Cervinomycin A2
* Please be kindly noted products are not for therapeutic use. We do not sell to patients.
| Category | Antibiotics |
| Catalog number | BBF-03479 |
| CAS | 82658-22-8 |
| Molecular Weight | 527.48 |
| Molecular Formula | C29H21NO9 |
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Description
It is produced by the strain of Amycolata autotrophica. It has anti-gram-positive bacteria (MIC is 0.04-0.12 μg/mL) and weak anti-Saccharomyces cerevisiae (MIC is 100 μg/mL) activity.
Specification
| Synonyms | Antibiotic 167B; Antibiotic 4181A; (1)Benzopyrano(2',3':6,7)naphth(2,1-g)oxazolo(3,2-b)isoquinoline-8,14,15,17-tetrone, 1,2,3a,4-tetrahydro-11,12-dimethoxy-16-hydroxy-3a-methyl-, (-)-; Cerubinomycin A2; 167-B |
| IUPAC Name | 3-hydroxy-23,24-dimethoxy-10-methyl-9,20-dioxa-6-azaheptacyclo[15.12.0.02,14.04,12.06,10.019,28.021,26]nonacosa-1(17),2,4(12),13,15,19(28),21,23,25-nonaene-5,18,27,29-tetrone |
| Canonical SMILES | CC12CC3=C(C(=C4C(=C3)C=CC5=C4C(=O)C6=C(C5=O)OC7=CC(=C(C=C7C6=O)OC)OC)O)C(=O)N1CCO2 |
| InChI | InChI=1S/C29H21NO9/c1-29-11-13-8-12-4-5-14-21(19(12)25(33)20(13)28(35)30(29)6-7-38-29)26(34)22-23(31)15-9-17(36-2)18(37-3)10-16(15)39-27(22)24(14)32/h4-5,8-10,33H,6-7,11H2,1-3H3 |
| InChI Key | ORJRBJIJTSDUCG-UHFFFAOYSA-N |
Properties
| Appearance | Orange-red Powder |
| Antibiotic Activity Spectrum | Gram-positive bacteria; Yeast |
| Boiling Point | 806.2±65.0°C at 760 mmHg |
| Melting Point | >290°C (dec.) |
| Density | 1.6±0.1 g/cm3 |
| Solubility | Soluble in Chloroform, DMF, Methanol |
Reference Reading
1. The impact of LR-HSQMBC very long-range heteronuclear correlation data on computer-assisted structure elucidation
K A Blinov, A V Buevich, R T Williamson, G E Martin Org Biomol Chem. 2014 Dec 21;12(47):9505-9. doi: 10.1039/c4ob01418a. Epub 2014 Sep 30.
The impact of LR-HSQMBC very long-range (n)JCH heteronuclear shift correlation data as a supplement to HMBC data as input for the computer-assisted structure elucidation program, Structure Elucidator(®), is assessed for the first time. The severely proton-deficient xanthone antibiotic cervinomycin A2 and the alkaloid staurosporine were employed as a model compounds.
2. NMR Structure Elucidation of Small Organic Molecules and Natural Products: Choosing ADEQUATE vs HMBC
Alexei V Buevich, R Thomas Williamson, Gary E Martin J Nat Prod. 2014 Aug 22;77(8):1942-7. doi: 10.1021/np500445s.
Long-range heteronuclear shift correlation methods have served as the cornerstone of modern structure elucidation protocols for several decades. The (1)H-(13)C HMBC experiment provides a versatile and relatively sensitive means of establishing predominantly (3)J(CH) connectivity with the occasional (2)J(CH) or (4)J(CH) correlation being observed. The two-bond and four-bond outliers must be identified specifically to avoid spectral and/or structural misassignment. Despite the versatility and extensive applications of the HMBC experiment, it can still fail to elucidate structures of molecules that are highly proton-deficient, e.g., those that fall under the so-called "Crews rule". In such cases, recourse to the ADEQUATE experiments should be considered. Thus, a study was undertaken to facilitate better investigator understanding of situations where it might be beneficial to apply 1,1- or 1,n-ADEQUATE to proton-rich or proton-deficient molecules. Equipped with a better understanding of when a given experiment might be more likely to provide the necessary correlation data, investigators can make better decisions on when it might be advisible to employ one experiment over the other. Strychnine (1) and cervinomycin A2 (2) were employed as model compounds to represent proton-rich and proton-deficient classes of molecules, respectively. DFT methods were employed to calculate the relevant (n)J(CH) heteronuclear proton-carbon and (n)J(CC) homonuclear carbon-carbon coupling constants for this study.
3. LR-HSQMBC: a sensitive NMR technique to probe very long-range heteronuclear coupling pathways
R Thomas Williamson, Alexei V Buevich, Gary E Martin, Teodor Parella J Org Chem. 2014 May 2;79(9):3887-94. doi: 10.1021/jo500333u. Epub 2014 Apr 18.
HMBC is one of the most often used and vital NMR experiments for the structure elucidation of organic and inorganic molecules. We have developed a new, high sensitivity NMR pulse sequence that overcomes the typical (2,3)JCH limitation of HMBC by extending the visualization of long-range correlation data to 4-, 5-, and even 6-bond long-range (n)JCH heteronuclear couplings. This technique should prove to be an effective experiment to complement HMBC for probing the structure of proton-deficient molecules. The LR-HSQMBC NMR experiment can, in effect, extend the range of HMBC to provide data similar to that afforded by 1,n-ADEQUATE even in sample-limited situations. This is accomplished by optimizing responses for very small (n)JCH coupings as opposed to relying on the markedly less sensitive detection of long-range coupled (13)C-(13)C homonuclear pairs at natural abundance. DFT calculations were employed to determine whether the very long-range correlations observed for cervinomycin A2 were reasonable on the basis of the calculated long-range couplings.
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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 ╳
