Nisamycin
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| Category | Antibiotics |
| Catalog number | BBF-02129 |
| CAS | 150829-93-9 |
| Molecular Weight | 425.47 |
| Molecular Formula | C24H27NO6 |
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Description
Nisamycin is originally isolated from Str. sp. K106. It has stronger anti-gram-positive bacteria and weaker anti-fungal and individual gram-negative bacteria activities. And it has weak cytotoxic effect. The IC50 of mouse leukemia P388 cells was 4.8 μg/mL.
Specification
| Synonyms | 2,4,6-Heptatrienoic acid, 7-(4-((5-cyclohexyl-1-oxo-2,4-pentadienyl)amino)-2-hydroxy-5-oxo-7-oxabicyclo(4.1.0)hept-3-en-2-yl)-, (1S-(1alpha,2beta,2(2E,4E,6E),4(2E,4E),6alpha))- |
| IUPAC Name | (2E,4E,6E)-7-[(1S,2R,6R)-4-[[(2E,4E)-5-cyclohexylpenta-2,4-dienoyl]amino]-2-hydroxy-5-oxo-7-oxabicyclo[4.1.0]hept-3-en-2-yl]hepta-2,4,6-trienoic acid |
| Canonical SMILES | C1CCC(CC1)C=CC=CC(=O)NC2=CC(C3C(C2=O)O3)(C=CC=CC=CC(=O)O)O |
| InChI | InChI=1S/C24H27NO6/c26-19(13-8-7-12-17-10-4-3-5-11-17)25-18-16-24(30,23-22(31-23)21(18)29)15-9-2-1-6-14-20(27)28/h1-2,6-9,12-17,22-23,30H,3-5,10-11H2,(H,25,26)(H,27,28)/b2-1+,12-7+,13-8+,14-6+,15-9+/t22-,23-,24+/m0/s1 |
| InChI Key | BUSGWUFLNHIBPT-XYBORKQMSA-N |
Properties
| Appearance | Pale Yellow Powder |
| Antibiotic Activity Spectrum | Gram-positive bacteria; Gram-negative bacteria; fungi; neoplastics (Tumor) |
| Boiling Point | 776.7±60.0°C at 760 mmHg |
| Melting Point | 122-124°C |
| Density | 1.3±0.1 g/cm3 |
Reference Reading
1. Nisamycin, a new manumycin group antibiotic from Streptomyces sp. K106. II. Structure determination and structure-activity relationships
K Hayashi, M Nakagawa, T Fujita, S Tanimori, M Nakayama J Antibiot (Tokyo). 1994 Oct;47(10):1110-5. doi: 10.7164/antibiotics.47.1110.
Nisamycin, a novel manumycin group antibiotic, was isolated from the culture broth of Streptomyces sp. K106. Structural elucidation of nisamycin was achieved by detailed NMR spectral analyses and comparison of the NMR data of nisamycin with those of other manumycin group antibiotics. The structure was confirmed by chromic acid oxidation. The absolute stereochemistry of nisamycin was determined to be 4R, 5S and 6R from the CD spectra of nisamycin and chromic oxidation of nisamycin. In addition, some structure activity-relationships were examined.
2. Total Synthesis of (±)-Nisamycin
Peter Wipf, Philip D G Coish J Org Chem. 1999 Jul 9;64(14):5053-5061. doi: 10.1021/jo990413m.
We have developed a highly convergent synthesis of the manumycin-type m-C7N-antibiotic nisamycin that is applicable to other members of this family of antibiotics. The synthesis features a three-step sequence to the epoxyquinol core that serves as a scaffold for the attachment of the polyene side chains. The eastern polyene side chain was constructed via a novel organozirconocene-mediated synthesis. Zirconocene methodology was also applied to the synthesis of the polyene side chains of asukamycin. The southern side chain of nisamycin was introduced via a Stille reaction that employed a vinyl bromo ketone, derived from an acid-sensitive bromo ketal. Pd-mediated coupling of the vinyl bromide with a stannyl TIPS ester gave TIPS-protected nisamycin that was readily converted to the natural product.
3. Nisamycin, a new manumycin group antibiotic from Streptomyces sp. K106. I. Taxonomy, fermentation, isolation, physico-chemical and biological properties
K Hayashi, M Nakagawa, M Nakayama J Antibiot (Tokyo). 1994 Oct;47(10):1104-9. doi: 10.7164/antibiotics.47.1104.
Nisamycin, a new manumycin group antibiotic, was isolated from the culture broth of Streptomyces sp. K106. This strain was designated to genus Streptomyces by the taxonomic features. Nisamycin was purified by ethyl acetate extraction, silica gel column chromatography, preparative silica gel TLC, and Sephadex LH-20 column chromatography as a pale yellow powder. Nisamycin is active against Gram-positive bacteria and fungi, and exhibits a cytotoxic activity.
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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 ╳
