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

1. 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.
2. 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.
3. 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.
4. Research on Antibiotic Resistance:
   • Tetracycline derivatives like this compound are studied for their 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:

1. https://www.benchchem.com/product/b1425360
2. https://cymitquimica.com/products/3D-MT04430/319426-63-6/tetracycline-10-o-b-d-galactopyranoside/
3. https://www.lgcstandards.com/MD/en/Tetracycline-10-O-b-D-Galactopyranoside/p/TRC-T291433?queryID=3af65b6ae966a6d17576a9820ed8a2a2
4. https://www.echemi.com/products/pd180521122284-tetracycline-10-o-b-d-galactopyranoside.html
5. https://www.sigmaaldrich.com/US/en/search/tetracycline?focus=products&page=1&perpage=30&sort=relevance&term=tetracycline&type=product_name
6. https://www.medchemexpress.com/tetracycline-10-o-d-galactopyranoside.html
7. https://pubchem.ncbi.nlm.nih.gov/compound/Tetracycline
8. https://www.scbt.com/es/p/tetracycline-10-o-b-d-galactopyranoside-319426-63-6