Sparoxomycin A2
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| Category | Antibiotics |
| Catalog number | BBF-02923 |
| CAS | 174390-02-4 |
| Molecular Weight | 377.44 |
| Molecular Formula | C13H19N3O6S2 |
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Description
It is produced by the strain of Str. sparsogenes SN 2325. It is a novel mammalian cell proliferation effector that converts the transformed phenotype of Rous sarcoma virus-infected NRK cells to a normal phenotype. It has weak antimicrobial activity (such as Escherichia coli) but has no effect on staphylococcus aureus, candida albicans and staphylococcus grayi.
Specification
| Synonyms | 2-Propenamide, N-[(1S)-1-(hydroxymethyl)-2-[[S(R)]-[[[S(R)]-methylsulfinyl]methyl]sulfinyl]-ethyl]-3-(1,2,3,4-tetrahydro-6-methyl-2,4-dioxo-5-pyrimidinyl)-, (2E)- |
| IUPAC Name | (E)-N-[(2S)-1-hydroxy-3-[(R)-[(R)-methylsulfinyl]methylsulfinyl]propan-2-yl]-3-(6-methyl-2,4-dioxo-1H-pyrimidin-5-yl)prop-2-enamide |
| Canonical SMILES | CC1=C(C(=O)NC(=O)N1)C=CC(=O)NC(CO)CS(=O)CS(=O)C |
| InChI | InChI=1S/C13H19N3O6S2/c1-8-10(12(19)16-13(20)14-8)3-4-11(18)15-9(5-17)6-24(22)7-23(2)21/h3-4,9,17H,5-7H2,1-2H3,(H,15,18)(H2,14,16,19,20)/b4-3+/t9-,23+,24+/m0/s1 |
| InChI Key | ZIMCIWWBWLSQCN-VKTUOGNUSA-N |
Properties
| Appearance | Colorless Powder |
| Antibiotic Activity Spectrum | Gram-negative bacteria |
| Melting Point | 170-174°C (dec.) |
| Density | 1.559±0.06 g/cm3 (Predicted) |
| Solubility | Soluble in Methanol |
Reference Reading
1. Synthesis and morphological reversion activity on srctsNRK cells of pyrimidinylpropanamide antibiotics, sparsomycin, sparoxomycin A1, A2, and their analogues
N Nakajima, T Enomoto, N Matsuura, M Ubukata Bioorg Med Chem Lett. 1998 Dec 1;8(23):3331-4. doi: 10.1016/s0960-894x(98)00604-0.
Three pyrimidinylpropanamide antibiotics sparsomycin (1), sparoxomycins A1, A2 (2, 3), and also six analogues (4-9) have been synthesized by employing asymmetric sulfide oxidation conditions as a key step. Sparsomycin (1) and its alkyl analogues (5-7) showed higher morphological reversion activities on srctsNRK cells than 2 and 3.
2. Sparoxomycins A1 and A2, new inducers of the flat reversion of NRK cells transformed by temperature sensitive Rous sarcoma virus. II. Isolation, physico-chemical properties and structure elucidation
M Ubukata, T I Morita, M Uramoto, H Osada J Antibiot (Tokyo). 1996 Jan;49(1):65-70. doi: 10.7164/antibiotics.49.65.
Sparoxomycins A1 and A2, isolated from the fermentation broth and mycelium of Streptomyces sparsogenes SN2325, are new inducers of the flat reversion of NRK cells transformed by temperature sensitive Rous sarcoma virus. Sparoxomycins A1 and A2 were isolated by active carbon chromatography, centrifugal partition chromatography (CPC), ODS column chromatography and preparative HPLC. The structure of sparoxomycins were determined by spectroscopic evidences. Stereochemical assignments of these inducers were executed from the analyses of CD spectra.
3. Sparoxomycins A1 and A2, new inducers of the flat reversion of NRK cells transformed by temperature sensitive Rous sarcoma virus. I. Taxonomy of the producing organism, fermentation and biological activity
M Ubukata, T Morita, H Kakeya, K Kobinata, T Kudo, H Osada J Antibiot (Tokyo). 1996 Nov;49(11):1096-100. doi: 10.7164/antibiotics.49.1096.
Streptomyces sparsogenes SN-2325 isolated from a soil sample collected in Hokkaido, was found to produce sparoxomycins A1 and A2, new modulators of proliferation of mammalian cells. Sparoxomycins A1 and A2 reverse the morphology of temperature-sensitive mutant Rous sarcoma virus-infected NRK cells (src(ts)-NRK cells) from the transformed phenotype to the normal phenotype at the permissive temperature.
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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 ╳
