Xanthothricin
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| Category | Antibiotics |
| Catalog number | BBF-03474 |
| CAS | 84-82-2 |
| Molecular Weight | 193.16 |
| Molecular Formula | C7H7N5O2 |
| Purity | >98% by HPLC |
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Description
It is a nitrogenous heterocyclic antibiotic produced by the strain of Str. sp. and Pseudomonas cocovenenans. It has anti-bacterial and mycobacterium effects.
Specification
| Synonyms | Toxoflavin; Toxoflavine; Pyrimido(5,4-e)-1,2,4-triazine-5,7-(1H,6H)-dione, 1,6-dimethyl-; 1-methylreumycin; Fervenuline; GNF-PF-67 |
| Storage | Store at 2-8°C |
| IUPAC Name | 1,6-dimethylpyrimido[5,4-e][1,2,4]triazine-5,7-dione |
| Canonical SMILES | CN1C2=NC(=O)N(C(=O)C2=NC=N1)C |
| InChI | InChI=1S/C7H7N5O2/c1-11-6(13)4-5(10-7(11)14)12(2)9-3-8-4/h3H,1-2H3 |
| InChI Key | SLGRAIAQIAUZAQ-UHFFFAOYSA-N |
| Source | Streptomyces sp. |
Properties
| Appearance | Yellow Acicular Crystal |
| Antibiotic Activity Spectrum | Mycobacteria |
| Boiling Point | 276.7±23.0°C (Predicted) |
| Melting Point | 172-173°C (dec.) |
| Density | 1.65±0.1 g/cm3 (Predicted) |
| Solubility | Soluble in Water (10 mg/mL) |
Reference Reading
1. A novel toxoflavin-quenching regulation in bacteria and its application to resistance cultivars
Jiyeong Park, Okhee Choi, Min Chul Kim, Hyun Jin Chun, Byeongsam Kang, Jinwoo Kim, Yeyeong Lee Microb Biotechnol . 2021 Jul;14(4):1657-1670. doi: 10.1111/1751-7915.13831.
The toxoflavin (Txn), broad host range phytotoxin produced by a variety of bacteria, including Burkholderia glumae, is a key pathogenicity factor of B. glumae in rice and field crops. Two bacteria exhibiting Txn-degrading activity were isolated from healthy rice seeds and identified as Sphingomonas adhaesiva and Agrobacterium sp. respectively. The genes stdR and stdA, encoding proteins responsible for Txn degradation of both bacterial isolates, were identical, indicating that horizontal gene transfer occurred between microbial communities in the same ecosystem. We identified a novel Txn-quenching regulation of bacteria, demonstrating that the LysR-type transcriptional regulator (LTTR) StdR induces the expression of the stdA, which encodes a Txn-degrading enzyme, in the presence of Txn as a coinducer. Here we show that the bacterial StdRTxn-quenching regulatory system mimics the ToxRTxn-mediated biosynthetic regulation of B. glumae. Substrate specificity investigations revealed that Txn is the only coinducer of StdR and that StdA has a high degree of specificity for Txn. Rice plants expressing StdA showed Txn resistance. Collectively, bacteria mimic the mechanism of Txn biosynthesis regulation, employ it in the development of a Txn-quenching regulatory system and share it with neighbouring bacteria for survival in rice environments full of Txn.
2. Synthesis and herbicidal activity of 3-substituted toxoflavin analogs
Jun Suzuki, Ryoya Imaizumi, Tatsuya Hirano, Narihito Ogawa J Pestic Sci . 2021 Aug 20;46(3):278-282. doi: 10.1584/jpestics.D21-010.
We investigated the synthesis and herbicidal activity of 23 toxoflavin analogs,1a-w, in which aromatic rings (R) were introduced into the C-3 position. In paddy field conditions,1k(R=2-CF3-C6H4) and1w(R=2-thienyl) showed excellent herbicidal activity. Under upland field conditions, we found that toxoflavin analogs1a(R=C6H5),1n(R=2-CH3O-C6H4), and1p(R=4-CH3O-C6H4) exhibited wide herbicidal spectrum againstEchinochloa crus-galli (L) var. crus-galli(ECHCG),Chenopodium album, andAmaranthus viridis(AMAVI). The analog with the 2-fluoro group on benzene ring1balso showed high herbicidal activity against both ECHCG and AMAVI.
3. [Structure of the reaction adduct of xanthothricin with acetone]
G G Aleksandrov, S A Dovzhenko, S E Esipov, A I Chernyshev, N A Kliuev Antibiot Khimioter . 1988 Jan;33(1):30-3.
Reaction of xanthothricin demethylation by amines in acetone as a solvent yielded a new compound with a formula of C10H13N5O3. Mass spectrometry, 1H NMR-spectroscopy and x-ray analysis showed that the compound was 4H-1,6-dimethyl-4a(2-oxopropyl)-pyrimido-[5,4-e]-1 ,2,4-triazine-5,7-dione.
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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 ╳
