PF-1163B
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| Category | Antibiotics |
| Catalog number | BBF-03534 |
| CAS | 258871-60-2 |
| Molecular Weight | 461.63 |
| Molecular Formula | C27H43NO5 |
| Purity | ≥95% |
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Description
PF-1163B is an antibiotic isolated from Penicillium species. It exhibits growth inhibitory activity against pathogenic fungal strain Candida albicans and inhibits the ergosterol biosynthesis in Candida albicans.
Specification
| Synonyms | Antibiotic PF-1163B; (-)-PF 1163B; 3S-[[4-(2-hydroxyethoxy)phenyl]methyl]-4,10R-dimethyl-13R-pentyl-1-oxa-4-azacyclotridecane-2,5-dione |
| Storage | Store at -20°C |
| IUPAC Name | (3S,10R,13R)-3-[[4-(2-hydroxyethoxy)phenyl]methyl]-4,10-dimethyl-13-pentyl-1-oxa-4-azacyclotridecane-2,5-dione |
| Canonical SMILES | CCCCCC1CCC(CCCCC(=O)N(C(C(=O)O1)CC2=CC=C(C=C2)OCCO)C)C |
| InChI | InChI=1S/C27H43NO5/c1-4-5-6-10-24-15-12-21(2)9-7-8-11-26(30)28(3)25(27(31)33-24)20-22-13-16-23(17-14-22)32-19-18-29/h13-14,16-17,21,24-25,29H,4-12,15,18-20H2,1-3H3/t21-,24-,25+/m1/s1 |
| InChI Key | PCRJJAXIHTZHNU-SDUSCBPUSA-N |
Properties
| Appearance | Oily Matter |
| Antibiotic Activity Spectrum | Fungi |
| Boiling Point | 649.9±50.0°C at 760 mmHg |
| Density | 1.0±0.1 g/cm3 |
| Solubility | Soluble in Methanol |
Reference Reading
1. Total synthesis and conformational analysis of the antifungal agent (-)-PF1163B
Jean-Pierre Gesson, Fodil Bouazza, Brigitte Renoux, Christian Bachmann Org Lett . 2003 Oct 30;5(22):4049-52. doi: 10.1021/ol035309c.
[reaction: see text]. (-)-PF1163B, a new macrocyclic antifungal antibiotic isolated from Streptomyces sp., has been prepared in eight steps from (S)-citronellene. The key step is a ring-closing metathesis reaction of an ester and amide derivative obtained from a substituted N-methyl-l-tyrosine.
2. PF1163A and B, new antifungal antibiotics produced by Penicillium sp. II. Physico-chemical properties and structure elucidation
T Usui, K Tatsuta, S Takano, T Watanabe, A Hosoya, T Sasaki, H Nose, M Kawaguchi, S Yoshida, Y Ohtsuka, T Shomura J Antibiot (Tokyo) . 2000 Jan;53(1):38-44. doi: 10.7164/antibiotics.53.38.
The structures of new antifungal antibiotics, PF1163A and B, were elucidated by spectroscopic analyses of the degradation products and by X-ray crystallography of the de-2-hydroxyethyl derivative of PF1163B. Both antibiotics consist of a 13-membered macrocyclic structure containing a derivative of N-methyl tyrosine and a hydroxy fatty acid. PF1163A differs from PF 1163B by having an additional hydroxyl group on the side chain.
3. PF1163A and B, new antifungal antibiotics produced by Penicillium sp. I. Taxonomy of producing strain, fermentation, isolation and biological activities
S Hoshiko, A Hosoya, A Seki, H Nose, T Sasaki, T Shomura, T Yaguchi J Antibiot (Tokyo) . 2000 Jan;53(1):33-7. doi: 10.7164/antibiotics.53.33.
Two novel antifungal antibiotics, PF1163A and B, were isolated from the fermentation broth of Penicillium sp. They were purified from the solid cultures of rice media using ethyl acetate extraction, silica gel and Sephadex LH-20 column chromatographies. PF1163A and B showed potent growth inhibitory activity against pathogenic fungal strain Candida albicans but did not show cytotoxic activity against mammalian cells. These compounds inhibited the ergosterol biosynthesis in Candida albicans.
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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 ╳
