Flavomycoin
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| Category | Antibiotics |
| Catalog number | BBF-00940 |
| CAS | 77814-07-4 |
| Molecular Weight | 738.94 |
| Molecular Formula | C40H66O12 |
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Description
Flavomycoin is a pentaene macrolide antibiotic produced by Streptomyces roseoflavus var. jenensis JA-5068. It has anti-yeast, microsporum, Trichophyton, Aspergillus niger and other fungal activity.
Specification
| Synonyms | Roflamycoin |
| IUPAC Name | (1R,3Z,5Z,7Z,9Z,11Z,15S,16S,19S,21S,23S,27R,29S,31R,33S,35S)-19,21,23,25,27,29,31,33,35-nonahydroxy-12,16-dimethyl-15-propan-2-yl-14,37-dioxabicyclo[31.3.1]heptatriaconta-3,5,7,9,11-pentaen-13-one |
| Canonical SMILES | CC1CCC(CC(CC(CC(CC(CC(CC(CC2(CC(CC(O2)CC=CC=CC=CC=CC=C(C(=O)OC1C(C)C)C)O)O)O)O)O)O)O)O)O |
| InChI | InChI=1S/C40H66O12/c1-26(2)38-27(3)15-16-29(41)17-30(42)18-31(43)19-32(44)20-33(45)21-34(46)22-35(47)24-40(50)25-36(48)23-37(52-40)14-12-10-8-6-5-7-9-11-13-28(4)39(49)51-38/h5-13,26-27,29-38,41-48,50H,14-25H2,1-4H3/b7-5-,8-6-,11-9-,12-10-,28-13-/t27-,29-,30-,31-,32?,33+,34-,35+,36-,37+,38-,40-/m0/s1 |
| InChI Key | HBOLDVSXCKYZJZ-QIHQEISASA-N |
Properties
| Appearance | Yellow-green Needle Crystal |
| Antibiotic Activity Spectrum | fungi; yeast |
| Melting Point | 161-163°C(dec.) |
| Solubility | Soluble in Pyridine, acetic acid, DMF |
Reference Reading
1. Streptomyces maghwi, a new species producing roflamycoin
M Afzal, N D Nimer, M Nazar Z Allg Mikrobiol. 1983;23(7):411-8. doi: 10.1002/jobm.3630230702.
A new Streptomyces species is described for which the name S. maghwi is proposed. The organism is characterized by a pink mass of aerial mycelium, spiral spore chains, spores with smooth surfaces and a nonchromogenic vegetative mycelium. S. maghwi produces roflamycoin (Schlegel et al. 1981) formerly known as flavomycoin (Schlegel et al. 1971). The type strain of S. maghwi is deposited with CBS, Netherland.
2. [Selectivity of the channels formed by flavomycoin in a lipid bilayer as a function of the concentrations of transported ions]
P A Grigor'ev, N I Markevich Biofizika. 1981 Nov-Dec;26(6):999-1003.
Experiments on selective properties of the flavomycoin channels in a lipid bilayer in the solution of KCl show that the permeability ratio PCl/PK decreased with KCl concentration. A mathematical model of ion transport is developed which provides a quantitative description of the observed nonmonotonic dependence of transmembrane potential at a zero current on the concentration of KCl. An increase in PK relative to PCl is due to the difference in location of the binding sites of K+ and Cl- in a channel. The binding sites of Cl- are closer to the channel mouth as compared with those of K+.
3. Roflamycoin--a new channel-forming antibiotic
P Grigorjev, R Schlegel, H Thrum, L Ermishkin Biochim Biophys Acta. 1985 Dec 5;821(2):297-304. doi: 10.1016/0005-2736(85)90099-9.
Ion permeability of lipid bilayers was studied in the presence of a new antifungal pentaene antibiotic, roflamycoin, the structure of which differs considerably from that of the well-known polyene channel-former amphotericin B. Both of them, however, show the property of increasing the membrane permeability only in the case of sterol-containing membrane when added on both its sides. The conductance is strongly dependent on the concentration of the antibiotic in the solutions and of sterol in the membrane. Unlike the amphotericin B channels, roflamycoin channels are potential-dependent and have short lifetime (approx. 1 s) and high conductance (approx. 100 ps in 1 M KCl), which increases linearly with the salt concentration and is not blocked by the familiar blockers of amphotericin B channels. The two antibiotics seem to have a common mechanism of channel formation, viz. the formation starts from two semi-pores assembled in the opposite monolayers from several molecules of the antibiotic and sterol. However, the inner diameter of the roflamycoin channel is larger because of the different antibiotic-to-sterol ratio in the channel aggregate. It is believed that the difference in the ratio is due to the presence of the methyl group in the polyene chain of roflamycoin, and the considerable difference in lifetimes of the two types of channels depends on the terminal groups of the antibiotics.
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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 ╳
