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PF-1163B

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PF-1163B
Category Antibiotics
Catalog number BBF-03534
CAS 258871-60-2
Molecular Weight 461.63
Molecular Formula C27H43NO5
Purity ≥95%

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Capabilities & Facilities

Fermentation Lab

4 R&D and scale-up labs

2 Preparative purification labs

Fermentation Plant

Semi pilot, pilot and industrial plant 4 Manufacturing sites 7 Production lines at pilot scale 100+ Reactors of 30-4000 L; 170+ reactors of 20 KL-30 KL; 24+ reactors of >100 KL 2 Hydrogenation reactors (200 L, 4Mpa and 1000L, 4Mpa)

Product 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.

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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
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
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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