Cepafungin III
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| Category | Bioactive by-products |
| Catalog number | BBF-00213 |
| CAS | 130743-09-8 |
| Molecular Weight | 506.63 |
| Molecular Formula | C26H42N4O6 |
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Description
Cepafungin III is an acyl peptide antibiotic produced by Pseudomonas sp. CB-3. It has activity against Candida, Aspergillus fumigatus and Trichophyton, but it is not effective against Candida albicans M-9 infection in mice.
Specification
| Synonyms | 2,4-Decadienamide, N-(2-hydroxy-1-(((10-hydroxy-5-methyl-2,7-dioxo-1,6-diazacyclododec-3-en-8-yl)amino)carbonyl)propyl)-9-methyl-, (SS-(3E,5R*,8R*(1R*(2E,4E),2S*),10R*))- |
| IUPAC Name | (2E,4E)-N-[(2S,3R)-3-hydroxy-1-[[(3Z,5S,8S,10S)-10-hydroxy-5-methyl-2,7-dioxo-1,6-diazacyclododec-3-en-8-yl]amino]-1-oxobutan-2-yl]-9-methyldeca-2,4-dienamide |
| Canonical SMILES | CC1C=CC(=O)NCCC(CC(C(=O)N1)NC(=O)C(C(C)O)NC(=O)C=CC=CCCCC(C)C)O |
| InChI | InChI=1S/C26H42N4O6/c1-17(2)10-8-6-5-7-9-11-23(34)30-24(19(4)31)26(36)29-21-16-20(32)14-15-27-22(33)13-12-18(3)28-25(21)35/h5,7,9,11-13,17-21,24,31-32H,6,8,10,14-16H2,1-4H3,(H,27,33)(H,28,35)(H,29,36)(H,30,34)/b7-5+,11-9+,13-12-/t18-,19+,20-,21-,24-/m0/s1 |
| InChI Key | ZQOSECHKDTUIEK-NUIZVSKESA-N |
Properties
| Antibiotic Activity Spectrum | fungi |
| Boiling Point | 885.5°C at 760 mmHg |
| Melting Point | 215-220°C |
| Density | 1.17 g/cm3 |
Reference Reading
1. Isolation of cepafungins I, II and III from Pseudomonas species
J Shoji, H Hinoo, T Kato, T Hattori, K Hirooka, K Tawara, O Shiratori, Y Terui J Antibiot (Tokyo). 1990 Jul;43(7):783-7. doi: 10.7164/antibiotics.43.783.
New acylpeptide antibiotics named cepafungins I, II and III were isolated from the culture broth of a strain identified as Pseudomonas sp. These antibiotics are neutral substances, soluble in aqueous alcohols and dimethyl sulfoxide, and show UV maxima at 260.5 nm. The IR spectra indicated these to be peptides. Molecular formulas C28H46N4O6, C27H44N4O6 and C26H42N4O6 for cepafungins I, II and III were indicated by elemental analysis and SI-MS. Cepafungins exhibited inhibitory activity against yeast and fungi, and antitumor activity against P388 leukemia in mice.
2. Structures of cepafungins I, II and III
Y Terui, J Nishikawa, H Hinoo, T Kato, J Shoji J Antibiot (Tokyo). 1990 Jul;43(7):788-95. doi: 10.7164/antibiotics.43.788.
Structures of interesting acylpeptide antibiotics cepafungins I, II and III were elucidated by NMR spectroscopic studies and some degradation experiments. The antibiotics contain a common peptide part that consists of threonine and two unusual amino acid residues, gamma-hydroxylysine and 4-amino-2-pentenoic acid. The unusual amino acid residues compose an interesting 12-membered ring with an exocyclic N-terminus to which the threonine is connected. Different fatty acyl groups connected to the N-terminus of the threonine distinguish the three cepafungins. The major component I and minor component III are new substance, but the minor component II has a structure identical with that of the recently reported antibiotic glidobactin A.
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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 ╳
