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Indanomycin

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Indanomycin
Category Antibiotics
Catalog number BBF-01902
CAS 66513-28-8
Molecular Weight 493.68
Molecular Formula C31H43NO4
Purity >95% by HPLC

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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

Indanomycin is an antibiotic of the pyrroloketoindane class produced by Streptomyces sp. It is an unusual pyrollic ionophore that is active against gram-positive bacteria and insects. It has antihypertensive properties. It is a growth promoter in ruminants.

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Synonyms X-14547A; X 14547A; 2H-Pyran-2-acetic acid, 6-(1-ethyl-4-(1-ethyl-2,3,3a,4,5,7a-hexahydro-4-(1H-pyrrol-2-ylcarbonyl)-1H-inden-5-yl)-1,3-butadienyl)tetrahydro-alpha, 5-dimethyl-, (1S-(1-alpha,3-alpha,beta,4-beta,5-beta(1E(2S*(S*),5R*,6S*),3E),7a-alpha))-; Antibiotic X-14547A
Storage Store at -20°C
IUPAC Name (2R)-2-[(2R,5S,6R)-6-[(3E,5E)-6-[(1S,3aR,4S,5S,7aS)-1-ethyl-4-(1H-pyrrole-2-carbonyl)-2,3,3a,4,5,7a-hexahydro-1H-inden-5-yl]hexa-3,5-dien-3-yl]-5-methyloxan-2-yl]propanoic acid
Canonical SMILES CCC1CCC2C1C=CC(C2C(=O)C3=CC=CN3)C=CC=C(CC)C4C(CCC(O4)C(C)C(=O)O)C
InChI InChI=1S/C31H43NO4/c1-5-21-13-16-25-24(21)15-14-23(28(25)29(33)26-11-8-18-32-26)10-7-9-22(6-2)30-19(3)12-17-27(36-30)20(4)31(34)35/h7-11,14-15,18-21,23-25,27-28,30,32H,5-6,12-13,16-17H2,1-4H3,(H,34,35)/b10-7+,22-9+/t19-,20+,21-,23+,24+,25+,27+,28+,30+/m0/s1
InChI Key BAIPOTOKPGDCHA-MWBHXQFBSA-N
Source Streptomyces sp.
Appearance Light Tan Solid
Antibiotic Activity Spectrum Gram-positive bacteria; parasites
Boiling Point 654°C at 760 mmHg
Melting Point 138-141°C
Density 1.115 g/cm3
Solubility Soluble in Ethanol, Methanol, DMF, DMSO
1. Indanomycin-related antibiotics from marine Streptomyces antibioticus PTZ0016
Xiao-Yuan Lian, Zhizhen Zhang Nat Prod Res . 2013;27(23):2161-7. doi: 10.1080/14786419.2013.793688.
Four indanomycin-related antibiotics 2-5 were isolated from the cultured broth of marine Streptomyces antibioticus strain PTZ0016. Their structures were characterised as 16-deethylindanomycin (2), iso-16-deethylindanomycin (3), 16-deethylindanomycin methyl ester (4) and iso-16-deethylindanomycin methyl ester (5) on the basis of NMR, HR-ESI-MS and CD evidences. Compounds 3-5 are new additions to the class of indanomycin antibiotics. All isolated compounds showed in vitro activity against Staphylococcus aureus with minimal inhibitory concentration at 4.0-8.0 μg/ml.
2. [Kafamycin--a new pyrrol ether antibiotic]
T N Drobysheva, M K Kudinova, T P Korobkova, N V Murenets, N A Kliuev Antibiot Med Biotekhnol . 1987 Nov;32(11):811-4.
Cafamycin is a novel polyether antibiotic active against gram-positive bacteria. It was isolated from the culture fluid of Streptomyces sp., an organism producing the anthracycline antibiotic galtamycin. The structure of cafamycin was assessed by spectral analysis: UV, PMR, mass spectroscopy and CD. Physico-chemical and biological properties of the antibiotic are described. Cafamycin was shown to be an analog of indanomycin (X-14547A), a pyrrol ether antibiotic.
3. Syntheses of the hexahydroindene cores of indanomycin and stawamycin by combinations of iridium-catalyzed asymmetric allylic alkylations and intramolecular Diels-Alder reactions
Günter Helmchen, Martin Gärtner, Gedu Satyanarayana, Sebastian Förster Chemistry . 2013 Jan 2;19(1):400-5. doi: 10.1002/chem.201202822.
Short and concise syntheses of the hexahydroindene cores of the antibiotics indanomycin (X-14547 A) and stawamycin are presented. Key methods used are an asymmetric iridium-catalyzed allylic alkylation, a modified Julia olefination, a Suzuki-Miyaura coupling, and an intramolecular Diels-Alder reaction.

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