Structure via PubChem · Public domain (PubChem)
gramicidin D
Sign in to saveAlso known as Gramicidin, Gramicidine, Gramicidin A, Gramicidin B, Gramicidin C, Bacillus brevis gramicidin D
Gramicidin, also called gramicidin D, is a mix of ionophoric antibiotics, gramicidin A, B and C, which make up about 80%, 5%, and 15% of the mix, respectively. Each has 2 isoforms, so the mix has 6 different types of gramicidin molecules. They can be extracted from Brevibacillus brevis soil bacteria. Gramicidins are linear peptides with 15 amino acids. This is in contrast to unrelated gramicidin S, which is a cyclic peptide.
Key facts
- Protein family.Symbol
- N/A
- Protein family.image
- Gramicidin A.gif
- Protein family.width
- 300
- Protein family.caption
- Gramicidin A head-to-head dimer
- Protein family.TCDB
- 1.D.1
- Protein family.OPM family
- 65
- Protein family.OPM protein
- 1grm
via Wikipedia infobox
Chemical data
- Formula
- C96H135N19O16
- Molecular weight
- 1811.2 g/mol
- IUPAC name
- (2R)-2-[[2-[[(2S)-2-formamido-3-methylbutanoyl]amino]acetyl]amino]-N-[(2S)-1-[[(2R)-1-[[(2S)-1-[[(2R)-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
- SMILES
- C[C@@H](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)[C@@H](CC(C)C)NC(=O)CNC(=O)[C@H](C(C)C)NC=O
- InChIKey
- NDAYQJDHGXTBJL-MWWSRJDJSA-N
- XLogP
- 10.9
- Polar surface area
- 520 Ų
- H-bond donors
- 20
- H-bond acceptors
- 16
- Formal charge
- 0
via PubChem
Research
4,349 papers- Gramicidin D conformation, dynamics and membrane ion transport.Biopolymers · 1999
- Gramicidin D enhances the antibacterial activity of fluoride.Bioorganic & medicinal chemistry letters · 2014
- In Silico and In Vitro Inhibition of SARS-CoV-2 PL(pro) with Gramicidin D.International journal of molecular sciences · 2023
- Gramicidin D and dithiothreitol effects on erythrocyte exovesiculation.Cell biochemistry and biophysics · 2005
- Gramicidin A in Asymmetric Lipid Membranes.Biomolecules · 2024
via PubMed
~4 min read
Encyclopedic overview
5 sectionsContents
- Medical uses
- History
- Structure and chemistry
- Pharmacological effect
- References
Gramicidin, also called gramicidin D, is a mix of ionophoric antibiotics, gramicidin A, B and C, which make up about 80%, 5%, and 15% of the mix, respectively. Each has 2 isoforms, so the mix has 6 different types of gramicidin molecules. They can be extracted from Brevibacillus brevis soil bacteria. Gramicidins are linear peptides with 15 amino acids. This is in contrast to unrelated gramicidin S, which is a cyclic peptide.
==Medical uses== Gramicidins work as antibiotics against gram-positive bacteria like Bacillus subtilis and Staphylococcus aureus, but not well against gram-negative ones like E. coli.
Excerpted from Wikipedia’s “gramicidin D” article, available under the CC BY-SA 4.0 licence.