Syringomycin

Syringomycin is a cyclic lipodepsipeptide antibiotic produced by certain strains of the bacteria Pseudomonas syringae. It is part of a larger group of similar compounds known as the syringomycins, which are known for their ability to form ion channels in lipid bilayers.

Structure and Synthesis

Syringomycin is a cyclic lipodepsipeptide, meaning it is composed of a peptide ring and a lipid tail. The peptide ring contains several unusual amino acids, including the rare D-isoleucine and D-allo-isoleucine. The lipid tail is a 3-hydroxy fatty acid.

The synthesis of syringomycin is carried out by a nonribosomal peptide synthetase (NRPS) in P. syringae. This NRPS is a large, multi-domain enzyme that assembles the syringomycin molecule one piece at a time, in a manner similar to a factory assembly line.

Mechanism of Action

Syringomycin works by inserting itself into the cell membrane of a target organism, where it forms a pore or ion channel. This disrupts the normal functioning of the membrane, leading to cell death. The ability of syringomycin to form ion channels is thought to be due to its cyclic lipodepsipeptide structure.

Uses

Due to its antibiotic properties, syringomycin has potential uses in medicine and agriculture. However, its use is currently limited due to its toxicity to mammals and plants. Research is ongoing to modify syringomycin or find related compounds with less toxicity.

See Also

• Pseudomonas syringae
• Nonribosomal peptide
• Antibiotic resistance