CAS 82079-32-1

Thiolactomycin

Description:

Thiolactomycin is a naturally occurring antibiotic that belongs to the class of compounds known as thiolactones. It is characterized by its unique structure, which includes a thiolactone ring and a long aliphatic side chain. This compound exhibits potent antibacterial activity, particularly against Gram-positive bacteria, and has been studied for its potential use in treating various bacterial infections. Thiolactomycin functions by inhibiting the enzyme fatty acid synthase, which is crucial for bacterial lipid biosynthesis, thereby disrupting the bacterial cell membrane integrity. The compound is typically found in a solid state at room temperature and is soluble in organic solvents. Its chemical properties make it a subject of interest in medicinal chemistry and microbiology research. Additionally, due to its specific mechanism of action, thiolactomycin has been investigated for its potential role in overcoming antibiotic resistance in certain bacterial strains. However, further studies are necessary to fully understand its pharmacological profile and therapeutic applications.

Formula: C₁₁H₁₄O₂S

InChI: InChI=1S/C11H14O2S/c1-5-7(2)6-11(4)9(12)8(3)10(13)14-11/h5-6,12H,1H2,2-4H3/b7-6+/t11-/m1/s1

InChI key: InChIKey=SYQNUQSGEWNWKV-XUIVZRPNSA-N

SMILES: C(=C(/C=C)\C)\[C@]1(C)C(O)=C(C)C(=O)S1

Synonyms:

• (+)-Thiolactomycin
• (5R)-4-Hydroxy-3,5-dimethyl-5-[(1E)-2-methyl-1,3-butadien-1-yl]-2(5H)-thiophenone
• (R)-(+)-Thiolactomycin
• 2(5H)-Thiophenone, 4-hydroxy-3,5-dimethyl-5-(2-methyl-1,3-butadienyl)-, [R-(E)]-
• 2(5H)-Thiophenone, 4-hydroxy-3,5-dimethyl-5-[(1E)-2-methyl-1,3-butadien-1-yl]-, (5R)-
• 2(5H)-Thiophenone, 4-hydroxy-3,5-dimethyl-5-[(1E)-2-methyl-1,3-butadienyl]-, (5R)-
• 3(2H)-thiophenone, 5-hydroxy-2,4-dimethyl-2-[(1E)-2-methyl-1,3-butadien-1-yl]-, (2R)-
• Antibiotic 2-200

(R)-(+)-Thiolactomycin

Controlled Product

CAS: 82079-32-1

Applications (R)-(+)-Thiolactomycin is a natural product inhibitor of β-Ketoacyl-AcpM Synthase A (KasA). It inhibits the synthesis of mycolic acid which is a major cell wall component of Mycobacterium tuberculosis. Also an inhibitor of D-Aspartate oxidase (DDO).
References Kapilashrami, K., et al.: J. Biol. Chem., 288, 6045 (2013); Paneerselvam, V., et al.: J. Pharm. Res., 4, 4618 (2011); Katane, M., et al.: Biochimie, 92, 1371 (2010)

Formula: C₁₁H₁₄O₂S

Color and Shape: Off White To Light Beige

Molecular weight: 210.29

Ref: TR-T350880

(R)-(+)-Thiolactomycin-d3

Controlled Product

CAS: 82079-32-1

Formula: C₁₁D₃H₁₁O₂S

Color and Shape: Neat

Molecular weight: 213.311

Ref: TR-T350882

(R)-(+)-Thiolactomycin

CAS: 82079-32-1

(R)-(+)-Thiolactomycin is a potent inhibitor of protein interactions. It is also used as a research tool to study the structure and function of receptors and ion channels. (R)-(+)-Thiolactomycin has been shown to be an activator of Ligand-gated Ion Channels, which are transmembrane proteins that allow ions to flow across the membrane in response to the binding of a ligand. This drug binds to receptors on the surface of cells and blocks the flow of ions through these channels. This inhibits neurotransmitter release, resulting in therapeutic benefits for conditions such as epilepsy, schizophrenia, and pain management.

Formula: C₁₁H₁₄O₂S

Purity: Min. 95%

Molecular weight: 210.29 g/mol

Ref: 3D-HDA07932

Thiolactomycin

CAS: 82079-32-1

Thiolactomycin is a novel reversible dual inhibitor of D-amino acid oxidase (DAO) and D-Aspartate oxidase (DDO).

Formula: C₁₁H₁₄O₂S

Purity: 98%

Color and Shape: Solid

Molecular weight: 210.29

Ref: TM-T28964