Mutalomycin
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| Category | Antibiotics |
| Catalog number | BBF-01966 |
| CAS | 62618-08-0 |
| Molecular Weight | 754.98 |
| Molecular Formula | C41H70O12 |
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Description
Mutalomycin is a polyether antibiotic produced by Str. mutabilis NRRL 8088. It has anti-Gram-positive bacteria, anti-mycoplasma and anti-coccidial activity.
Specification
| Related CAS | 62696-99-5 (sodium salt) |
| Synonyms | antibiotic S 11743A |
| IUPAC Name | (2S)-2-[(2R,3R,4S,5R,6S)-2-hydroxy-6-[(1S)-1-[(2S,5R,7S,8R,9S)-7-hydroxy-2-[(2R,5S)-5-[(2R,3S,5R)-5-[(2S,3S,5R,6S)-6-hydroxy-3,5,6-trimethyloxan-2-yl]-3-methyloxolan-2-yl]-5-methyloxolan-2-yl]-2,8-dimethyl-1,10-dioxaspiro[4.5]decan-9-yl]ethyl]-4-methoxy-3,5-dimethyloxan-2-yl]propanoic acid |
| Canonical SMILES | CC1CC(C(OC1C2CC(C(O2)C3(CCC(O3)C4(CCC5(O4)CC(C(C(O5)C(C)C6C(C(C(C(O6)(C(C)C(=O)O)O)C)OC)C)C)O)C)C)C)(C)O)C |
| InChI | InChI=1S/C41H70O12/c1-20-17-22(3)39(11,45)50-31(20)29-18-21(2)35(48-29)38(10)14-13-30(49-38)37(9)15-16-40(53-37)19-28(42)23(4)32(51-40)24(5)33-25(6)34(47-12)26(7)41(46,52-33)27(8)36(43)44/h20-35,42,45-46H,13-19H2,1-12H3,(H,43,44)/t20-,21-,22+,23+,24+,25-,26+,27+,28-,29+,30+,31-,32-,33+,34-,35+,37-,38-,39-,40+,41+/m0/s1 |
| InChI Key | WWEDNBWYGGJQOV-RIWLGXEFSA-N |
Properties
| Appearance | Colorless Crystal |
| Antibiotic Activity Spectrum | Gram-positive bacteria; mycoplasma; parasites |
| Boiling Point | 814.8±65.0°C at 760 mmHg |
| Melting Point | 158-160°C |
| Density | 1.2±0.1 g/cm3 |
Reference Reading
1. Mutalomycin, a new polyether antibiotic taxonomy, fermentation, isolation and characterization
T Fehr, H D King, M Kuhn J Antibiot (Tokyo). 1977 Nov;30(11):903-7. doi: 10.7164/antibiotics.30.903.
Mutalomycin is a new metal-complexing polyether antibiotic produced by a strain of Streptomyces mutabilis NRRL 8088. The metabolite, a monocarboxylic acid, was isolated as the sodium salt C41H69NaO12. The structure of this polyether was established by X-ray analysis of its potassium salt C41H69KO12. Mutalomycin contains six heterocyclic rings and is structurally related to nigericin. The metabolite is active against gram-positive bacteria and Eimeria tenella (chicken coccidiosis).
2. 2-Epimutalomycin and 28-epimutalomycin, two new polyether antibiotics from Streptomyces mutabilis. Derivatization of mutalomycin and the structure elucidation of two minor metabolites
T Fehr, M Kuhn, H R Loosli, M Ponelle, J J Boelsterli, M D Walkinshaw J Antibiot (Tokyo). 1989 Jun;42(6):897-902. doi: 10.7164/antibiotics.42.897.
A number of derivatives of mutalomycin (1), a naturally occurring polyether antibiotic, have been synthesized. In the desulfurization reaction of the ethylthio derivative (5) of mutalomycin (1) with Raney-nickel we observed an unusual course of the reaction, namely the introduction of a hydroxy group instead of the usual exchange against hydrogen, leading to two reaction products, mutalomycin (1) and 28-epimutalomycin (3). The structure of 3 and 2-epimutalomycin (2), both minor metabolites from the mutalomycin fermentation, were elucidated by X-ray analysis.
3. Studies on the ionophorous antibiotics. XXVI. The assignments of the 13C-NMR spectra of lonomycin A and mutalomycin
H Seto, K Mizoue, N Otake J Antibiot (Tokyo). 1980 Sep;33(9):979-88. doi: 10.7164/antibiotics.33.979.
All resonances observed in the 13C-nmr spectra of the polyether antibiotics lonomycin A and mutalomycin have been assigned by the aid of biosynthetic method, selective proton decoupling as well as comparison with structurally related compounds.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
