Tetracycline 10-O-b-D-galactopyranoside (CAS 319426-63-6)

Tetracycline 10-O-β-D-galactopyranoside, registered under the CAS number 319426-63-6, is a chemically modified derivative of tetracycline, where a galactopyranoside moiety is attached to the 10th carbon of the tetracycline core. This modification introduces a sugar component to the traditional tetracycline structure, which is known for its ability to bind to the 30S subunit of bacterial ribosomes and block the attachment of aminoacyl-tRNA to the mRNA-ribosome complex, thus inhibiting protein synthesis. The addition of the β-D-galactopyranoside group enhances the solubility and alters the physicochemical properties of the molecule, which can influence its interaction with biological membranes and molecular targets. In research contexts, Tetracycline 10-O-β-D-galactopyranoside has been utilized to investigate the impact of glycosylation on the pharmacokinetics and cellular uptake of tetracycline antibiotics. Studies involving this compound help in understanding how modifications in antibiotic structure affect their bioactivity and distribution within biological systems. Additionally, this glycosylated derivative serves as a tool in biochemical studies to explore the dynamics and mechanisms of antibiotic resistance, offering insights into how structural changes may overcome or circumvent established resistance pathways in microbial populations. This research is crucial for designing next-generation molecules to manage and prevent bacterial infections effectively.