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Takanawaene A

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Category Antibiotics
Catalog number BBF-03097
CAS 627509-56-2
Molecular Weight 536.70
Molecular Formula C30H48O8

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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

Takanawaene A is a pentaene macrolide antibiotic produced by Streptomyces sp. K99-5278. It inhibits the growth of Saccharomyces cerevisiae with IC50 of 21.8 µmol/L.

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Synonyms Fungicide K 99-5278A
IUPAC Name (17Z,19Z,21Z,23Z,25Z)-4,6,10,12,14,16-hexahydroxy-3,27,28-trimethyl-1-oxacyclooctacosa-17,19,21,23,25-pentaen-2-one
Canonical SMILES CC1C=CC=CC=CC=CC=CC(CC(CC(CC(CCCC(CC(C(C(=O)OC1C)C)O)O)O)O)O)O
InChI InChI=1S/C30H48O8/c1-21-13-10-8-6-4-5-7-9-11-14-24(31)17-27(34)19-28(35)18-25(32)15-12-16-26(33)20-29(36)22(2)30(37)38-23(21)3/h4-11,13-14,21-29,31-36H,12,15-20H2,1-3H3/b5-4-,8-6-,9-7-,13-10-,14-11-
InChI Key XZNYCRZDVXCORM-ATGFBPJCSA-N
Appearance Yellow Powder
Antibiotic Activity Spectrum yeast
Boiling Point 783.5±60.0°C at 760 mmHg
Melting Point 160°C
Density 1.1±0.1 g/cm3
Solubility Soluble in Methanol
1. Takanawaenes, novel antifungal antibiotics produced by Streptomyces sp. K99-5278. I. Taxonomy, fermentation, isolation and biological properties
Yong-Pil Kim, Hiroshi Tomoda, Kousuke Iizima, Takashi Fukuda, Atsuko Matsumoto, Yoko Takahashi, Satoshi Omura J Antibiot (Tokyo). 2003 May;56(5):448-53. doi: 10.7164/antibiotics.56.448.
Three new pentaene macrolides having a 28-membered ring, designated takanawaenes A, B and C, were isolated from the fermentation broth of Streptomyces sp. K99-5278 by solvent extraction, silica-gel column chromatography and HPLC. Takanawaenes showed antifungal activity against Aspergillus niger, Mucor racemosus, Candida albicans and Saccharomyces cerevisiae.
2. Takanawaenes, novel antifungal antibiotics produced by Streptomyces sp. K99-5278. II. Structure elucidation
Takashi Fukuda, Yong-Pil Kim, Kousuke Iizima, Hiroshi Tomoda, Satoshi Omura J Antibiot (Tokyo). 2003 May;56(5):454-8. doi: 10.7164/antibiotics.56.454.
The structures of takanawaenes A, B and C, novel antifungal antibiotics produced by Streptomyces sp. K99-5278, were elucidated by various spectroscopic analyses including UV and NMR, and spectrometric analyses including MS. They have the common skeleton of a 28-membered pentaene macrolide.

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