| | BLASTICIDIN S Basic information |
| Product Name: | BLASTICIDIN S | | Synonyms: | 1(1’-Cytosinyl)-4-[L-3’-amino-5’(1’’-N-methylguanidino)valerlamino]1,2,3,4-te-tradeoxy-D-erythro-hex-2-enuronicacid;bab;Blas;Blaes;BLASTICIDIN S;.beta.-D-erythro-Hex-2-enopyranuronic acid, 4-3-amino-5-(aminoiminomethyl)methylamino-1-oxopentylamino-1-(4-amino-2-oxo-1(2H)-pyrimidinyl)-1,2,3,4-tetradeoxy-, (S)-;1(1'-Cytosinyl)-4-[L-3'-amino-5'(1''-N-methylguanidino)valerlamino]1,2,3,4-te-tradeoxy-D-erythro-hex-2-enuronic acid;bcs-3、bla-s | | CAS: | 2079-00-7 | | MF: | C17H26N8O5 | | MW: | 422.45 | | EINECS: | | | Product Categories: | FUNGICIDE | | Mol File: | 2079-00-7.mol |  |
| | BLASTICIDIN S Chemical Properties |
| Melting point | 235°C | | alpha | D11 +108.4° (water) | | Boiling point | 539.06°C (rough estimate) | | density | 1.1690 (rough estimate) | | vapor pressure | Low | | refractive index | 1.6910 (estimate) | | solubility | DMF: soluble; DMSO: soluble; Ethanol: soluble; Methanol: soluble; Water: soluble | | pka | 2.4 (carboxyl), 4.6,8.0 and>12.5 (three bases) | | Water Solubility | >30 g l-1(20 °C) | | form | A solid | | Stability: | Incompatible with strong oxidizing agents. | | EPA Substance Registry System | Blasticidin S (2079-00-7) |
| | BLASTICIDIN S Usage And Synthesis |
| Description | Nucleoside antibiotic produced by Streptomyces griseochromogenes
(1). Biosynthesized from cytosine, glucose, arginine,
and methionine (2). | | Uses | Blasticidin S is a nucleoside produced by several species of Streptomyces, first reported in the late 1950s. Blasticidin S is an antifungal agent with particularly potent activity against the rice pathogen, Piricularia oryzae, for which it was used commercially for some time in Japan. Blasticidin S inhibits protein synthesis and is active against bacteria, tumour cell lines and nematodes. More recently, blasticidin S has been used as a marker for strain manipulations. Blasticidin S provided by BioAustralis is presented as the free base to avoid problems associated with the use of the hydrochloride. | | Uses | Blasticidin-S is used for the control of rice blast (PyricuZuria oryzae)
by foliar application. | | Definition | ChEBI: A blasticidin that is an antibiotic obtained from Streptomyces griseochromogene. | | Production Methods | Blasticidin S is produced by Streptomyces griseochromogenes,
and has a wide range of antimicrobial activity (4).
This antibiotic was utilized in the Far East beginning in
1961 against the rice blast pathogen Pyricularia oryzae,
with effective control achieved at rates of 10–40 ppm (4). | | Pharmacology | Inhibits protein synthesis both in eukaryotes and in
prokaryotes (5,6). Interacts with ribosomal RNA in large
subunit, interfering with the transpeptidation step.
Inhibits cell-free protein synthesis in P. oryzae and
Escherichia coli. | | Metabolic pathway | Several blasticidin S-resistant microorganisms are
found to produce blasticidin S deaminase which
catalyzes the hydrolytic deamination of the cytosine
moiety in blasticidin S to give a non-toxic
deaminohydroxy derivative. | | Metabolism | 3H-blasticidin S administered to mice was excreted in
the urine and feces within 24 h. Cytomycin and cytosin
were identified as the main metabolites in and on rice
plants, respectively (7). In soil, DT50 < 5 d. Metabolized to
nontoxic deaminohydroxy blasticidin S by Aspergillus sp.
and resistant Bacillus cereus. Novel deaminase and coding
genes, BSD and bsr, were isolated as selectable marker
genes for genetic engineering (8). | | Toxicity evaluation | Acute oral LD50 for male rats: 56.8, female rats: 55.9,
male mice: 51.9, and female mice: 60.1 mg/kg. Acute
percutaneous LD50 for rats >500 mg/kg. Eye: severe irritation. | | Degradation | Blasticidin-S is obtained as white needle crystals which are very soluble in
water. The compound is stable in the pH range 5-7 but it is unstable under
alkaline conditions. It is readily degraded by sunlight when on the surface
of rice plants with the main degradation product being cytosine (2)
(Yamaguchi et al., 1972) as shown in Scheme 1. |
| | BLASTICIDIN S Preparation Products And Raw materials |
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