Depsidomycin
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| Category | Antibiotics |
| Catalog number | BBF-01362 |
| CAS | 131956-33-7 |
| Molecular Weight | 791.98 |
| Molecular Formula | C38H65N9O9 |
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Description
It is produced by the strain of Streptomyces lavendofoliae M1951-61F2. Depsidomycin has weak antibacterial activity and immunosuppressive effect.
Specification
| Synonyms | Antibiotic MI 951-65F2 |
| IUPAC Name | 2-formamido-3-methyl-N-[20-methyl-3,16-bis(2-methylpropyl)-2,5,12,15,18,22-hexaoxo-13-propan-2-yl-21-oxa-1,4,10,11,14,17,27-heptazatricyclo[21.4.0.06,11]heptacosan-19-yl]pentanamide |
| Canonical SMILES | CCC(C)C(C(=O)NC1C(OC(=O)C2CCCNN2C(=O)C(NC(=O)C3CCCNN3C(=O)C(NC(=O)C(NC1=O)CC(C)C)C(C)C)CC(C)C)C)NC=O |
| InChI | InChI=1S/C38H65N9O9/c1-10-23(8)30(39-19-48)34(51)45-31-24(9)56-38(55)28-14-12-16-41-47(28)36(53)26(18-21(4)5)43-33(50)27-13-11-15-40-46(27)37(54)29(22(6)7)44-32(49)25(17-20(2)3)42-35(31)52/h19-31,40-41H,10-18H2,1-9H3,(H,39,48)(H,42,52)(H,43,50)(H,44,49)(H,45,51) |
| InChI Key | QCUFYOBGGZSFHY-UHFFFAOYSA-N |
Properties
| Appearance | White Crystalline |
| Antibiotic Activity Spectrum | neoplastics (Tumor) |
| Melting Point | 272-274°C |
Reference Reading
1. Total synthesis of a depsidomycin analogue by convergent solid-phase peptide synthesis and macrolactonization strategy for antitubercular activity
Venugopala K Narayanaswamy, Fernando Albericio, Yacoob Mohamed Coovadia, Hendrik G Kruger, Glenn E M Maguire, Melendhran Pillay, Thavendran Govender J Pept Sci. 2011 Oct;17(10):683-9. doi: 10.1002/psc.1389. Epub 2011 Jul 18.
Depsidomycin is a cyclic heptadepsi-peptide isolated from the cultured broth of Streptomyces lavendofoliae MI951-62F2. It exhibits significant antimicrobial and immunosuppressive activity. The total synthesis of a depsidomycin analogue in which 1,2-piperazine-3-carboxylic acid was substituted with proline is described. After several trials using different strategies, the desired depsidomycin analogue was obtained via stepwise synthesis starting by the amino acid 'head' and macrolactonization under Yamaguchi conditions. The cyclic depsipeptide was evaluated to have an minimum inhibitory concentration (MIC) of 4 µg/ml against H37RV and 16 µg/ml against MDR clinical strains of MTB (MDR-MTB), while the linear precursor 8 also had MICs of 4 and 16 µg/ml for the susceptible and resistant strains, respectively.
2. Depsidomycins B and C: New Cyclic Peptides from a Ginseng Farm Soil-Derived Actinomycete
Yun Kwon, Woong Sub Byun, Byung-Yong Kim, Myoung Chong Song, Munhyung Bae, Yeo Joon Yoon, Jongheon Shin, Sang Kook Lee, Dong-Chan Oh Molecules. 2018 May 25;23(6):1266. doi: 10.3390/molecules23061266.
LC/MS-based chemical profiling of a ginseng farm soil-derived actinomycete strain, Streptomyces sp. BYK1371, enabled the discovery of two new cyclic heptapeptides, depsidomycins B and C (1 and 2), each containing two piperazic acid units and a formyl group at their N-terminus. The structures of 1 and 2 were elucidated by a combination of spectroscopic and chemical analyses. These new compounds were determined to possess d-leucine, d-threonine, d-valine, and S-piperazic acid based on the advanced Marfey's method and a GITC (2,3,4,6-tetra-O-acetyl-β-d-glucopyranosyl isothiocyanate) derivatization of their hydrolysates, followed by LC/MS analysis. Depsidomycins B and C displayed significant antimetastatic activities against metastatic breast cancer cells (MDA-MB-231).
3. Identifying protein kinase inhibitors using an assay based on inhibition of aerial hyphae formation in Streptomyces
Barbara Waters, Geeta Saxena, Yangsheng Wanggui, David Kau, Stephen Wrigley, Richard Stokes, Julian Davies J Antibiot (Tokyo). 2002 Apr;55(4):407-16. doi: 10.7164/antibiotics.55.407.
We have identified a strain of Streptomyces in which aerial hyphae formation appears to be especially sensitive to inhibition by protein kinase inhibitors. Using this assay, a number of bacterial cultures have been screened and novel inhibitors of eukaryotic protein kinases have been identified. Since M. tuberculosis possesses multiple eukaryotic-like protein kinase genes, we tested the active kinase inhibitors for the inhibition of mycobacterial growth and obtained several potent compounds. This identifies a new biochemical class of antimycobacterial agents.
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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 ╳
