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Elaiomycin

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Elaiomycin
Category Bioactive by-products
Catalog number BBF-01202
CAS 23315-05-1
Molecular Weight 258.36
Molecular Formula C13H26N2O3

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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

It is produced by the strain of Streptomyces hepaticus. It has the activity of anti-gram-positive bacteria and negative bacteria, especially has strong effect on mycobacterium tuberculosis. It is a carcinogen.

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Synonyms D-threo-4-Methoxy-3-(1-octenylazoxy)-2-butanol; D-threo-Methoxy-3-(1-octenyl-ONN-azoxy)-2-butanol; (2S,3S)-4-Methoxy-3-(1'-cis-octenyl-cis-azoxy)-2-butanol; 2-Butanol, 4-methoxy-3-(1-octenyl-ONN-azoxy)-, D-threo-; (E,Z)-(2S,3S)-4-Methoxy-3-(1-octenyl-ONN-azoxy)-2-butanol; 2-Butanol, 4-methoxy-3-(1-octenyl-ONN-azoxy)-, (E,Z)-(2S,3S)-
IUPAC Name [(2S,3S)-3-hydroxy-1-methoxybutan-2-yl]imino-[(Z)-oct-1-enyl]-oxidoazanium
Canonical SMILES CCCCCCC=C[N+](=NC(COC)C(C)O)[O-]
InChI InChI=1S/C13H26N2O3/c1-4-5-6-7-8-9-10-15(17)14-13(11-18-3)12(2)16/h9-10,12-13,16H,4-8,11H2,1-3H3/b10-9-,15-14?/t12-,13-/m0/s1
InChI Key BCPWSYQGYBTINM-ZABQTCLWSA-N
Appearance Yellow Oily Matter
Antibiotic Activity Spectrum Gram-positive bacteria; Gram-negative bacteria; Mycobacteria
Boiling Point 385.3 °C at 760 mmHg
Melting Point 105-110 °C (0.07 Pa)
Density 1.00 g/cm3
Solubility Freely soluble in general organic solvents; Slightly soluble in Water
1. Elaiomycins K and L, new azoxy antibiotics from Streptomyces sp. Tü 6399*
Niko Manderscheid, Soleiman E Helaly, Andreas Kulik, Jutta Wiese, Johannes F Imhoff, Hans-Peter Fiedler, Roderich D Süssmuth J Antibiot (Tokyo). 2013 Feb;66(2):85-8. doi: 10.1038/ja.2012.99. Epub 2012 Nov 14.
Elaiomycins K and L, two new azoxy-type antibiotics, were detected by HPLC-diode array screening in the culture filtrate extract of Streptomyces sp. Tü 6399. The structures were determined by high-resolution MS and 2-dimensional (1)H and (13)C correlated NMR spectroscopy including (15)N-NMR experiments and established these compounds as new members of the elaiomycin family. Both metabolites show a weak antibacterial activity against Bacillus subtilis and Staphylococcus lentus as well as against the phytophathogenic strain Xanthomonas campestris.
2. Elaiomycins B and C: alkylhydrazide antibiotics from Streptomyces sp. BK 190
Soleiman E Helaly, Alexander Pesic, Hans-Peter Fiedler, Roderich D Süssmuth Org Lett. 2011 Mar 4;13(5):1052-5. doi: 10.1021/ol1031014. Epub 2011 Feb 10.
Two novel alkyhydrazides, elaiomycins B and C, together with the azoxy antibiotic elaiomycin were isolated from Streptomyces sp. BK 190. The structures were established by 1D- and 2D-NMR spectroscopy including (15)N NMR studies and high-resolution orbitrap-ESI-mass spectrometry.
3. Elaiomycins D-F, antimicrobial and cytotoxic azoxides from Streptomyces sp. strain HKI0708
Ling Ding, Basile Le Sage Tchize Ndejouong, Armin Maier, Heinz-Herbert Fiebig, Christian Hertweck J Nat Prod. 2012 Oct 26;75(10):1729-34. doi: 10.1021/np300329m. Epub 2012 Sep 26.
Five new congeners of elaiomycin featuring the rare azoxy function were isolated from Streptomyces sp. strain HKI0708. Individual elaiomycins exhibit specific antimycobacterial, anti-Aspergillus, and cytotoxic activities, providing provisional data on structure-activity relationships. The co-occurrence of the azoxide variants indicates a biogenetic relationship that illustrates new diversification steps in elaiomycin biosynthesis.

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