Resomycin C
* Please be kindly noted products are not for therapeutic use. We do not sell to patients.
| Category | Antibiotics |
| Catalog number | BBF-02180 |
| CAS | |
| Molecular Weight | 362.33 |
| Molecular Formula | C21H14O6 |
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Description
It is produced by the strain of Streptomyces sp. GW71/2497. Resomycin C showed activity of anti-staphylococcus aureus, Escherichia coli and Streptomyces green, with MIC of about 20 μg/mL.
Specification
| IUPAC Name | methyl 5,7-dihydroxy-2-methyl-6,11-dioxotetracene-1-carboxylate |
| Canonical SMILES | CC1=C(C2=CC3=C(C(=C2C=C1)O)C(=O)C4=C(C3=O)C=CC=C4O)C(=O)OC |
| InChI | InChI=1S/C21H14O6/c1-9-6-7-10-12(15(9)21(26)27-2)8-13-17(19(10)24)20(25)16-11(18(13)23)4-3-5-14(16)22/h3-8,22,24H,1-2H3 |
| InChI Key | ITFQAKHLOKEJNL-UHFFFAOYSA-N |
Properties
| Appearance | Orange Solid |
Reference Reading
1. An NADPH-Dependent Ketoreductase Catalyses the Tetracyclic to Pentacyclic Skeletal Rearrangement in Chartreusin Biosynthesis
Fang Wen Jiao, Yi Shuang Wang, Xue Ting You, Wanqing Wei, Yu Chen, Cheng Long Yang, Zhi Kai Guo, Bo Zhang, Yong Liang, Ren Xiang Tan, Rui Hua Jiao, Hui Ming Ge Angew Chem Int Ed Engl. 2021 Dec 6;60(50):26378-26384. doi: 10.1002/anie.202112047. Epub 2021 Nov 5.
Redox tailoring enzymes play key roles in generating structural complexity and diversity in type II polyketides. In chartreusin biosynthesis, the early 13 C-labeling experiments and bioinformatic analysis suggest the unusual aglycone is originated from a tetracyclic anthracyclic polyketide. Here, we demonstrated that the carbon skeleton rearrangement from a linear anthracyclic polyketide to an angular pentacyclic biosynthetic intermediate requires two redox enzymes. The flavin-dependent monooxygenase ChaZ catalyses a Baeyer-Villiger oxidation on resomycin C to form a seven-membered lactone. Subsequently, a ketoreductase ChaE rearranges the carbon skeleton and affords the α-pyrone containing pentacyclic intermediate in an NADPH-dependent manner via tandem reactions including the reduction of the lactone carbonyl group, Aldol-type reaction, followed by a spontaneous γ-lactone ring formation, oxidation and aromatization. Our work reveals an unprecedented function of a ketoreductase that contributes to generate structural complexity of aromatic polyketide.
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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 ╳
