Gramicidin S or Gramicidin Soviet is an antibiotic that is effective against some gram-positive and gram-negative bacteria as well as some fungi.
CAT No: 10-101-248
CAS No:113-73-5
Synonyms/Alias:Gramicidin S;Gramicidin C;113-73-5;Gramicin S-A;Gramicin S 1;Gramicidina S;Gramicidin S [INN];Grammidin;Gramacidine S;Gramicidinum S;Gramacidine S [INN-French];Gramicidin s-a;Gramicidinum S [INN-Latin];Gramicidina S [INN-Spanish];Gramicidin s 1;gramicidine S;UNII-WHM29QA23F;WHM29QA23F;BRN 0605227;CHEBI:5530;Cyclo(L-valyl-L-ornithyl-L-leucyl-D-phenylalanyl-L-prolyl-L-valyl-L-ornithyl-L-leucyl-D-phenylalanyl-L-prolyl);DTXSID6046008;GRAMICIDIN S [MI];GRAMICIDIN S [MART.];GRAMICIDIN S [WHO-DD];(3R,6S,9S,12S,15S,21R,24S,27S,30S,33S)-9,27-bis(3-aminopropyl)-3,21-dibenzyl-6,24-bis(2-methylpropyl)-12,30-di(propan-2-yl)-1,4,7,10,13,19,22,25,28,31-decazatricyclo[31.3.0.015,19]hexatriacontane-2,5,8,11,14,20,23,26,29,32-decone;9062-61-7;DTXCID4026008;1,10-anhydro(L-leucyl-D-phenylalanyl-L-prolyl-L-valyl-L-ornithyl-L-leucyl-D-phenylalanyl-L-prolyl-L-valyl-L-ornithine);Gramacidine S (INN-French);Gramicidinum S (INN-Latin);GRAMICIDIN S (MART.);Gramicidina S (INN-Spanish);cyclo(L-leucyl-D-phenylalanyl-L-prolyl-L-valyl-L-ornithyl-L-leucyl-D-phenylalanyl-L-prolyl-L-valyl-L-ornithyl);gramicidin a s;NCGC00095992-01;Gramicidin S TFA salt;113-73-5?free base?;SCHEMBL135010;CHEMBL373496;HY-P5712;Tox21_111543;NCGC00095992-05;CAS-113-73-5;DA-63895;DA-73866;FG166334;CS-0889301;NS00011540;Q4147636;bis(3-aminopropyl)-dibenzyl-diisobutyl-diisopropyl-[?]decone;
Gramicidin S is a cyclic decapeptide antibiotic renowned for its distinctive amphipathic structure and potent membrane-disrupting properties. Isolated originally from Bacillus brevis, it features a highly stable cyclopeptide backbone and an alternating sequence of hydrophobic and basic amino acids, which confer both rigidity and affinity for lipid bilayers. Its ability to interact with and permeabilize biological membranes has made it a molecule of significant interest in biochemical research, particularly in studies probing membrane structure, peptide-membrane interactions, and antimicrobial mechanisms. Due to its physicochemical properties, Gramicidin S serves as a valuable tool in a variety of experimental and analytical contexts, supporting investigations across microbiology, biophysics, and peptide chemistry.
Membrane biophysics research: As a model antimicrobial peptide, Gramicidin S is widely employed to investigate the biophysical principles underlying peptide-lipid interactions. Its well-characterized mechanism of membrane disruption provides a basis for in vitro studies examining the effects of cyclic peptides on lipid bilayer integrity, membrane fluidity, and phase behavior. Researchers frequently utilize it to probe the dynamics of peptide-induced membrane permeabilization, helping to elucidate the structural determinants that govern peptide selectivity and potency against bacterial versus eukaryotic membranes.
Antimicrobial mechanism studies: The peptide's robust bactericidal activity, mediated by its capacity to destabilize and permeabilize prokaryotic cell membranes, has established it as a reference compound in mechanistic studies of antimicrobial action. Investigations often use Gramicidin S to benchmark the efficacy of novel antimicrobial agents or to dissect the sequence-activity relationships that influence peptide-driven lysis. Its broad-spectrum activity and resistance to proteolytic degradation make it a reliable control in comparative studies of peptide-based antimicrobial strategies.
Peptide-membrane interaction assays: The amphipathic nature of Gramicidin S allows its application in fluorescence spectroscopy, calorimetry, and other biophysical assays designed to measure peptide binding, insertion, and orientation within model membranes. These assays are instrumental in quantifying the thermodynamic and kinetic parameters of peptide-lipid association, supporting the rational design of membrane-active peptides with tailored properties. Its use in such assays aids in mapping the energetics of peptide-induced membrane perturbation and in validating computational models of peptide-membrane interactions.
Peptide synthesis and structural studies: Due to its unique cyclic structure and resistance to enzymatic degradation, Gramicidin S is frequently utilized as a reference scaffold in peptide synthesis research. Synthetic chemists and structural biologists study its conformational stability, backbone cyclization, and side chain orientation to inform the development of novel cyclic peptides with enhanced bioactivity or stability. Additionally, its structure serves as a template for the design of peptide analogs with modified pharmacological profiles or improved membrane selectivity.
Analytical method development: In analytical biochemistry, Gramicidin S is employed as a standard or probe in chromatographic and spectrometric techniques. Its defined molecular mass and robust chemical stability make it suitable for method validation in peptide quantification, purity assessment, and mass spectrometric calibration. Furthermore, its interaction with lipid vesicles and model membranes is leveraged in the development of analytical platforms for studying peptide-membrane dynamics, contributing to advances in both fundamental and applied biochemical research.
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