Fervenulin
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| Category | Antibiotics |
| Catalog number | BBF-00923 |
| CAS | 483-57-8 |
| Molecular Weight | 193.16 |
| Molecular Formula | C7H7N5O2 |
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Description
Fervenulin is a nitrogen-containing heterocyclic antibiotic produced by Streptomyces fervens. It has anti-Gram-positive bacteria activity, weak anti-Gram-negative bacteria and mycobacterial activity, and anti-mutant and trichomonas activity.
Specification
| Synonyms | Planomycin; Fervenuline; Pulanomycin |
| IUPAC Name | 6,8-dimethylpyrimido[5,4-e][1,2,4]triazine-5,7-dione |
| Canonical SMILES | CN1C2=C(C(=O)N(C1=O)C)N=CN=N2 |
| InChI | InChI=1S/C7H7N5O2/c1-11-5-4(8-3-9-10-5)6(13)12(2)7(11)14/h3H,1-2H3 |
| InChI Key | RRTKVYSLIGQWCO-UHFFFAOYSA-N |
Properties
| Appearance | Yellow Crystal |
| Antibiotic Activity Spectrum | Gram-positive bacteria; Gram-negative bacteria; mycobacteria; parasites |
| Boiling Point | 417.2°C at 760 mmHg |
| Melting Point | 178-179°C(dec.) |
| Density | 1.474 g/cm3 |
| Solubility | Soluble in water, methanol, acetone, chloroform |
Reference Reading
1. Synthesis and properties of mesoionic pyrimido[1,2-b-a1pyridazine-2,4-diones and mesoionic pyridazino[2,3-a-a1-s-trizine-2,4-diones: mesoionic analogs structurally related to fervenulin
R A Carapellotti, R A Coburn J Pharm Sci . 1976 Oct;65(10):1505-10. doi: 10.1002/jps.2600651022.
Derivatives of two new and unusual classes of heterocycles, possessing structural similarities to the broad spectrum antibiotic fervenulin, were synthesized and examined for in vitro antimicrobial activity. Only three of 17 mesoionic pyrimido[1,2-b]pyridazine-2,4-diones exhibited evidence of antimicrobial activity while seven of eight mesoionic pyridazino[2,3-a]-s-triazine-2,4-diones were active against one or more microorganisms. Susceptibility toward attack by nucleophiles of both mesoionic pyridazino[2,3-a]-s-triazine-2,4-diones and fervenulin was observed.
2. Characterization of the N-methyltransferases involved in the biosynthesis of toxoflavin, fervenulin and reumycin from Streptomyces hiroshimensis ATCC53615
Chongxi Liu, Sheng-Xiong Huang, Can Su, Xiaowei Guo, Jianying Luo, Wen-Sheng Xiang, Zhouxin Zhang, Yijun Yan 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. [X-ray structural study of the pyrimido-[5,4-e]-1,2,4-triazine antibiotics xanthothricin and fervenulin]
S E Esipov, G G Aleksandrov Antibiot Med Biotekhnol . 1986 Mar;31(3):181-4.
The structures of xanthothricin (I) and fervenulin (II), pyrimido-[5,4-e]-1,2,4-triazine antibiotics were determined by x-ray analysis. The crystals of I and II are monoclinic: a 9.667(6), 18.270(7), b 14.029(9), 5.723(2), c 6.914(3), 18.058(7) A, beta 116.47(3), 118.90(2) degrees, Z 4,8; space group P21/c. Analysis of bond length distribution in I and II was indicative of significant alternation of the double and ordinary bonds.
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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 ╳
