Kristian Fog Nielsen, Mette Hjelm, Michael Hansen, José Bresciani, Stefan Schulz, Lone Gram Appl Environ Microbiol. 2005 Nov;71(11):7263-70. doi: 10.1128/AEM.71.11.7263-7270.2005.
Roseobacter strain 27-4 has been isolated from a turbot larval rearing unit and is capable of reducing mortality in turbot egg yolk sac larvae. Here, we demonstrate that the supernatant of Roseobacter 27-4 is lethal to the larval pathogens Vibrio anguillarum and Vibrio splendidus in a buffer system and inhibited their growth in marine broth. Liquid chromatography (LC) with both UV spectral detection and high-resolution mass spectrometry (HR-MS) identified the known antibacterial compound thiotropocin or its closely related precursor tropodithietic acid in the bioactive fractions. Antibacterial activity correlated with the appearance of a brownish pigment and was only formed in marine broth under static growth conditions. A thick biofilm of multicellular star-shaped aggregated cells formed at the air-liquid interface under static growth conditions. Here, the bioactive compound was the base peak in the LC-UV chromatograms of the extracts where it constituted 15% of the total peak area. Aerated conditions results in 10-fold-higher cell yield, however, cultures were nonpigmented, did not produce antibacterial activity, and grew as single cells. Production of antibacterial compounds may be quorum regulated, and we identified the acylated homoserine lactone (3-hydroxy-decanoyl homoserine lactone) from cultures of Roseobacter 27-4 using LC-HR-MS. The signal molecule was primarily detected in stagnant cultures. Roseobacter 27-4 grew between 10 and 30 degrees C but died rapidly at 37 degrees C. Also, the antibacterial compounds was sensitive to heat and was inactivated at 37 degrees C in less than 2 days and at 25 degrees C in 8 days. Using Roseobacter 27-4 as a probiotic culture will require that is be established in stagnant or adhered conditions and, due to the temperature sensitivity of the active compound, constant production must be ensured.
2. Biosynthetic Studies of omega-Cycloheptyl Fatty Acids in Alicyclobacillus cycloheptanicus. Formation of Cycloheptanecarboxylic Acid from Phenylacetic Acid
Bradley S. Moore, Kevin Walker, Ingo Tornus, Sandeep Handa, Karl Poralla, Heinz G. Floss J Org Chem. 1997 Apr 4;62(7):2173-2185. doi: 10.1021/jo962402o.
The formation of the structurally novel, mono-substituted cycloheptane ring in omega-cycloheptyl fatty acids in Alicyclobacillus cycloheptanicus (formerly Bacillus cycloheptanicus) has been examined. Feeding experiments with (13)C- and (2)H-labeled intermediates demonstrated that cycloheptanecarboxylic acid (3), probably as its CoA thioester, is the starter unit for omega-cycloheptyl fatty acid biosynthesis. Analysis of the resultant labeling pattern from a feeding experiment with [U-(13)C(6)]glucose suggested a shikimate pathway origin of 3 via aromatic amino acids. [1,2-(13)C(2)]Phenylacetic acid (6) was efficiently metabolized into the 3-derived moiety in a manner reminiscent of the seven-membered ring Pseudomonas metabolite thiotropocin. The fates of the aromatic and benzylic hydrogens of 6 were determined; these dictated various boundary conditions for the biosynthetic pathway from 6 to 3. Taken together with the results from feeding experiments with postulated cycloheptenylcarboxylate biosynthetic intermediates, the data lead us to propose a pathway which involves an oxidative ring-expansion of 6 to a hydroxynorcaradiene intermediate followed by a series of double bond reductions and dehydrations to the saturated 3.
3. Computational studies of the tropone natural products, thiotropocin, tropodithietic acid, and troposulfenin. Significance of thiocarbonyl-enol tautomerism
Edyta M Greer, David Aebisher, Alexander Greer, Ronald Bentley J Org Chem. 2008 Jan 4;73(1):280-3. doi: 10.1021/jo7018416. Epub 2007 Dec 7.
Computations provide insight to the stability and isomeric possibilities of thiotropocin, tropodithietic acid, and troposulfenin. Thiotropocin and tropodithietic acid contain a flat 7-membered ring and delocalized pi-bonds similar to those of tropylium ion (C(7)H(7)(+)). Troposulfenin is far less stable; it contains a puckered tropone ring and localized bonds similar to 1,3,5-cycloheptatriene. A facile 1,5-hydrogen shift suggests that thiotropocin and tropodithietic acid exist as a pair of interconverting tautomers. Loss of an acidic proton from these three tautomers produces the same conjugate base structure.
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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 ╳
