Vancosamine

Vancosamine is a amino sugar that is a constituent of several antibiotics, including vancomycin, rhamnovancomycin, and avoparcin. It is a non-proteinogenic amino acid that is derived from glucose.

Structure and Properties

Vancosamine is a monosaccharide derivative, specifically an amino sugar. It is a stereoisomer of glucosamine, meaning it has the same molecular formula but a different three-dimensional arrangement of atoms. Vancosamine has a molecular formula of C_6H_13NO_5 and a molar mass of 179.17 g/mol.

The structure of vancosamine includes a hydroxyl group (-OH), an amino group (-NH2), and a carboxyl group (-COOH). The presence of these functional groups gives vancosamine its chemical properties, including its ability to form hydrogen bonds and its solubility in water.

Biological Role

Vancosamine is a component of several antibiotics, including vancomycin, rhamnovancomycin, and avoparcin. These antibiotics are used to treat a variety of bacterial infections, particularly those caused by Gram-positive bacteria. The presence of vancosamine in these antibiotics contributes to their antibacterial activity.

In the case of vancomycin, vancosamine is thought to interact with the peptidoglycan layer of bacterial cell walls, preventing the synthesis of new cell wall material and thus inhibiting bacterial growth. This makes vancomycin a valuable treatment for infections caused by methicillin-resistant Staphylococcus aureus (MRSA) and other drug-resistant bacteria.

Synthesis

Vancosamine is synthesized from glucose through a series of enzymatic reactions. The first step is the conversion of glucose to glucosamine by the enzyme glucosamine synthase. Glucosamine is then converted to vancosamine by the enzyme vancosamine synthase.

See Also

• Vancomycin
• Rhamnovancomycin
• Avoparcin
• Amino sugar
• Antibiotic