Tirandamycin BCAS# 60587-14-6 |
Quality Control & MSDS
3D structure
Package In Stock
Number of papers citing our products
| Cas No. | 60587-14-6 | SDF | Download SDF |
| PubChem ID | 54679289 | Appearance | Powder |
| Formula | C22H27NO8 | M.Wt | 433.46 |
| Type of Compound | Alkaloids | Storage | Desiccate at -20°C |
| Solubility | Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc. | ||
| Chemical Name | (3E)-3-[(2E,4E)-1-hydroxy-6-[2-(hydroxymethyl)-1,7-dimethyl-5-oxo-3,9,10-trioxatricyclo[4.3.1.02,4]decan-8-yl]-4-methylhepta-2,4-dienylidene]pyrrolidine-2,4-dione | ||
| SMILES | CC1C2C(=O)C3C(O3)(C(O2)(OC1C(C)C=C(C)C=CC(=C4C(=O)CNC4=O)O)C)CO | ||
| Standard InChIKey | LYJKREGDQDJIDC-BHHJBWQLSA-N | ||
| Standard InChI | InChI=1S/C22H27NO8/c1-10(5-6-13(25)15-14(26)8-23-20(15)28)7-11(2)17-12(3)18-16(27)19-22(9-24,31-19)21(4,29-17)30-18/h5-7,11-12,17-19,24-25H,8-9H2,1-4H3,(H,23,28)/b6-5+,10-7+,15-13+ | ||
| General tips | For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months. We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months. Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it. |
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| About Packaging | 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial. 2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial. 3. Try to avoid loss or contamination during the experiment. |
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| Shipping Condition | Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request. | ||
| Description | 1. Tirandamycin B is a BmAsnRS inhibitor. 2. Tirandamycin B is a leading anti-filarial drug . 3. Tirandamycin B has antitumor and antibacterial activities. |
| Targets | Antifection |
Tirandamycin B Dilution Calculator
Tirandamycin B Molarity Calculator
| 1 mg | 5 mg | 10 mg | 20 mg | 25 mg | |
| 1 mM | 2.307 mL | 11.5351 mL | 23.0702 mL | 46.1404 mL | 57.6754 mL |
| 5 mM | 0.4614 mL | 2.307 mL | 4.614 mL | 9.2281 mL | 11.5351 mL |
| 10 mM | 0.2307 mL | 1.1535 mL | 2.307 mL | 4.614 mL | 5.7675 mL |
| 50 mM | 0.0461 mL | 0.2307 mL | 0.4614 mL | 0.9228 mL | 1.1535 mL |
| 100 mM | 0.0231 mL | 0.1154 mL | 0.2307 mL | 0.4614 mL | 0.5768 mL |
| * Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations. | |||||
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Metabiolic products of microorganisms. Tirandamycin B(author's transl).[Pubmed:962473]
Arch Microbiol. 1976 Aug;109(1-2):65-74.
Streptomyces flaveolus, strain Tu 1240 produces besides Tirandamycin A, a hitherto unknown antibiotic, which is closely related to Tirandamycin A. The new antibiotic Tirandamycin B contains one additional hydroxylgroup. Both antibiotics exhibit a similar antimicrobial spectrum and they seem to have the same mechanism of action. According to the data obtained from mass spectrometry, 13C-and 1H-NMR spectra formula II could be deduced for Tirandamycin B.
Discovery of a new family of Dieckmann cyclases essential to tetramic acid and pyridone-based natural products biosynthesis.[Pubmed:25621700]
Org Lett. 2015 Feb 6;17(3):628-31.
Bioinformatic analyses indicate that TrdC, SlgL, LipX2, KirHI, and FacHI belong to a group of highly homologous proteins involved in biosynthesis of actinomycete-derived Tirandamycin B, streptolydigin, alpha-lipomycin, kirromycin, and factumycin, respectively. However, assignment of their biosynthetic roles has remained elusive. Gene inactivation and complementation, in vitro biochemical assays with synthetic analogues, point mutations, and phylogenetic tree analyses reveal that these proteins represent a new family of Dieckmann cyclases that drive tetramic acid and pyridone scaffold biosynthesis.
Medium optimization of Streptomyces sp. 17944 for tirandamycin B production and isolation and structural elucidation of tirandamycins H, I and J.[Pubmed:23715040]
J Antibiot (Tokyo). 2014 Jan;67(1):127-32.
We have recently isolated tirandamycin (TAM) B from Streptomyces sp. 17944 as a Brugia malayi AsnRS (BmAsnRS) inhibitor that efficiently kills the adult B. malayi parasites and does not exhibit general cytotoxicity to human hepatic cells. We now report (i) the comparison of metabolite profiles of S. sp. 17944 in six different media, (ii) identification of a medium enabling the production of TAM B as essentially the sole metabolite, and with improved titer, and (iii) isolation and structural elucidation of three new TAM congeners. These findings shed new insights into the structure-activity relationship of TAM B as a BmAsnRS inhibitor, highlighting the delta-hydroxymethyl-alpha,beta-epoxyketone moiety as the critical pharmacophore, and should greatly facilitate the production and isolation of sufficient quantities of TAM B for further mechanistic and preclinical studies to advance the candidacy of TAM B as an antifilarial drug lead. The current study also serves as an excellent reminder that traditional medium and fermentation optimization should continue to be very effective in improving metabolite flux and titer.
