CAS 1404-64-4

(+)-Sparsomycin

Description:

(+)-Sparsomycin is an antibiotic compound that belongs to the class of aminoglycosides, primarily known for its role as an inhibitor of protein synthesis. It is derived from the bacterium Streptomyces griseus and exhibits a unique mechanism of action by binding to the ribosomal RNA, thereby interfering with the translation process in bacterial cells. This compound is characterized by its chiral nature, with the "(+)" designation indicating its specific optical activity. Sparsomycin has been studied for its potential therapeutic applications, particularly in the treatment of certain types of cancer and bacterial infections, although its clinical use is limited due to toxicity concerns. The substance is typically encountered in a solid form and is soluble in various organic solvents. Its chemical structure features a complex arrangement of rings and functional groups, contributing to its biological activity. Overall, (+)-Sparsomycin serves as an important compound in the field of medicinal chemistry and microbiology, providing insights into antibiotic mechanisms and potential therapeutic strategies.

Formula: C₁₃H₁₉N₃O₅S₂

InChI: InChI=1S/C13H19N3O5S2/c1-8-10(12(19)16-13(20)14-8)3-4-11(18)15-9(5-17)6-23(21)7-22-2/h3-4,9,17H,5-7H2,1-2H3,(H,15,18)(H2,14,16,19,20)/b4-3+/t9-,23+/m0/s1

InChI key: InChIKey=XKLZIVIOZDNKEQ-CLQLPEFOSA-N

SMILES: C(=C/C(N[C@H](CS(CSC)=O)CO)=O)\C1=C(C)NC(=O)NC1=O

Synonyms:

• (2E)-3-(2,4-dihydroxy-6-methylpyrimidin-5-yl)-N-[(2S)-1-hydroxy-3-{[(methylsulfanyl)methyl]sulfinyl}propan-2-yl]prop-2-enamide
• (2E)-N-[(1S)-1-(Hydroxymethyl)-2-[(R)-[(methylthio)methyl]sulfinyl]ethyl]-3-(1,2,3,4-tetrahydro-6-methyl-2,4-dioxo-5-pyrimidinyl)-2-propenamide
• (2E)-N-[(2S)-1-hydroxy-3-{[(methylsulfanyl)methyl]sulfinyl}propan-2-yl]-3-(6-methyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)prop-2-enamide
• (2E)-N-[2-hydroxy-1-({[(methylsulfanyl)methyl]sulfinyl}methyl)ethyl]-3-(6-methyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)prop-2-enamide
• 2-Propenamide, N-[(1S)-1-(hydroxymethyl)-2-[(R)-[(methylthio)methyl]sulfinyl]ethyl]-3-(1,2,3,4-tetrahydro-6-methyl-2,4-dioxo-5-pyrimidinyl)-, (2E)-
• 2-Propenamide, N-[1-(hydroxymethyl)-2-[[(methylthio)methyl]sulfinyl]ethyl]-3-(1,2,3,4-tetrahydro-6-methyl-2,4-dioxo-5-pyrimidinyl)-, [R-[R*,S*-(E)]]-
• 2-propenamide, 3-(2,4-dihydroxy-6-methyl-5-pyrimidinyl)-N-[(1S)-2-hydroxy-1-[[[(methylthio)methyl]sulfinyl]methyl]ethyl]-, (2E)-
• 5-Pyrimidineacrylamide, 1,2,3,4-tetrahydro-N-[1-(hydroxymethyl)-2-[[(methylthio)methyl]sulfinyl]ethyl]-6-methyl-2,4-dioxo-, (E)-(1S)-
• NSC 059729
• NSC 59729
• U 19183

Sparsomycin

CAS: 1404-64-4

Formula: C₁₃H₁₉N₃O₅S₂

Purity: 97%

Color and Shape: Solid

Molecular weight: 361.4371

Ref: IN-DA009GAE

Sparsomycin

CAS: 1404-64-4

Sparsomycin is an antitumor antibiotic. It also inhibits protein synthesis in the 70S and 80S ribosomal systems.

Formula: C₁₃H₁₉N₃O₅S₂

Purity: 98%

Color and Shape: Solid

Molecular weight: 361.44

Ref: TM-T24819

Sparsomycin

CAS: 1404-64-4

Formula: C₁₃H₁₉N₃O₅S

Molecular weight: 361.47

Ref: 4Z-S-074001

Sparsomycin

Controlled Product

CAS: 1404-64-4

Formula: C₁₃H₁₉N₃O₅S₂

Color and Shape: Neat

Molecular weight: 361.437

Ref: TR-S679270

Sparsomycin

CAS: 1404-64-4

Sparsomycin is an antibiotic compound, which is a secondary metabolite isolated from Streptomyces species. Its mode of action involves the inhibition of protein synthesis by targeting the large subunit of the ribosome, specifically binding to the 50S subunit in bacterial ribosomes and the 60S subunit in eukaryotic ribosomes. This binding interferes with peptide bond formation, thereby disrupting the translational process essential for protein synthesis.

Formula: C₁₃H₁₉N₃O₅S₂

Purity: Min. 95%

Molecular weight: 361.4 g/mol

Ref: 3D-BAA40464