Cyclothiocurvularin A
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| Category | Others |
| Catalog number | BBF-04758 |
| CAS | |
| Molecular Weight | 410.44 |
| Molecular Formula | C19H22O8S |
| Purity | >95% by HPLC |
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Description
Cycuriocurvularin is a 12-membered macrolide isolated from Penicillium and Curvularia sp.
Specification
| Storage | Store at -20°C |
| IUPAC Name | (3R,4S,7R,11S)-4,17,19-trihydroxy-11-methyl-2,13-dioxo-12-oxa-6-thiatricyclo[13.4.0.03,7]nonadeca-1(15),16,18-triene-4-carboxylic acid |
| Canonical SMILES | CC1CCCC2C(C(=O)C3=C(CC(=O)O1)C=C(C=C3O)O)C(CS2)(C(=O)O)O |
| InChI | InChI=1S/C19H22O8S/c1-9-3-2-4-13-16(19(26,8-28-13)18(24)25)17(23)15-10(6-14(22)27-9)5-11(20)7-12(15)21/h5,7,9,13,16,20-21,26H,2-4,6,8H2,1H3,(H,24,25)/t9-,13+,16-,19-/m0/s1 |
| InChI Key | CATXBXDAUWOWMZ-FEDPDIOBSA-N |
Properties
| Solubility | Soluble in methanol, DMSO |
Reference Reading
1. Condensation of Macrocyclic Polyketides Produced by Penicillium sp. DRF2 with Mercaptopyruvate Represents a New Fungal Detoxification Pathway
Marcos V de Castro, Laura P Ióca, David E Williams, et al. J Nat Prod. 2016 Jun 24;79(6):1668-78. doi: 10.1021/acs.jnatprod.6b00295. Epub 2016 May 26.
Application of a refined procedure of experimental design and chemometric analysis to improve the production of curvularin-related polyketides by a marine-derived Penicillium sp. DRF2 resulted in the isolation and identification of cyclothiocurvularins 6-8 and cyclosulfoxicurvularins 10 and 11, novel curvularins condensed with a mercaptolactate residue. Two additional new curvularins, 3 and 4, are also reported. The structures of the sulfur-bearing curvularins were unambiguously established by analysis of spectroscopic data and by X-ray diffraction analysis. Analysis of stable isotope feeding experiments with [U-(13)C3(15)N]-l-cysteine confirmed the presence of the 2-hydroxy-3-mercaptopropanoic acid residue in 6-8 and the oxidized sulfoxide in 10 and 11. Cyclothiocurvularins A (6) and B (7) are formed by spontaneous reaction between 10,11-dehydrocurvularin (2) and mercaptopyruvate (12) obtained by transamination of cysteine. High ratios of [U-(13)C3(15)N]-l-cysteine incorporation into cyclothiocurvularin B (7), the isolation of two diastereomers of cyclothiocurvularins, the lack of cytotoxicity of cyclothiocurvularin B (7) and its methyl ester (8), and the spontaneous formation of cyclothiocurvularins from 10,11-dehydrocurvularin and mercaptopyruvate provide evidence that the formation of cyclothiocurvularins may well correspond to a 10,11-dehydrocurvularin detoxification process by Penicillium sp. DRF2.
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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 ╳
