Tetracycline 10-O-β-D-Galactopyranoside

Tetracycline 10-O-β-D-Galactopyranoside Tetracycline 10-O-β-D-galactopyranoside is a glycosylated derivative of tetracycline, a broad-spectrum antibiotic produced by the Streptomyces genus of Actinobacteria. This compound is notable for its antimicrobial properties and its role in protein synthesis inhibition, making it valuable in both therapeutic and research applications. Chemical Properties CAS Number : 319426-63-6 MDL No. : MFCD03453021 Catalog Number : A821062 EINECS : Not available Molecular Formula : C₂₈H₃₄N₂O₁₃ Molecular Weight : 606.58 g/mol Boiling Point : Not specified Melting Point : Not specified Flash Point : Not specified Density : Not specified Appearance : Not specified (typically a white to off-white powder) Storage Conditions : Store at 2–8 °C for long-term stability (months). Optical Rotation : Not specified Mechanism of Action Tetracycline 10-O-β-D-galactopyranoside exerts its antibacterial effects primarily through the inhibition of protein synthesis. It binds to the bacterial ribosome, specifically the 30S subunit, preventing the attachment of aminoacyl-tRNA to the ribosomal A site, which halts the addition of new amino acids to the growing peptide chain. Applications Antimicrobial Activity : Effective against a broad spectrum of bacteria, including both Gram-positive and Gram-negative organisms. It has demonstrated activity against resistant strains due to its unique structure that allows for enhanced uptake and efficacy. Molecular Biology Research : Utilized in gene expression studies, particularly in tetracycline-controlled transcriptional activation systems (Tet-On/Tet-Off). It serves as an effective inducer for regulating target gene expression in various experimental systems. Therapeutic Applications : Historically significant in treating infections caused by mycoplasmas, rickettsias, and chlamydiae. Its anti-inflammatory properties also make it useful in dermatological treatments for conditions such as acne and rosacea. Research on Antibiotic Resistance : Tetracycline 10-O-β-D-Galactopyranoside, a tetracycline derivative, is studied for its potential to overcome mechanisms of antibiotic resistance, providing insights into developing new therapeutic strategies. Preparation Methods The synthesis of Tetracycline 10-O-β-D-galactopyranoside typically involves the glycosylation of tetracycline with a galactose derivative, using glycosyltransferases or chemical catalysts under specific conditions to ensure selective formation of the glycosidic bond. Conclusion Tetracycline 10-O-β-D-galactopyranoside (CAS No. 319426-63-6) is a significant compound in both clinical and research settings due to its antimicrobial properties and role in protein synthesis inhibition. Its unique structure allows for targeted applications in treating bacterial infections and studying gene expression. Citations: https://www.benchchem.com/product/b1425360 https://cymitquimica.com/products/3D-MT04430/319426-63-6/tetracycline-10-o-b-d-galactopyranoside/ https://www.lgcstandards.com/MD/en/Tetracycline-10-O-b-D-Galactopyranoside/p/TRC-T291433?queryID=3af65b6ae966a6d17576a9820ed8a2a2 https://www.echemi.com/products/pd180521122284-tetracycline-10-o-b-d-galactopyranoside.html https://www.sigmaaldrich.com/US/en/search/tetracycline?focus=products&page=1&perpage=30&sort=relevance&term=tetracycline&type=product_name https://www.medchemexpress.com/tetracycline-10-o-d-galactopyranoside.html https://pubchem.ncbi.nlm.nih.gov/compound/Tetracycline https://www.scbt.com/es/p/tetracycline-10-o-b-d-galactopyranoside-319426-63-6