Desotamide
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| Category | Antibiotics |
| Catalog number | BBF-04589 |
| CAS | 194660-14-5 |
| Molecular Weight | 696.84 |
| Molecular Formula | C35H52N8O7 |
| Purity | >95% by HPLC |
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Description
It is a cyclic hexapeptide antibiotic first isolated from streptomyces sp. It was found to produce Salinamide A, an inhibitor of bacterial RNA polymerase. It has activity against S. aureus, S. pneumoniae and methicillin-resistant S. epidermidis.
Specification
| Synonyms | Cyclo(L-alloisoleucyl-L-asparaginylglycyl-L-tryptophyl-L-leucyl-D-leucyl); cyclo[L-asparagyl-glycyl-L-tryptophyl-L-leucyl-D-leucyl-L-alloisoleucyl]; Desotamide A |
| Storage | Store at -20°C |
| IUPAC Name | 2-[(2S,8S,11S,14R,17S)-17-[(2R)-butan-2-yl]-8-(1H-indol-3-ylmethyl)-11,14-bis(2-methylpropyl)-3,6,9,12,15,18-hexaoxo-1,4,7,10,13,16-hexazacyclooctadec-2-yl]acetamide |
| Canonical SMILES | CCC(C)C1C(=O)NC(C(=O)NCC(=O)NC(C(=O)NC(C(=O)NC(C(=O)N1)CC(C)C)CC(C)C)CC2=CNC3=CC=CC=C32)CC(=O)N |
| InChI | InChI=1S/C35H52N8O7/c1-7-20(6)30-35(50)42-27(15-28(36)44)31(46)38-17-29(45)39-26(14-21-16-37-23-11-9-8-10-22(21)23)33(48)40-24(12-18(2)3)32(47)41-25(13-19(4)5)34(49)43-30/h8-11,16,18-20,24-27,30,37H,7,12-15,17H2,1-6H3,(H2,36,44)(H,38,46)(H,39,45)(H,40,48)(H,41,47)(H,42,50)(H,43,49)/t20-,24+,25-,26+,27+,30+/m1/s1 |
| InChI Key | LJGXNPVJAKBNOK-DTWKRICWSA-N |
| Source | Streptomyces sp. |
Properties
| Appearance | White Lyophilisate |
| Antibiotic Activity Spectrum | Bacteria |
| Boiling Point | 1171.4±65.0°C at 760 mmHg |
| Density | 1.1±0.1 g/cm3 |
| Solubility | Soluble in Ethanol, Methanol, DMF, DMSO; Poorly soluble in Water |
Reference Reading
1. Deep Sea Actinomycetes and Their Secondary Metabolites
Kui Hong, Manita Kamjam, Zinxin Deng, Periyasamy Sivalingam Front Microbiol . 2017 May 1;8:760. doi: 10.3389/fmicb.2017.00760.
Deep sea is a unique and extreme environment. It is a hot spot for hunting marine actinomycetes resources and secondary metabolites. The novel deep sea actinomycete species reported from 2006 to 2016 including 21 species under 13 genera with the maximum number fromMicrobacterium, followed byDermacoccus, StreptomycesandVerrucosispora, and one novel species for the other 9 genera. Eight genera of actinomycetes were reported to produce secondary metabolites, among whichStreptomycesis the richest producer. Most of the compounds produced by the deep sea actinomycetes presented antimicrobial and anti-cancer cell activities. Gene clusters related to biosynthesis of desotamide, heronamide, and lobophorin have been identified from the deep sea derivedStreptomyces.
2. Identification of the Biosynthetic Gene Cluster for the Anti-infective Desotamides and Production of a New Analogue in a Heterologous Host
Jianhua Ju, Qinglian Li, Yongxiang Song, Aijun Sun, Xiangjing Qin, Xing Zhang J Nat Prod . 2015 Apr 24;78(4):944-8. doi: 10.1021/acs.jnatprod.5b00009.
The desotamides (DSAs) are potent antibacterial cyclohexapeptides produced by Streptomyces scopuliridis SCSIO ZJ46. We have identified the 39-kb dsa biosynthetic gene cluster by whole-genome scanning. Composed of 17 open reading frames, the cluster codes for four nonribosomal peptide synthetases and associated resistance, transport, regulatory, and precursor biosynthesis proteins. Heterologous expression of the dsa gene cluster in S. coelicolor M1152 afforded desotamides A and B and the new desotamide G. Cluster identification and its demonstrated amenability to heterologous expression provide the foundation for future mechanistic studies as well as the generation of new and potentially clinically significant DSA analogues.
3. Cyclic Hexapeptides from the Deep South China Sea-Derived Streptomyces scopuliridis SCSIO ZJ46 Active Against Pathogenic Gram-Positive Bacteria
Weimin Zhang, Jianhua Ju, Yongxiang Song, Qinglian Li, Jingren Zhang, Aijun Sun, Xue Liu, Yuchan Chen, Yun Zhang J Nat Prod . 2014 Aug 22;77(8):1937-41. doi: 10.1021/np500399v.
Three new cyclohexapeptides, desotamides B-D (2-4), and the known desotamide (1) were isolated from marine microbe Streptomyces scopuliridis SCSIO ZJ46. The sequences and absolute configurations of 2-4 were elucidated on the basis of high-resolution spectroscopic data, Marfey's method, and chiral-phase HPLC data. Desotamide C (3) contains a unique N-formyl-kynurenine residue, whereas 4 lacks formylation at the same site. Compounds 1 and 2 displayed notable antibacterial activities against strains of Streptococcus pnuemoniae, Staphylococcus aureus, and methicillin-resistant Staphylococcus epidermidis (MRSE), and structure activity relationship studies revealed the indispensability of the Trp component for antibacterial activity within this new scaffold.
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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 ╳
