Telomycin
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| Category | Antibiotics |
| Catalog number | BBF-03497 |
| CAS | 19246-24-3 |
| Molecular Weight | 1272.32 |
| Molecular Formula | C59H77N13O19 |
| Purity | >98% |
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Description
Telomycin is an ester peptide antibiotic produced by Str. canus C-159. It has activity against gram-positive bacteria.
Specification
| Synonyms | A 128-HYP, A 128-OP |
| Storage | Store at -20°C |
| IUPAC Name | (2S)-2-amino-4-[[(2S)-1-[[(3S,6S,12S,13S,21S,24S,27S,28R,31S,32R)-13,32-dihydroxy-24-[(1S)-1-hydroxyethyl]-3-[(1S)-1-hydroxy-2-methylpropyl]-6-[1-(1H-indol-3-yl)ethyl]-9-(1H-indol-3-ylmethylidene)-21,28-dimethyl-2,5,8,11,17,20,23,26,30-nonaoxo-29-oxa-1,4,7,10,16,19,22,25-octazatricyclo[29.3.0.012,16]tetratriacontan-27-yl]amino]-3-hydroxy-1-oxopropan-2-yl]amino]-4-oxobutanoic acid |
| Canonical SMILES | CC1C(C(=O)NC(C(=O)NC(C(=O)NCC(=O)N2CCC(C2C(=O)NC(=CC3=CNC4=CC=CC=C43)C(=O)NC(C(=O)NC(C(=O)N5CCC(C5C(=O)O1)O)C(C(C)C)O)C(C)C6=CNC7=CC=CC=C76)O)C)C(C)O)NC(=O)C(CO)NC(=O)CC(C(=O)O)N |
| InChI | InChI=1S/C59H77N13O19/c1-25(2)49(79)46-57(87)72-18-16-40(76)48(72)59(90)91-29(6)45(69-52(82)38(24-73)65-41(77)20-34(60)58(88)89)55(85)68-44(28(5)74)54(84)64-27(4)50(80)63-23-42(78)71-17-15-39(75)47(71)56(86)66-37(19-30-21-61-35-13-9-7-11-31(30)35)51(81)67-43(53(83)70-46)26(3)33-22-62-36-14-10-8-12-32(33)36/h7-14,19,21-22,25-29,34,38-40,43-49,61-62,73-76,79H,15-18,20,23-24,60H2,1-6H3,(H,63,80)(H,64,84)(H,65,77)(H,66,86)(H,67,81)(H,68,85)(H,69,82)(H,70,83)(H,88,89)/t26?,27-,28-,29+,34-,38-,39-,40+,43-,44-,45-,46-,47-,48-,49-/m0/s1 |
| InChI Key | FJEKCPBQVANMTA-GRZFNQFESA-N |
| Source | Streptomyces sp. |
Properties
| Appearance | Colorless Solid |
| Antibiotic Activity Spectrum | Gram-positive bacteria |
| Boiling Point | 1760.9°C at 760 mmHg |
| Density | 1.5 g/cm3 |
| Solubility | Soluble in ethanol, methanol, DMF, DMSO |
Reference Reading
1. Micromonospora schwarzwaldensis sp. nov., a producer of telomycin, isolated from soil
Maria Soledad Vela Gurovic, Sandor Nietzsche, Nicole Domin, Ivana Seccareccia, Sebastian Müller, Karin Martin, Markus Nett Int J Syst Evol Microbiol . 2013 Oct;63(Pt 10):3812-3817. doi: 10.1099/ijs.0.051623-0.
A Gram-stain-positive, spore-forming actinomycete strain (HKI0641(T)) was isolated from a soil sample collected in the Black Forest, Germany. During screening for antimicrobial natural products this bacterium was identified as a producer of the antibiotic telomycin. Morphological characteristics and chemotaxonomic data indicated that the strain belonged to the genus Micromonospora. The peptidoglycan of strain HKI0641(T) contained meso-diaminopimelic acid, and the fatty acid profile consisted predominantly of anteiso-C15 : 0, iso-C15 : 0, iso-C16 : 0 and C16 : 0. MK-10(H4), MK-10(H2) and MK-10 were identified as the major menaquinones. To determine the taxonomic positioning of strain HKI0641(T), we computed a binary tanglegram of two rooted phylogenetic trees that were based upon 16S rRNA and gyrB gene sequences. The comparative analysis of the two common classification methods strongly supported the phylogenetic affiliation with the genus Micromonospora, but it also revealed discrepancies in the assignment at the level of the genomic species. 16S rRNA gene sequence analysis identified Micromonospora coxensis DSM 45161(T) (99.1 % sequence similarity) and Micromonospora marina DSM 45555(T) (99.0 %) as the nearest taxonomic neighbours, whereas the gyrB sequence of strain HKI0641(T) indicated a closer relationship to Micromonospora aurantiaca DSM 43813(T) (95.1 %). By means of DNA-DNA hybridization experiments, it was possible to resolve this issue and to clearly differentiate strain HKI0641(T) from other species of the genus Micromonospora. The type strains of the aforementioned species of the genus Micromonospora could be further distinguished from strain HKI0641(T) by several phenotypic properties, such as colony colour, NaCl tolerance and the utilization of carbon sources. The isolate was therefore assigned to a novel species of the genus Micromonospora, for which the name Micromonospora schwarzwaldensis sp. nov. is proposed. The type strain is HKI0641(T) ( = DSM 45708(T) = CIP 110415(T)).
2. Streptomyces coeruleorubidus as a potential biocontrol agent for Newcastle disease virus
Hanaa A El-Samadony, Rewan Abdelaziz, Shimaa A Amer, Marwa M Gado, Yasmine H Tartor, Ahmed B Barakat, Gamal El-Didamony BMC Vet Res . 2022 Jun 24;18(1):241. doi: 10.1186/s12917-022-03349-7.
Background:Newcastle disease virus (NDV) is a severe disease that affects domestic and wild birds. Controlled antibiotics derived from probiotics have been examined as prospective solutions for preserving seroconversion in NDV-vaccinated fowl. In this study, the secondary metabolite "telomycin" was extracted from Streptomyces coeruleorubidus (S. coeruleorubidus) isolated from Egypt's cultivated soil. The structure of telomycin was determined by the elucidation of spectroscopic analysis, including nuclear magnetic resonance (NMR) and mass spectrometry (MS) spectra, and comparison with the literature. The antiviral activity of the secondary metabolite was tested by checking its effect on NDV hemagglutination activity (HA). Moreover, HA of NDV was tested after inoculation of NDV (control) and a combination of telomycin and NDV in 10- days- specific pathogen-free embryonated chicken eggs (SPF-ECE) daily candling. Histopathological examination was performed for chorioallantoic membranes and liver of SPF-ECE.Results:S. coeruleorubidus secondary metabolite "telomycin" showed complete hemagglutination inhibition (HI) activity of NDV strain (MN635617) with log106infectivity titers (EID50/mL). The HA of NDV strain was 8 log2and 9 log2with 0.5% and 0.75% of chicken RBCs, respectively. Preserved structures of chorioallantoic-membranes (CAM) with dilated capillary networks were observed in the treated group inoculated with telomycin and NDV. Histological changes in SPF-ECE liver were examined after inoculation in ova to further characterize the telomycin effect. Telomycin and NDV mixture inoculated group showed preserved cytoarchitecture of hepatocytes with the presence of perivascular foci of lymphocytes. The group that was inoculated with telomycin alone showed normal histology of hepatic acini, central veins, and portal triads.Conclusion:S. coeruleorubidus telomycin is a promising bioactive agent that might be a biological weapon against a deadly chicken NDV that costs farmers a lot of money.
3. Draft Genome Sequence of Streptomyces canus ATCC 12647, a Producer of Telomycin
Dennis Y Liu, Nathan A Magarvey, Yongchang Li Genome Announc . 2016 Mar 24;4(2):e00173-16. doi: 10.1128/genomeA.00173-16.
We present here the genome sequence ofStreptomyces canusATCC 12647, a producer of the antibiotic telomycin, noted for its unique antibacterial activity against cardiolipin. Genomic analysis using the bioinformatics tool PRISM revealed the presence of multiple biosynthetic gene clusters, including those for telomycin and other natural products of potential pharmacological interest.
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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
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Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
