Gramicidin
[CAS# 1405-97-6]

Identification

• Classification: Biological >> Proteins and peptides
• Name: Gramicidin
• Synonyms: (2R)-2-[[(2S)-2-[[2-[[(2S)-2-formamido-3-methylbutanoyl]amino]acetyl]amino]propanoyl]amino]-N-[(2S)-1-[[(2R)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2R)-1-[[(2S)-1-[[(2R)-1-[[(2S)-1-[[(2R)-1-[[(2S)-1-(2-hydroxyethylamino)-3-(1H-indol-3-yl)-1-oxopropan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-3-(1H-indol-3-yl)-1-oxopropan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-3-(1H-indol-3-yl)-1-oxopropan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-3-(1H-indol-3-yl)-1-oxopropan-2-yl]amino]-3-methyl-1-oxobutan-2-yl]amino]-3-methyl-1-oxobutan-2-yl]amino]-3-methyl-1-oxobutan-2-yl]amino]-1-oxopropan-2-yl]-4-methylpentanamide
• Molecular Formula: C₉₉H₁₄₀N₂₀O₁₇
• Molecular Weight: 1882.29
• Protein Sequence: VGALAVVVWLWLWLWG
• CAS Registry Number: 1405-97-6
• EC Number: 215-790-4
• SMILES: C[C@@H](C(=O)N[C@H](CC(C)C)C(=O)N[C@@H](C)C(=O)N[C@H](C(C)C)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CC1=CNC2=CC=CC=C21)C(=O)N[C@H](CC(C)C)C(=O)N[C@@H](CC3=CNC4=CC=CC=C43)C(=O)N[C@H](CC(C)C)C(=O)N[C@@H](CC5=CNC6=CC=CC=C65)C(=O)N[C@H](CC(C)C)C(=O)N[C@@H](CC7=CNC8=CC=CC=C87)C(=O)NCCO)NC(=O)CNC(=O)[C@H](C(C)C)NC=O

Safety Data

• Hazard Symbols: GHS0i7 Warning
• Risk Statements: H302-H315-H319-H335
• Safety Statements: P261-P305+P351+P338

Discovery and Applications

Gramicidin is a cyclic peptide composed of alternating D- and L-amino acids, forming a ß-helical structure that enables its insertion into lipid membranes. The discovery of gramicidin dates back to 1939, when scientists at the Rockefeller Institute for Medical Research, including René Dubos and Selman Waksman, isolated it from a soil bacterium called Brevibacillus. The discovery marked the beginning of a new era in antibiotic research.

Gramicidin has a wide range of uses in medicine, especially in the treatment of local infections. It is often formulated into ointments, creams, and eye drops to treat bacterial infections of the skin, eyes, and mucous membranes. In addition to its antibacterial properties, gramicidin is also used in biotechnology and pharmaceutical research. Its ability to form ion channels in lipid membranes has been used to study membrane biophysics and drug delivery. Gramicidin-based model membranes are used in research laboratories to study drug-membrane interactions and develop novel drug delivery systems. In recent years, gramicidin has received attention in the fields of materials science and nanotechnology. Researchers explore its potential in the development of biomimetic membranes and nanoscale devices. Gramicidin channels embedded in lipid bilayers can serve as prototypes for designing synthetic ion channels and sensors with applications in drug screening, environmental monitoring, and biotechnology.

References

2000. Desformylgramicidin: A Model Channel with an Extremely High Water Permeability. Biophysical Journal. Sapar M. Saparov, Yuri N. Antonenko, Roger E. Koeppe, Peter Pohl.
DOI: 10.1016/s0006-3495(00)76493-9

2024. Antimicrobial Peptides in Reproductive Health and Therapeutic Applications. Evolution of Antimicrobial Peptides. Pradeep Nag B. Subramanyam, Sai Goutham Reddy Yeddula.
DOI: 10.1007/978-3-031-67515-7_13

2003. Structure-activity relationships of de novo designed cyclic antimicrobial peptides based on gramicidin S. Peptide Science. Darin L. Lee, Robert S. Hodges.
DOI: 10.1002/bip.10374