Reumycin
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| Category | Antibiotics |
| Catalog number | BBF-02187 |
| CAS | 5016-18-2 |
| Molecular Weight | 179.14 |
| Molecular Formula | C6H5N5O2 |
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Description
It is originally isolated from Act. sp. Reumycin is toxic to Airy carcinoma, sarcoma-180, sarcoma-37, lymphosarcoma and other tumor cells.
Specification
| Synonyms | Reumitsin; Rheumygin; 1-demethyltoxoflavin; NSC 99733; 6-Methylpyrimido(5,4-e)-as-triazine-5,7(1H,6H)-dione |
| IUPAC Name | 6-methyl-8H-pyrimido[5,4-e][1,2,4]triazine-5,7-dione |
| Canonical SMILES | CN1C(=O)C2=C(NC1=O)N=NC=N2 |
| InChI | InChI=1S/C6H5N5O2/c1-11-5(12)3-4(9-6(11)13)10-8-2-7-3/h2H,1H3,(H,9,10,13) |
| InChI Key | ZLLAXLPOOMLVRF-UHFFFAOYSA-N |
Properties
| Appearance | Yellow Crystalline |
| Antibiotic Activity Spectrum | neoplastics (Tumor) |
| Melting Point | 244-245°C |
| Density | 1.544 g/cm3 |
Reference Reading
1. [Study of alkaline hydrolysis of reumycin using NMR spectroscopy]
S V Shorshneva, S E Esipov, A I Chernyshev Antibiot Med Biotekhnol. 1987 Feb;32(2):116-20.
The transformation sequence of reumycin in aqueous (D2O) solutions with various pD was studied by NMR spectroscopy and the structures of the yielding products were determined. It was shown that formation of 6-(3-methylureido)-1,2,4-triazine-5-carboxylic acid was the first stage of reumycin alkaline hydrolysis. The subsequent cyclization of this compound resulted in obtaining 5-methyl-5H-imidazo [4,5-e]-1,2,4-triazin-6 (7H) one-4a-carboxylic acid in mono-,di- or trianionic form which depended on the medium pH and was due to dissociation of the carboxylic group, N(4)H group of the triazine ring and N(7)H group of the imidazolidinone ring.
2. Characterization of the N-methyltransferases involved in the biosynthesis of toxoflavin, fervenulin and reumycin from Streptomyces hiroshimensis ATCC53615
Can Su, Yijun Yan, Xiaowei Guo, Jianying Luo, Chongxi Liu, Zhouxin Zhang, Wen-Sheng Xiang, Sheng-Xiong Huang Org Biomol Chem. 2019 Jan 16;17(3):477-481. doi: 10.1039/c8ob02847h.
Toxoflavin (1), fervenulin (2), and reumycin (3), known to be produced by plant pathogen Burkholderia glumae BGR1, are structurally related 7-azapteridine antibiotics. Previous biosynthetic studies revealed that N-methyltransferase ToxA from B. glumae BGR1 catalyzed the sequential methylation at N6 and N1 in pyrimido[5,4-e]-as-triazine-5,7(6H,8H)-dione (4) to generate 1. However, the N8 methylation of 4 in the biosynthesis of fervenulin remains unclear. To explore the N-methyltransferases required for the biosynthesis of 1 and 2, we identified and characterized the fervenulin and toxoflavin biosynthetic gene clusters in S. hiroshimensis ATCC53615. On the basis of the structures of intermediates accumulated from the four N-methyltransferase gene inactivation mutants and systematic enzymatic methylation reactions, the tailoring steps for the methylation order in the biosynthesis of 1 and 2 were proposed. The N-methylation order and routes for the biosynthesis of fervenulin and toxoflavin in S. hiroshimensis are more complex and represent an obvious departure from those in B. glumae BGR1.
3. [Structure and physicochemical properties of isolated molecules of reumycin]
G G Sheina, S E Esipov, A Iu Ivanov, S G Stepan'ian Antibiot Med Biotekhnol. 1987 Feb;32(2):111-5.
IR and electron spectra of an uracil derivative (antitumor antibiotic reumycin) were studied by low temperature spectroscopy. The experimental data corresponded to the quantum chemistry calculations of electron transmission. On the basis of the spectra interpretation the molecular structure of the reumycin isolated molecules was suggested. pKa of reumycin in aqueous medium was determined by UV spectroscopy.
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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 ╳
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