Racemomycin C
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| Category | Antibiotics |
| Catalog number | BBF-02170 |
| CAS | 3776-38-3 |
| Molecular Weight | 630.69 |
| Molecular Formula | C25H46N10O9 |
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Description
It is produced by the strain of Str. racemochromogenes 229. It has broad spectrum antibacterial activity and antifungal effect, and it can inhibit PR-8 of influenza virus in tissue culture.
Specification
| Synonyms | Streptothricin E; Yazumycin C; Antibiotic S 15-1B; 2-((O-(Aminocarbonyl)-2-((3-amino-6-((3,6-diamino-1-oxohexyl)amino)-1-oxohexyl)amino)-2-deoxy-beta-D-gulopyranosyl)amino)-1,3a,5,6,7,7a-hexahydro-7-hydroxy-4H-imidazo(4,5-c)pyridin-4-one; BRN 4286375 |
| Storage | Store at -20°C |
| IUPAC Name | [(2R,3R,4S,5R,6R)-6-[[(3aS,7R,7aS)-7-hydroxy-4-oxo-1,3a,5,6,7,7a-hexahydroimidazo[4,5-c]pyridin-2-yl]amino]-5-[[(3S)-3-amino-6-[[(3S)-3,6-diaminohexanoyl]amino]hexanoyl]amino]-4-hydroxy-2-(hydroxymethyl)oxan-3-yl] carbamate |
| Canonical SMILES | C1C(C2C(C(=O)N1)N=C(N2)NC3C(C(C(C(O3)CO)OC(=O)N)O)NC(=O)CC(CCCNC(=O)CC(CCCN)N)N)O |
| InChI | InChI=1S/C25H46N10O9/c26-5-1-3-11(27)7-15(38)30-6-2-4-12(28)8-16(39)32-19-20(40)21(44-24(29)42)14(10-36)43-23(19)35-25-33-17-13(37)9-31-22(41)18(17)34-25/h11-14,17-21,23,36-37,40H,1-10,26-28H2,(H2,29,42)(H,30,38)(H,31,41)(H,32,39)(H2,33,34,35)/t11-,12-,13+,14+,17+,18-,19+,20-,21-,23+/m0/s1 |
| InChI Key | SCHKAKNJXBPJHD-SNQQVPMJSA-N |
Properties
| Appearance | White Hygroscopic Powder |
| Antibiotic Activity Spectrum | fungi; viruses |
| Melting Point | >210°C |
| Density | 1.763 g/cm3 |
Reference Reading
1. Three new 12-carbamoylated streptothricins from Streptomyces sp. I08A 1776
Maoluo Gan, Xudong Zheng, Yufeng Liu, Yan Guan, Chunling Xiao Bioorg Med Chem Lett. 2012 Oct 1;22(19):6151-4. doi: 10.1016/j.bmcl.2012.08.003. Epub 2012 Aug 10.
Two new streptothricins (1 and 2) and a new streptothricin acid derivative (3), all with the carbamoyl group substituted at C-12 of the gulosamine moiety, together with the known N(β)-acetylstreptothricin D acid (4), have been isolated from the culture broth of Streptomyces sp. I08A 1776. The structures of the new compounds were determined by MS, CD, and 1D and 2D NMR spectroscopic data analysis. The isolated compounds were evaluated for antibacterial and antifungal activities. Streptothricin E (6) showed potent activity against the clinically isolated extensively drug-resistant Mycobacterium tuberculosis with MIC values of 0.25-0.5μg/mL.
2. Streptomyces sp. JCK-6131 Protects Plants Against Bacterial and Fungal Diseases via Two Mechanisms
Khanh Duy Le, Jeun Kim, Hoa Thi Nguyen, Nan Hee Yu, Ae Ran Park, Chul Won Lee, Jin-Cheol Kim Front Plant Sci. 2021 Sep 15;12:726266. doi: 10.3389/fpls.2021.726266. eCollection 2021.
Plant bacterial and fungal diseases cause significant agricultural losses and need to be controlled. Beneficial bacteria are promising candidates for controlling these diseases. In this study, Streptomyces sp. JCK-6131 exhibited broad-spectrum antagonistic activity against various phytopathogenic bacteria and fungi. In vitro assays showed that the fermentation filtrate of JCK-6131 inhibited the growth of bacteria and fungi with minimum concentration inhibitory (MIC) values of 0.31-10% and 0.31-1.25%, respectively. In the in vivo experiments, treatment with JCK-6131 effectively suppressed the development of apple fire blight, tomato bacterial wilt, and cucumber Fusarium wilt in a dose-dependent manner. RP-HPLC and ESI-MS/MS analyses indicated that JCK-6131 can produce several antimicrobial compounds, three of which were identified as streptothricin E acid, streptothricin D, and 12-carbamoyl streptothricin D. In addition, the disease control efficacy of the foliar application of JCK-6131 against tomato bacterial wilt was similar to that of the soil drench application, indicating that JCK-6131 could enhance defense resistance in plants. Molecular studies on tomato plants showed that JCK-6131 treatment induced the expression of the pathogenesis-related (PR) genes PR1, PR3, PR5, and PR12, suggesting the simultaneous activation of the salicylate (SA) and jasmonate (JA) signaling pathways. The transcription levels of PR genes increased earlier and were higher in treated plants than in untreated plants following Ralstonia solanacearum infection. These results indicate that Streptomyces sp. JCK-6131 can effectively control various plant bacterial and fungal diseases via two distinct mechanisms of antibiosis and induced resistance.
3. Streptothricin derivatives from Streptomyces sp. I08A 1776
Maoluo Gan, Xudong Zheng, Lishe Gan, Yan Guan, Xueqin Hao, Yishuang Liu, Shuyi Si, Yuqin Zhang, Liyan Yu, Chunling Xiao J Nat Prod. 2011 May 27;74(5):1142-7. doi: 10.1021/np2000733. Epub 2011 Apr 21.
Five new streptothricin derivatives with a carbamoyl group substituted at C-12 (1-5) and three known analogues have been isolated from the culture broth of Streptomyces sp. I08A 1776 by ion exchange and hydrophilic interaction chromatographic techniques. Their structures were determined by spectroscopic and chemical methods. Compound 3 was a streptothricin derivative possessing a cis-streptolidine moiety. Its absolute configuration was defined by comparison of quantum chemical TDDFT calculated and experimental ECD spectra. Compound 5 and streptothricin E (6) displayed antibacterial and antifungal activity with MIC values in the range 1-64 μg/mL.
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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 ╳
