Scorodonin
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| Category | Antibiotics |
| Catalog number | BBF-02888 |
| CAS | 74660-77-8 |
| Molecular Weight | 142.58 |
| Molecular Formula | C7H7ClO |
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Description
It is produced by the strain of Marasmius scorodonius. It has anti-bacterial, Streptomyces and fungal effects. In vitro it inhibits DNA-dependent RNA polymerases with IC50 of 25 μg/mL.
Specification
| Synonyms | (R)-7-Chloro-2,3-heptadien-5-yn-1-ol; 2,3-Heptadien-5-yn-1-ol, 7-chloro-, (R)- |
| IUPAC Name | (2R)-7-chlorohepta-2,3-dien-5-yn-1-ol |
| Canonical SMILES | C(C=C=CC#CCCl)O |
| InChI | InChI=1S/C7H7ClO/c8-6-4-2-1-3-5-7-9/h1,5,9H,6-7H2 |
| InChI Key | BRBJAAXWYUMXBE-UHFFFAOYSA-N |
Properties
| Appearance | Yellowish Oily Matter |
| Antibiotic Activity Spectrum | Gram-negative bacteria; Fungi |
| Boiling Point | 260.5°C at 760 mmHg |
| Density | 1.109 g/cm3 |
| Solubility | Soluble in Ethanol, Methanol, Chloroform |
Reference Reading
1. Enantioselective Allenation of Terminal Alkynes Catalyzed by Copper Halides of Mixed Oxidation States and Its Application to the Total Synthesis of Scorodonin
Guolin Wu, Yuan Yao, Gen Li, Xue Zhang, Hui Qian, Shengming Ma Angew Chem Int Ed Engl. 2022 Jan 21;61(4):e202112427. doi: 10.1002/anie.202112427. Epub 2021 Dec 15.
Naturally occurring conjugated allenynes are of general interest owing to their potent and various biological activities. The 1,5-H transfer of alka-1,4-diyn-3-yl amines would be one of the most straightforward yet challenging approaches to such compounds since, in principle, two regioisomers may be formed involving two C-C triple bonds. Herein, a catalytic recipe of copper halides with mixed oxidation states, i.e., CuCl/CuBr2 , has been identified to address the issues of the side reaction of conjugate addition and the selectivity of 1,5-H transfer of alka-1,4-diyn-3-yl amines in EATA (enantioselective allenation of terminal alkynes) reaction involving 2-alkynals. This method provided various allenynes with excellent enantioselectivities, and was also applied to the first highly enantioselective total synthesis of natural product scorodonin. Mechanistic studies and DFT calculations elucidated the regioselectivity for the observed 1,5-H transfer.
2. Synthesis of the structure proposed for the natural allenic antibiotic scorodonin
Ya-Jun Jian, Yikang Wu Org Biomol Chem. 2010 Apr 21;8(8):1905-9. doi: 10.1039/c000481b.
The structure proposed for scorodonin, a natural allenyne with significant antibacterial and antifungal activities, was synthesized through an enantioselective route. The spectroscopic data of the synthetic allenyne are generally consistent with those reported for the natural one, but slight yet definite differences were observed in (13)C NMR.
3. Antibiotics from basidiomycetes. X. Scorodonin, a new antibacterial and antifungal metabolite from Marasmius scorodonius (Fr.) Fr
T Anke, J Kupka, G Schramm, W Steglich J Antibiot (Tokyo). 1980 May;33(5):463-7. doi: 10.7164/antibiotics.33.463.
Scorodonin (1), a novel biologically active metabolite, was isolated from submerged cultures of the mushroom Marasmius scorodonius (FR.) FR. Its structure has been determined by chemical and physical methods. The antibiotic inhibits the growth of bacteria, yeasts, and filamentous fungi. In cells of the ascitic form of EHRLICH carcinoma the incorporation of thymidine and uridine into DNA and RNA is strongly inhibited by scorodonin whereas the incorporation of leucine into protein is not affected.
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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 ╳
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