Concanamycin C
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| Category | Antibiotics |
| Catalog number | BBF-01735 |
| CAS | 81552-34-3 |
| Molecular Weight | 823.06 |
| Molecular Formula | C45H74O13 |
| Purity | ≥98% |
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Description
It is produced by the strain of Streptomyces diastatochromogenes. It has antifungal, antiviral, immunosuppressive, cytotoxic and other activities, and is a specific inhibitor of V-type ATPase, which is an important tool for biochemical research.
Specification
| Synonyms | (3Z,5E,7R,8R,9S,10S,11R,13E,15E,17S,18R)-18-[(1S,2R,3S)-3-[(2R,4R,5S,6R)-4-[(2,6-Dideoxy-β-D-arabino-hexopyranosyl)oxy]tetrahydro-2-hydroxy-5-methyl-6-(1E)-1-propen-1-yl-2H-pyran-2-yl]-2-hydroxy-1-methylbutyl]-9-ethyl-8,10-dihydroxy-3,17-dimethoxy-5,7,11,13-tetramethyloxacyclooctadeca-3,5,13,15-tetraen-2-one; 4'-O-de(aminocarbonyl)-Concanamycin A |
| Storage | -20 °C |
| IUPAC Name | (3Z,5E,7R,8R,9S,10S,11R,13E,15E,17S,18R)-18-[(2S,3R,4S)-4-[(2R,4R,5S,6R)-4-[(2R,4R,5S,6R)-4,5-dihydroxy-6-methyloxan-2-yl]oxy-2-hydroxy-5-methyl-6-[(E)-prop-1-enyl]oxan-2-yl]-3-hydroxypentan-2-yl]-9-ethyl-8,10-dihydroxy-3,17-dimethoxy-5,7,11,13-tetramethyl-1-oxacyclooctadeca-3,5,13,15-tetraen-2-one |
| Canonical SMILES | CCC1C(C(CC(=CC=CC(C(OC(=O)C(=CC(=CC(C1O)C)C)OC)C(C)C(C(C)C2(CC(C(C(O2)C=CC)C)OC3CC(C(C(O3)C)O)O)O)O)OC)C)C)O |
| InChI | InChI=1S/C45H74O13/c1-13-16-34-28(7)37(56-38-22-33(46)42(50)31(10)55-38)23-45(52,58-34)30(9)41(49)29(8)43-35(53-11)18-15-17-24(3)19-26(5)39(47)32(14-2)40(48)27(6)20-25(4)21-36(54-12)44(51)57-43/h13,15-18,20-21,26-35,37-43,46-50,52H,14,19,22-23H2,1-12H3/b16-13+,18-15+,24-17+,25-20+,36-21-/t26-,27-,28-,29+,30+,31-,32+,33-,34-,35+,37-,38+,39+,40-,41-,42-,43-,45-/m1/s1 |
| InChI Key | XKYYLWWOGLVPOR-GKJVGUBMSA-N |
Properties
| Appearance | Crystal |
| Antibiotic Activity Spectrum | Fungi; Viruses |
| Boiling Point | 914.2 °C at 760 mmHg |
| Melting Point | 153-155 °C |
| Density | 1.18 g/cm3 |
| Solubility | Soluble in Isopropyl Alcohol, Methanol, Chloroform |
Reference Reading
1. Isolation and characterization of concanamycins A, B and C
H Kinashi, K Sakaguchi, K Someno J Antibiot (Tokyo) . 1984 Nov;37(11):1333-43. doi: 10.7164/antibiotics.37.1333.
Concanamycins A, B and C were isolated from the mycelium of Streptomyces diastatochromogenes S-45 as effective inhibitors of the proliferation of mouse splenic lymphocytes stimulated by concanavalin A. They represent a new class of 18-membered macrolide antibiotics, and are biologically active in vitro against several fungi and yeasts, but not against bacteria. Concanamycin A, the main component, has been identified with antifungal antibiotics, folimycin and A-661-I.
2. Inhibitory effect of modified bafilomycins and concanamycins on P- and V-type adenosinetriphosphatases
K Altendorf, E J Bowman, A Siebers, S Dröse, K U Bindseil, A Zeeck Biochemistry . 1993 Apr 20;32(15):3902-6. doi: 10.1021/bi00066a008.
Various ATPases have been tested for their sensitivity to naturally occurring unusual macrolides and their chemically modified derivatives, which are structurally related to bafilomycin A1 (1), the first specific inhibitor of vacuolar ATPases. The structure-activity study showed that in general the concanamycins, 18-membered macrolides, are better and more specific inhibitors than the bafilomycins of this class of membrane-bound ATPases. The additional carbohydrate residue is not responsible for the improved activity. The importance of an intact hemiketal ring, which is part of an intramolecular hydrogen-bonding network, and the effects of the size of the macrolactone ring are discussed. The structurally related elaiophylin (13), a C2-symmetric macrodiolide antibiotic, proved to be inactive on vacuolar ATPases but still retained its inhibitory effect on P-type ATPases.
3. Cellular role of the V-ATPase in Neurospora crassa: analysis of mutants resistant to concanamycin or lacking the catalytic subunit A
B J Bowman, E J Bowman J Exp Biol . 2000 Jan;203(Pt 1):97-106. doi: 10.1242/jeb.203.1.97.
Vacuolar ATPases (V-ATPases) are large complex enzymes that are structural and mechanistic relatives of F(1)F(o)-ATPases. They hydrolyze ATP and pump protons across membranes to hyperpolarize membranes and, often, to acidify cellular compartments. The proton gradients generated are used to drive the movement of various compounds across membranes. V-ATPases are found in membranes of archaebacteria and some eubacteria, in various components of the endomembrane system of all eukaryotes and in the plasma membranes of many specialized eukaryotic cells. They have been implicated in a wide variety of cellular processes and are associated with several diseases. Bafilomycin and concanamycin, specific inhibitors of V-ATPases, have been instrumental in implicating the V-ATPase in many of these roles. To understand further the mechanism of inhibition by these antibiotics and the physiological role of the enzyme in the cell, we have isolated mutants of the filamentous fungus Neurospora crassa that are resistant to concanamycin. Concanamycin has a dramatic effect on hyphal morphology at acid pH and is lethal at basic pH. In the resistant mutants, the cells can germinate and grow, although abnormally, in basic medium. Thus far, none of the mutants we have characterized is mutated in a gene encoding a subunit of the V-ATPase. Instead, the largest class of mutants is mutated in the gene encoding the plasma-membrane H(+)-ATPase. Mutations in at least four uncharacterized genes can also confer resistance. Inactivation of the V-ATPase by disruption of vma-1, which encodes the catalytic subunit (A) of the enzyme, causes a much more severe phenotype than inhibition by concanamycin. A strain lacking vma-1 is seriously impaired in rate of growth, differentiation and capacity to produce viable spores. It is also completely resistant to concanamycin, indicating that the inhibitory effects of concanamycin in vivo are due to inhibition of the V-ATPase. How the multiplicity of ATPases within a cell is regulated and how their activity is integrated with other metabolic reactions is poorly understood. Mutant analysis should help unravel this puzzle.
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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 ╳
