Dioxapyrrolomycin
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| Category | Antibiotics |
| Catalog number | BBF-01160 |
| CAS | 105888-54-8 |
| Molecular Weight | 384.00 |
| Molecular Formula | C12H6N2O4Cl4 |
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Description
It is produced by the strain of Streptomyces sp. MG796-AF7. It mainly has anti-gram-positive bacterial activity.
Specification
| Synonyms | pyrroxamycin; Antibiotic Al-R-2081 |
| IUPAC Name | 2,3-dichloro-5-[(4S)-6,8-dichloro-4H-1,3-benzodioxin-4-yl]-4-nitro-1H-pyrrole |
| Canonical SMILES | C1OC(C2=C(O1)C(=CC(=C2)Cl)Cl)C3=C(C(=C(N3)Cl)Cl)[N+](=O)[O-] |
| InChI | InChI=1S/C12H6Cl4N2O4/c13-4-1-5-10(6(14)2-4)21-3-22-11(5)8-9(18(19)20)7(15)12(16)17-8/h1-2,11,17H,3H2/t11-/m0/s1 |
| InChI Key | CUPRKSFMHRXAFA-NSHDSACASA-N |
Properties
| Appearance | Light Yellow Crystal |
| Antibiotic Activity Spectrum | Gram-posotive becteria |
| Boiling Point | 508.2 °C at 760 mmHg |
| Melting Point | 200-207 °C |
| Density | 1.741 g/cm3 |
| Solubility | Soluble in Methanol, Acetone, Ethyl Acetate; Insoluble in Water |
Reference Reading
1. Investigating the biosynthetic origin of the nitro group in pyrrolomycins
Anokha S Ratnayake, Bradley Haltli, Xidong Feng, Valerie S Bernan, Maya P Singh, Haiyin He, Guy T Carter J Nat Prod. 2008 Nov;71(11):1923-6. doi: 10.1021/np800401h. Epub 2008 Nov 6.
Feasible modes of introducing the nitro group into pyrrolomycin antibiotics were investigated based on incorporation of (15)N-labeled arginine and proline into dioxapyrrolomycin, produced by the actinomycete culture LL-F42248. Biosynthesis of nitrated pyrrolomycins was unaffected by the presence of nitric oxide synthase (NOS) inhibitors. The culture was able to grow in nitrogen-free (minimal) media and produce nitrated secondary metabolites. These results indicate that LL-F42248 is capable of fixing nitrogen.
2. Probing natural product biosynthetic pathways using Fourier transform ion cyclotron resonance mass spectrometry
Xidong Feng, Anokha S Ratnayake, Romila D Charan, Jeffrey E Janso, Valerie S Bernan, Gerhard Schlingmann, Haiyin He, Mark Tischler, Frank E Koehn, Guy T Carter Bioorg Med Chem. 2009 Mar 15;17(6):2154-61. doi: 10.1016/j.bmc.2008.10.073. Epub 2008 Nov 5.
Two natural products, diazepinomicin (1) and dioxapyrrolomycin (2), containing stable isotopic labels of (15)N or deuterium, were used to demonstrate the utility of Fourier transform ion cyclotron resonance mass spectrometry for probing natural product biosynthetic pathways. The isotopic fine structures of significant ions were resolved and subsequently assigned elemental compositions on the basis of highly accurate mass measurements. In most instances the mass measurement accuracy is less than one part per million (ppm), which typically makes the identification of stable-isotope labeling unambiguous. In the case of the mono-(15)N-labeled diazepinomicin (1) derived from labeled tryptophan, tandem mass spectrometry located this (15)N label at the non-amide nitrogen. Through the use of exceptionally high mass resolving power of over 125,000, the isotopic fine structure of the molecular ion cluster of 1 was revealed. Separation of the (15)N(2) peak from the isobaric (13)C(15)N peak, both having similar abundances, demonstrated the presence of a minor amount of doubly (15)N-labeled diazepinomicin (1). Tandem mass spectrometry amplified this isotopic fine structure (Deltam=6.32 mDa) from mDa to 1 Da scale thereby allowing more detailed scrutiny of labeling content and location. Tandem mass spectrometry was also used to assign the location of deuterium labeling in two deuterium-labeled diazepinomicin (1) samples. In one case three deuterium atoms were incorporated into the dibenzodiazepine core; while in the other a mono-D label was mainly incorporated into the farnesyl side chain. The specificity of (15)N-labeling in dioxapyrrolomycin (2) and the proportion of the (15)N-label contained in the nitro group were determined from the measurement of the relative abundance of the (14)NO(2)(1-) and (15)NO(2)(1-) fragment ions.
3. Design, synthesis, and biological evaluation of various α-substituted benzylpyrroles based on the structures of insecticidal chlorfenapyr and natural pyrrolomycins
Qiaoqiao Ma, Yuxiu Liu, Pengxiang Zhang, Yongqiang Li, Lixia Xiong, Qingmin Wang J Agric Food Chem. 2014 Jul 2;62(26):6072-81. doi: 10.1021/jf501377t. Epub 2014 Jun 19.
On the basis of the structures of chlorfenapyr and dioxapyrrolomycin, a series of 2-benzylpyrroles with a hydroxyl, an alkyloxy, an acyloxy, an alkylsulfanyl, or an oxime moiety at the α-position of benzyl were designed and synthesized. Their insecticidal, acaricidal, and fungicidal activities were extensively investigated. The structure-activity relationship showed that benzylpyrroles bearing shorter α-alkyloxy groups gave better activities against most of the insect species; the alkylation of pyrrole usually gave increased activity. Among all compounds, (4-bromo-2-(α-(2,2,2-trifluoroethoxy)-4-chlorobenzyl)-1-(ethoxymethyl)-5-(trifluoromethyl)-1H-pyrrole-3-carbonitrile) (5'j) exhibited the most outstanding insecticidal activities against oriental armyworm (IC₅₀=10 mg L⁻¹), diamondback moth (0.07 mg L⁻¹), corn borer (50 mg L⁻¹), and mosquito (0.04 mg L⁻¹), which are very close to those of chlorfenapyr (5, 0.08, <25, and <0.025 mg L⁻¹, respectively). In addition, some compounds also exhibited a broad or selective fungicidal spectrum.
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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 ╳
