Prothracarcin
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| Category | Antibiotics |
| Catalog number | BBF-02067 |
| CAS | 81542-99-6 |
| Molecular Weight | 226.27 |
| Molecular Formula | C14H14N2O |
| Purity | >98% |
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Description
Prothracarcin is an antitumor antibiotic produced by Str. umbrosus subsp. raffinophilus DO-62. It is active against Gram-positive and Gram-negative bacteria and experimental murine tumor sarcoma 180 and leukemia P388.
Specification
| Synonyms | Antibiotic DC 62 |
| Storage | Store at -20°C |
| IUPAC Name | (6aS,8E)-8-ethylidene-7,9-dihydro-6aH-pyrrolo[2,1-c][1,4]benzodiazepin-11-one |
| Canonical SMILES | CC=C1CC2C=NC3=CC=CC=C3C(=O)N2C1 |
| InChI | InChI=1S/C14H14N2O/c1-2-10-7-11-8-15-13-6-4-3-5-12(13)14(17)16(11)9-10/h2-6,8,11H,7,9H2,1H3/b10-2+/t11-/m0/s1 |
| InChI Key | GYUDGZRJHSDPLH-KJQCOJPZSA-N |
Properties
| Appearance | Crystal |
| Antibiotic Activity Spectrum | Gram-positive bacteria; Gram-negative bacteria; neoplastics (Tumor) |
| Boiling Point | 432.2°C at 760 mmHg |
| Melting Point | 85-87°C (dec.) |
| Density | 1.22 g/cm3 |
| Solubility | Soluble in DMSO, methol |
Reference Reading
1. Prothracarcin, a novel antitumor antibiotic
K Shimizu, I Kawamoto, F Tomita, M Morimoto, K Fujimoto J Antibiot (Tokyo). 1982 Aug;35(8):972-8. doi: 10.7164/antibiotics.35.972.
A novel antibiotic, prothracarcin was isolated from the culture broth of Streptomyces umbrosus subsp. raffinophilus DO-62. The antibiotic has the molecular formula of C14H14N2O and belongs to the pyrrolo [1,4]benzodiazepine antibiotics. Its structure has been elucidated by mass and NMR spectra. It is active against Gram-positive and Gram-negative bacteria and experimental murine tumor sarcoma 180 and leukemia P388.
2. Limazepines A-F, pyrrolo[1,4]benzodiazepine Antibiotics from an Indonesian Micrococcus sp
Serge Fotso, T Mark Zabriskie, Philip J Proteau, Patricia M Flatt, Dwi Andreas Santosa, Taifo Mahmud J Nat Prod. 2009 Apr;72(4):690-5. doi: 10.1021/np800827w.
In our screening of Indonesian microorganisms for novel bioactive natural products we have isolated seven new compounds, designated as limazepines A, B1 and B2 (isolated as an isomeric mixture), C, D, E, and F, from the culture broth of Micrococcus sp. strain ICBB 8177. In addition, the known natural products prothracarcin and 7-O-succinylmacrolactin A, as well as two previously reported synthetic compounds, 2-amino-3-hydroxy-4-methoxybenzoic acid methyl ester and 4-ethylpyrrole-2-carboxaldehyde, were obtained from the extract. Chemical structures were determined by spectroscopic methods and by comparison with the NMR data of structurally related compounds. The limazepines belong to the growing group of the pyrrolo[1,4]benzodiazepine antitumor antibiotics isolated from various soil bacteria. Limazepines B1/B2 mixture, C, and E were active against the Gram-positive bacterium Staphylococcus aureus and the Gram-negative bacterium Escherichia coli. Limazepine D was also active against S. aureus, but was not active against E. coli. Interestingly, only the limazepines B1/B2 mixture and D were active against Pseudomonas aeruginosa.
3. Stereoselective Olefination with Sterically Demanding Julia-Kocienski Reagents: Total Synthesis of Oxo-prothracarcin, Oxo-tomaymycin, and Boseongazepine B
Zigma Rs Leitis, Guna Sakaine, Artis Kine Ns, Gints Smits ACS Omega. 2022 Aug 17;7(34):30519-30534. doi: 10.1021/acsomega.2c03732. eCollection 2022 Aug 30.
Total syntheses of three pyrrolo[1,4]benzodiazepine anticancer antibiotic family members oxo-prothracarcin, oxo-tomaymycin, and boseongazepine B are described. The total syntheses feature late-stage stereoselective olefination employing modified Julia-Kocienski reagents that can be conveniently prepared in only two steps and allows for a significant reduction in the number of linear steps. Detailed density functional theory (DFT) studies explain the stereochemical outcome of the key step.
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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 ╳
