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Sparoxomycin A1

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Category Antibiotics
Catalog number BBF-02922
CAS 174390-01-3
Molecular Weight 377.44
Molecular Formula C13H19N3O6S2

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Fermentation Lab

4 R&D and scale-up labs

2 Preparative purification labs

Fermentation Plant

Semi pilot, pilot and industrial plant 4 Manufacturing sites 7 Production lines at pilot scale 100+ Reactors of 30-4000 L; 170+ reactors of 20 KL-30 KL; 24+ reactors of >100 KL 2 Hydrogenation reactors (200 L, 4Mpa and 1000L, 4Mpa)

Product 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.

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Synonyms 2-Propenamide, N-[(1S)-1-(hydroxymethyl)-2-[[S(R)]-[[[S(S)]-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)-[(S)-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-HCGIDLGCSA-N
Appearance Colorless Powder
Melting Point 169-173°C (dec.)
Solubility Soluble in Methanol
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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