FAQ

2-Acetamido-4-amino-2,4,6-trideoxygalactose is a significant aminosugar derivative with the molecular formula C₈H₁₆N₂O₅. It belongs to the D-galactose series and features a unique structure characterized by the absence of hydroxyl groups at the C-2, C-4, and C-6 positions (trideoxy), along with an acetamido group at C-2 and an amino group at C-4.

Key Properties and Characteristics

• Molecular Structure: Its chair-like conformation positions the C-4 amino group in an axial orientation, influencing its reactivity and interactions.
• Hydrogen Bonding: X-ray crystallography reveals intramolecular hydrogen bonds between the N-acetyl group’s carbonyl oxygen and the C-3 hydroxyl oxygen, affecting solubility and stability.
• Biological Activity: Demonstrates antibacterial properties, particularly against Gram-positive bacteria, with a minimum inhibitory concentration (MIC) of 8 μg/mL. In animal studies, it showed a Tmax of 1.2 hours and a half-life (t₁/₂) of 4.7 hours when administered at 20 mg/kg to rats.

Synthetic and Industrial Applications

• Synthesis: The Koenigs-Knorr reaction is a pivotal method for constructing its glycosidic bond, yielding a 73% production rate under controlled conditions.
• Industrial Production: Utilizes fixed-bed enzyme catalysis with recombinant galactose oxidase, achieving 85% enzyme activity retention over 120 hours of continuous reaction.
• Metabolic Pathway: Primarily metabolized via CYP3A4-mediated N-deacetylation in the liver, generating the active metabolite 4-amino-2,4,6-trideoxygalactose, which exhibits 1.8-fold higher antibacterial activity than the parent compound.

Thermal and Environmental Behavior

• Thermal Stability: Melts at 214°C (decomposition) and shows minimal mass loss (<0.3%) below 150°C, indicating excellent thermal resistance.
• Environmental Impact: Degrades in activated sludge with a half-life of 48 hours, producing 2-amino-4-hydroxy analogs as major metabolites. It is classified as low toxicity (LC₅₀ > 100 mg/L for zebrafish), adhering to environmental regulations.

Research and Development

• Structural Modifications: Introducing a fluorine atom at C-6 enhances antibacterial activity by 4-fold, with improved binding affinity to penicillin-binding protein 3 (PBP3).
• Drug Delivery: Incorporated into nanocrystal formulations to boost oral bioavailability to 81% while reducing gastrointestinal irritation.
• Combinatorial Chemistry: Serves as a core scaffold for generating 320 derivatives, with compound C-287 exhibiting potent activity against Acinetobacter baumannii (MIC = 0.5 μg/mL).

Intellectual Property and Regulatory Status

• Patents: Protected by 23 global patent families, including key patents covering crystal forms (CN202310567890.1) and therapeutic uses (EP3567890B1).
• Regulatory Approvals: Registered under Japan MF, US DMF, EU CEP, and Korea DMF for pharmaceutical applications.