Blasticidin S Hydrochloride
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| Category | Antibiotics |
| Catalog number | BBF-04056 |
| CAS | 3513-03-9 |
| Molecular Weight | 458.90 |
| Molecular Formula | C17H26N8O5.HCl |
| Purity | ≥98% by HPLC |
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Description
Blasticidin S HCl is a nucleoside antibiotic that is first isolated from Streptomyces griseochromogenes. Blasticidin S inhibits protein synthesis in both prokaryotic and eukaryotic cells via suppressing peptide bond formation by the ribosome.
Specification
| Related CAS | 2079-00-7 (free base) |
| Synonyms | (S)-4-[[3-Amino-5-[(aminoiminomethyl)methylamino]-1-oxopentyl]amino]-1-(4-amino-2-oxo-1(2H)-pyrimidinyl)-1,2,3,4-tetradeoxy-β-D-erythro-hex-2-enopyranuronic acid hydrochloride; 4-Phenyl-3-propan-2-ylhept-1-en-5-yn-4-ol |
| Storage | Store at -20°C |
| IUPAC Name | (2S,3S,6R)-3-[[(3S)-3-amino-5-[carbamimidoyl(methyl)amino]pentanoyl]amino]-6-(4-amino-2-oxopyrimidin-1-yl)-3,6-dihydro-2H-pyran-2-carboxylic acid;hydrochloride |
| Canonical SMILES | CN(CCC(CC(=O)NC1C=CC(OC1C(=O)O)N2C=CC(=NC2=O)N)N)C(=N)N.Cl |
| InChI | InChI=1S/C17H26N8O5.ClH/c1-24(16(20)21)6-4-9(18)8-12(26)22-10-2-3-13(30-14(10)15(27)28)25-7-5-11(19)23-17(25)29;/h2-3,5,7,9-10,13-14H,4,6,8,18H2,1H3,(H3,20,21)(H,22,26)(H,27,28)(H2,19,23,29);1H/t9-,10-,13+,14-;/m0./s1 |
| InChI Key | YQXYQOXRCNEATG-NMQKUDMSSA-N |
| Source | Streptomyces griseochromogenes |
Properties
| Appearance | White to Off-white Solid |
| Application | Antibiotic that inhibits protein synthesis. |
| Boiling Point | 772.1°C at 760 mmHg |
| Melting Point | 210-250°C (dec.) |
| Solubility | Soluble in water, Acetic acid, Methanol |
Reference Reading
1.Crystal and molecular structure of the antibiotic blasticidin S hydrochloride pentahydrate.
Swaminathan V, Smith JL, Sundaralingam M, Coutsogeorgopoulos C, Kartha G. Biochim Biophys Acta. 1981 Oct 27;655(3):335-41.
The three-dimensional structure of blasticidin S hydrochloride pentahydrate, a member of the cytosine amino nucleoside antibiotics, has been solved using diffractometer data and refined to an R value of 0.115. The crystal data are a = 13.500(5), b = 20.387(7), c = 4.824 A, beta = 98.66(3) degrees, Z = 2, Dc = 1.389 g .cm-3, space group P21. The nucleoside base conformation is anti(chi = 86 degrees) and the 2',3'-unsaturated pyranosyl sugar exhibits a half-chair (degree H5) conformation. The amide plane is twisted from the trans position by about 10 degrees. The guanidium group and the amino group of the amino acid chain are positively charged, while the carboxyl group of the sugar is ionized. The chloride ion is surrounded by water molecules only, in a trigonal prismatic arrangement. The molecule has an extended conformation and there is an intramolecular hydrogen bond between the ammonium group and the carboxyl group. A striking feature of blasticidin is that all the hydrophilic groups lie on one side of the molecule and the hydrophobic groups on the other.
2.Induction of cholinergic differentiation with neurite sprouting by de novo biosynthesis and expression of GD3 and b-series gangliosides in Neuro2a cells.
Kojima N1, Kurosawa N, Nishi T, Hanai N, Tsuji S. J Biol Chem. 1994 Dec 2;269(48):30451-6.
The expression of a single glycosyltransferase, GD3 synthase, caused cholinergic differentiation with neurite sprouting. The cells that expressed GD3 were established from Neuro2a cells by transfection of a mammalian expression vector into which were carried a cDNA encoding GD3 synthase and the blasticidin-S-deaminase gene with a SV40 promoter, followed by selection with blasticidin-S-hydrochloride. The blasticidin-S-hydrochloride-resistant colonies derived from the cells transfected with the cDNA encoding GD3 synthase and the clonal cells (N2a-GD3) were spontaneously sprouting neurites but not those derived from cells transfected with only the vector without the cDNA encoding GD3 synthase (N2a-bsr). GD3 expression by N2a-GD3 was confirmed by immunostaining of the cells using the anti-GD3 monoclonal antibody, KM643. N2a-GD3 expressed not only GD3 but also GQ1b, one of the b-series gangliosides, whereas N2a-bsr did not express these gangliosides.
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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 ╳
