Ascamycin
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| Category | Antibiotics |
| Catalog number | BBF-00097 |
| CAS | 91432-48-3 |
| Molecular Weight | 451.84 |
| Molecular Formula | C13H18ClN7O7S |
| Purity | ≥95% |
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Description
Ascamycin is a 5'-O-sulfonamide ribonucleoside antibiotic produced by Streptomyces sp. JCM9888. The MIC values of Ascamycin against Xanthomonas citri, Xanthomonas oryzae and Mycobacterium phlei are 0.4 μg/mL, 12.5 μg/mL and 12.5 μg/mL, respectively.
Specification
| Synonyms | (+)-5'-O-[[(S)-2-Amino-1-oxopropyl]aminosulfonyl]-2-chloroadenosine; 2-Chloro-5'-O-[(L-alanylamino)sulfonyl]adenosine; 2-Chloro-5'-O-[[(S)-2-amino-1-oxopropyl]sulfamoyl]adenosine; 5'-O-{[(2S)-2-Amino-1-hydroxypropylidene]sulfamoyl}-2-chloroadenosine |
| Storage | Store at -20°C |
| IUPAC Name | [(2R,3S,4R,5R)-5-(6-amino-2-chloropurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl N-[(2S)-2-aminopropanoyl]sulfamate |
| Canonical SMILES | CC(C(=O)NS(=O)(=O)OCC1C(C(C(O1)N2C=NC3=C(N=C(N=C32)Cl)N)O)O)N |
| InChI | InChI=1S/C13H18ClN7O7S/c1-4(15)11(24)20-29(25,26)27-2-5-7(22)8(23)12(28-5)21-3-17-6-9(16)18-13(14)19-10(6)21/h3-5,7-8,12,22-23H,2,15H2,1H3,(H,20,24)(H2,16,18,19)/t4-,5+,7+,8+,12+/m0/s1 |
| InChI Key | LZMCAAGVMFMSKC-IZKXYQSCSA-N |
Properties
| Appearance | Needles |
| Antibiotic Activity Spectrum | Gram-negative bacteria; mycobacteria |
| Boiling Point | 738.8±70.0°C at 760 mmHg |
| Melting Point | >270°C (dec.) |
| Density | 2.1±0.1 g/cm3 |
| Solubility | Soluble in Ethanol, Water |
Reference Reading
1. Discovery and applications of nucleoside antibiotics beyond polyoxin
Hiroyuki Osada J Antibiot (Tokyo) . 2019 Dec;72(12):855-864. doi: 10.1038/s41429-019-0237-1.
Nucleoside antibiotics possess various biological activities such as antibacterial, antifungal, anticancer, and herbicidal activities. RIKEN scientists contributed to this area of research with two representative antifungal nucleoside antibiotics, blasticidin S and polyoxin. Blasticidin S was the first antibiotic exploited in agriculture worldwide. Meanwhile, the polyoxins discovered by Isono and Suzuki are still used globally as an agricultural antibiotic. In this review article, the research on nucleoside antibiotics mainly done by Isono and his collaborators is summarized from the discovery of polyoxin to subsequent investigations.
2. Mechanism of action and selective toxicity of ascamycin, a nucleoside antibiotic
K Isono, H Osada Antimicrob Agents Chemother . 1985 Feb;27(2):230-3. doi: 10.1128/AAC.27.2.230.
An unidentified Streptomyces sp. produces two nucleoside antibiotics, ascamycin and its dealanyl derivative. In contrast to the broad antibacterial activity of dealanylascamycin against various gram-negative and gram-positive bacteria, ascamycin showed selective toxicity against Xanthomonas citri and X. oryzae. Both ascamycin and dealanylascamycin inhibited the protein synthesis of X. citri, but only dealanylascamycin inhibited that of Escherichia coli. In cell-free systems from E. coli and X. citri, both antibiotics, at ca. 0.04 micrograms/ml, inhibited the polyuridylate-directed synthesis of polyphenylalanine by ca. 50%. These data suggest that ascamycin cannot permeate the bacterial membrane. The dealanylating activity toward ascamycin was found only on the cell surface of bacteria susceptible to ascamycin. Dealanylascamycin must then have been transported into cytoplasm, where it inhibited protein synthesis.
3. Purification and characterization of ascamycin-hydrolysing aminopeptidase from Xanthomonas citri
K Isono, H Osada Biochem J . 1986 Jan 15;233(2):459-63. doi: 10.1042/bj2330459.
A nucleoside antibiotic, ascamycin (9-beta-[5'-0-(N-L-alanyl) sulphamoyl-D-ribofuranosyl]-2-chloroadenine), has a selective antibacterial activity against Xanthomonas species. When ascamycin was dealanylated, dealanylascamycin showed a broad antibacterial activity against various Gram-negative and Gram-positive bacteria. Xanthomonas citri is susceptible to ascamycin by virtue of the ascamycin-dealanylating enzyme on the cell surface [Osada & Isono (1985) Antimicrob. Agents Chemother. 27, 230-233]. The enzyme (Xc aminopeptidase) was purified from X. citri cells by successive DEAE-cellulose, chromatofocusing and Sephadex G-100 column chromatography to a homogeneous state. The purified enzyme exhibited a single band with an Mr of 38 000 in SDS/polyacrylamide-gel electrophoresis. Gel filtration on a calibrated column indicated a similar Mr value. The isoelectric point of the enzyme was 5.7. The enzyme catalysed the hydrolysis of the alanyl group of ascamycin and liberated alanine from the sulphamoyl nucleoside. The enzyme also catalysed the hydrolysis of L-proline beta-naphthylamide and L-alanine beta-naphthylamide. The optimal pH and temperature for enzyme activity were pH 7.5-8.0 and 35-40 degrees C respectively. The enzyme was inhibited by thiol-enzyme inhibitors (i.e. rho-chloromercuribenzoate and N-ethylmaleimide), but was not affected by various naturally occurring aminopeptidase inhibitors (i.e. amastatin, bestatin, pepstatin and leupeptin). Mn2+ and Mg2+ activated the enzyme, whereas Cu2+, Zn2+ and Cd2+ were inhibitory.
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Bio Calculators
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Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
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Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
