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Takanawaene C

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Category Antibiotics
Catalog number BBF-03099
CAS 627509-58-4
Molecular Weight 578.77
Molecular Formula C33H54O8

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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 C is a pentaene macrolide antibiotic produced by Streptomyces sp. K99-5278. It inhibits the growth of Saccharomyces cerevisiae with IC50 of 28.7 µmol/L.

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IUPAC Name (17Z,19Z,21Z,23Z,25Z)-4,6,10,12,14,16-hexahydroxy-3,15,27-trimethyl-28-propan-2-yl-1-oxacyclooctacosa-17,19,21,23,25-pentaen-2-one
Canonical SMILES CC1C=CC=CC=CC=CC=CC(C(C(CC(CC(CCCC(CC(C(C(=O)OC1C(C)C)C)O)O)O)O)O)C)O
InChI InChI=1S/C33H54O8/c1-22(2)32-23(3)15-12-10-8-6-7-9-11-13-18-29(37)24(4)30(38)21-28(36)19-26(34)16-14-17-27(35)20-31(39)25(5)33(40)41-32/h6-13,15,18,22-32,34-39H,14,16-17,19-21H2,1-5H3/b7-6-,10-8-,11-9-,15-12-,18-13-
InChI Key IAGPWEVRXPPSEQ-DISGBCGLSA-N
Appearance Yellow Powder
Antibiotic Activity Spectrum yeast
Melting Point 156°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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