Gramicidin C , CAS No.3851247

CAS: 3851247 Cat. No.: G991325 Formula: C₆₀H₉₂N₁₂O₁₀ Peso molecolare: 1141.400

Storage

Room temperature

Specifications

Condizioni di conservazione di stoccaggio

Room temperature

Nomi e identificatori

Sorrisi canonici

CC(C)CC1C(=O)NC(C(=O)N2CCCC2C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)N3CCCC3C(=O)NC(C(=O)NC(C(=O)N1)CCCN)C(C)C)CC4=CC=CC=C4)CC(C)C)CCCN)C(C)C)CC5=CC=CC=C5

IUPAC Name

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

InChIKey

IUAYMJGZBVDSGL-UHFFFAOYSA-N

INCHI

1S/C60H92N12O10/c1-35(2)31-43-53(75)67-45(33-39-19-11-9-12-20-39)59(81)71-29-17-25-47(71)55(77)70-50(38(7)8)58(80)64-42(24-16-28-62)52(74)66-44(32-36(3)4)54(76)68-46(34-40-21-13-10-14-22-40)60(82)72-30-18-26-48(72)56(78)69-49(37(5)6)57(79)63-41(23-15-27-61)51(73)65-43/h9-14,19-22,35-38,41-50H,15-18,23-34,61-62H2,1-8H3,(H,63,79)(H,64,80)(H,65,73)(H,66,74)(H,67,75)(H,68,76)(H,69,78)(H,70,77)

Peso molecolare

1141.400

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic acids and derivatives
    • Classe Carboxylic acids and derivatives
      • Subclass Amino acids, peptides, and analogues
        • Level5 Peptides
          • Level6 Oligopeptides

• Kingdom: Organic compounds
• Superclass: Organic acids and derivatives
• Classe: Carboxylic acids and derivatives
• Subclass: Amino acids, peptides, and analogues
• Intermediate Tree Nodes: Peptides
• Direct Parent: Oligopeptides
• Alternative Parents: Cyclic peptides Macrolactams Alpha amino acids and derivatives Benzene and substituted derivatives Tertiary carboxylic acid amides Pyrrolidines Secondary carboxylic acid amides Lactams Azacyclic compounds Organic oxides Monoalkylamines Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Alpha-oligopeptide - Cyclic alpha peptide - Macrolactam - Alpha-amino acid or derivatives - Monocyclic benzene moiety - Benzenoid - Tertiary carboxylic acid amide - Pyrrolidine - Amino acid or derivatives - Carboxamide group - Lactam - Secondary carboxylic acid amide - Azacycle - Organoheterocyclic compound - Primary aliphatic amine - Primary amine - Amine - Organic nitrogen compound - Hydrocarbon derivative - Carbonyl group - Organic oxide - Organic oxygen compound - Organonitrogen compound - Organooxygen compound - Aromatic heteropolycyclic compound
• Descrizione: This compound belongs to the class of organic compounds known as oligopeptides. These are organic compounds containing a sequence of between three and ten alpha-amino acids joined by peptide bonds.
• External Descriptors: Not available

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Proprietà chimiche e fisiche

• Peso molecolare: 1141.400 g/mol
• XLogP3: 4.600
• Hydrogen Bond Donor Count: 10
• Hydrogen Bond Acceptor Count: 12
• Rotatable Bond Count: 16
• Exact Mass: 1140.71 Da
• Monoisotopic Mass: 1140.71 Da
• Topological Polar Surface Area: 325.000 Ų
• Heavy Atom Count: 82
• Formal Charge: 0
• Complexity: 2020.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 10
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

Application Protocols

No validated application protocols are provided in the Product Data for this item.

• Item-specific recommendations: Not specified for this item; refer to CoA/Spec Sheet and SDS.

General note: See the “Reaction Conditions” tab for literature-based guidance on preparing stock solutions and incorporating Gramicidin C into membrane systems. Users should optimize conditions for their specific instrumentation and assay format.

Biological Roles

General literature description (no clinical claims):

• Origin and function: Gramicidin isoforms (including Gramicidin C) are nonribosomal peptides from Bacillus species. Their biological role is defensive, disrupting target cell membranes by forming ion-conducting channels that collapse ion gradients.
• Channel properties: In lipid bilayers, Gramicidin C inserts as a β-helix monomer that dimerizes head-to-head across the membrane to form a narrow pore selective for monovalent cations (H+, Na+, K+, Cs+, Rb+). Divalent cations are generally excluded due to the pore size and dehydration penalty.
• Lipid dependence: Channel lifetime and conductance depend strongly on bilayer thickness, lipid composition (e.g., phosphatidylcholines vs. phosphatidylethanolamines), and temperature, making gramicidin channels sensitive probes of membrane physical properties.
• Biophysical utilities: Used to calibrate ion-sensitive fluorescent probes, assess membrane potential dissipation, and standardize single-channel electrophysiology measurements.
• Structure–activity: The sequence and tryptophan positions in Gramicidin C modulate dimer stability and channel kinetics relative to other isoforms (A/B), providing a platform to study sequence effects on membrane channel behavior.

Buffer Applications

Not a buffering reagent. Gramicidin C does not establish or maintain pH and is not used to prepare classical buffer systems.

Practical note (literature/general):

• It may be introduced into buffered media (HEPES, PBS, etc.) as a membrane-active ionophore to equilibrate monovalent cations or dissipate membrane potential in model membranes or cell-based assays. When doing so, maintain organic co-solvent content at the minimal level compatible with delivery and verify that the buffer composition (salts, serum proteins) does not sequester or inactivate the peptide.
• Filters and plastics can adsorb hydrophobic peptides; pre-rinse equipment with a small volume of working solution to improve delivery consistency.

Green Alternatives

Because Gramicidin C requires organic solvents for dissolution and membrane delivery, greener choices focus on selecting lower-toxicity, biodegradable, or lower-VOC options where compatible with the experiment.

• Greener solvent selection (literature/general):

  • Prefer ethanol (renewable, lower toxicity) over chlorinated solvents for stock preparation and bilayer deposition when solubility permits.
  • Use isopropanol as an alternative to methanol if higher toxicity of MeOH is a concern, balancing solubility tradeoffs.
  • Limit DMSO to the minimum feasible final concentration; though not particularly hazardous, it enhances dermal absorption of solutes—handle carefully.

• Process considerations:

  • Minimize solvent volumes and employ microvolumetric additions to membranes or liposomes.
  • Recover and segregate halogenated solvent waste when their use is unavoidable (e.g., chloroform for lipid film methods).

• Comparison (general, qualitative):

  • Ethanol: greener profile; good membrane compatibility; moderate solubilizing power.
  • Isopropanol: acceptable green solvent; slightly lower solubilizing power than ethanol for some peptides.
  • DMSO: effective solubilizer; not volatile; disposal is simpler than chlorinated solvents but consider downstream biological effects.
  • Chloroform/MeOH: strong solubilizers; poorer EHS and environmental profiles; reserve for specialized lipid film protocols.

Note: Solubility and performance should be verified empirically for your specific system.

Pharmaceutical Uses

No pharmacopoeial or excipient status is specified for this item; refer to CoA/Spec Sheet.

General/literature context (non-clinical):

• Gramicidin C is predominantly used as a research-grade ionophore in membrane biophysics and analytical assays. It is not typically employed as a formulation excipient.
• In process development or analytical settings, it can serve as a reference standard to validate ion flux assays or as a positive control in membrane potential measurements.

Note: This product is for research use only and is not intended for therapeutic, diagnostic, or clinical applications.

Physical Properties

• Appearance (Product Data): Not specified for this item; refer to CoA/Spec Sheet.
• Molecular Weight (Product Data): Not specified for this item; refer to CoA/Spec Sheet.
• Molecular Formula (Product Data): Not specified for this item; refer to CoA/Spec Sheet.

Literature/general properties for gramicidin family and Gramicidin C:

• Physical state: Hydrophobic peptide, typically an amorphous to microcrystalline solid (literature).
• Solubility: Poorly soluble/insoluble in water; soluble in methanol, ethanol, 2-propanol, chloroform, dichloromethane, DMF, and DMSO (literature). For biological work, concentrated stocks are often prepared in ethanol or DMSO, then diluted into aqueous buffers containing membranes/lipids.
• Melting behavior: Decomposes on heating; no sharp melting point (literature for peptide antibiotics).
• UV/Vis: Strong UV absorbance near 280 nm due to tryptophan residues; useful for quantitation by A280 using an empirically determined ε (literature; value depends on exact isoform and solvent).
• pKa/logP: Not typically defined for large peptides; practical behavior is extremely hydrophobic with strong membrane partitioning (literature).
• Stability: Stable as a dry solid protected from light and moisture; solution stability depends on solvent and temperature—organic stocks at low temperature are preferred for extended storage (literature guidance).

Quality and Grades

• Grade/Purity (Product Data): Not specified for this item; refer to CoA/Spec Sheet.

Interpretation and practical notes (general):

• In peptide commodities such as gramicidins, quality is often reported as peptide purity by HPLC (% area), identity by MS, and moisture/ash content. If a grade (e.g., “research grade,” “>95% HPLC”) is provided on the CoA, it typically denotes the chromatographic purity of the principal isoform and low levels of closely related congeners.
• Isoform composition: “Gramicidin C” refers to a specific sequence variant within the gramicidin family; analytical data (HPLC/HRMS) help confirm isoform enrichment and minimize A/B content. Review the CoA for isoform distribution if your application is sensitive to channel kinetics.
• UV considerations: If used in spectroscopy, low baseline impurities at 220–300 nm are desirable. HPLC-grade solvents and low-UV containers are recommended.
• Residual solvents/salts: For sensitive electrophysiology, confirm residual inorganic content and counterions (acetate, trifluoroacetate) if applicable.
• Recommendation: Verify the CoA for identity (MS), purity (HPLC), water content (Karl Fischer), and storage recommendations matching your intended use (e.g., planar bilayer vs. liposomes).

Reaction and Applications

This material is not typically used as a synthetic reagent; its value lies in membrane biophysics and ion-transport studies.

Key research applications (literature/general):

• Ionophore for monovalent cations: Forms head-to-head channel dimers in lipid bilayers; increases permeability to H+, Na+, K+, Cs+, Rb+ while excluding most divalent cations. Widely used to dissipate membrane potential or clamp ion gradients in model systems.
• Single-channel electrophysiology: Benchmark for planar bilayer recordings due to well-defined conductance states and characteristic lifetimes of channels.
• Liposome assays: Facilitates ion flux in reconstituted proteoliposomes to validate transport assays or calibrate ion-sensitive dyes/electrodes.
• Membrane biophysics: Probing bilayer thickness, elasticity, and lipid composition effects on channel kinetics.

Practical tips (literature):

• Prepare fresh stocks in ethanol or DMSO; protect from light. Adsorption to plastics can occur—use glass vials and glass syringes for accurate dosing.
• Incorporation: Add small aliquots to lipid bilayers or liposomes; allow sufficient time for partitioning into membranes before measurements.
• Concentration regime: Activities are typically observed at nanomolar to low micromolar concentrations in membrane systems (optimize per setup).

Note: The above are general literature practices and not item-specific specifications.

Reaction Conditions

Item-specific reaction conditions are not applicable; however, the following literature guidance addresses preparation and use in membrane systems.

• Stock solutions (literature): Dissolve Gramicidin C at 1–10 mg/mL in ethanol or DMSO. Vortex and sonicate briefly if needed. Protect from light. Use glass vials/syringes to minimize adsorption.
• Working concentrations (literature): For bilayer or liposome work, final concentrations are often in the nM–µM range, optimized per system to achieve measurable conductance or flux without nonspecific disruption.
• Incorporation methods (literature):
  • Planar bilayers: Add small aliquots to one side of the chamber under stirring; allow time for partitioning and dimer formation before recording.
  • Liposomes: Co-dissolve with lipids in chloroform/methanol, dry to a thin film, then rehydrate to encapsulate/partition; or post-insert by adding an ethanolic solution to preformed vesicles with gentle mixing.
• Temperature: Channel kinetics are temperature-dependent; maintain consistent thermal control during experiments.
• Compatibility: High ionic strength and certain detergents can alter activity; evaluate buffer composition empirically.

All values are general literature guidance, not item-specific specifications.

Safety and Handling

• GHS classification, signal word, H-statements, pictograms (Product Data): Not specified for this item; refer to SDS.
• Research use: For research use only (per Product Data). Not for human or animal consumption or clinical use.

General laboratory safety guidance (literature/standard practice for hydrophobic peptide ionophores):

• Hazards: May cause irritation to skin, eyes, and respiratory tract. Avoid creating and breathing dust/aerosols. Handle within fume hood or well-ventilated area.
• PPE: Laboratory coat, nitrile gloves, and safety glasses. For weighing fine powders, use dust control (weigh boats with covers, antistatic measures) and consider a particulate mask if dust generation cannot be avoided.
• Incompatibilities: Strong oxidizing agents may degrade peptides; avoid prolonged exposure to light and moisture. Avoid aqueous alkaline hydrolysis conditions.
• First aid overview: If inhaled, move to fresh air; seek medical attention if symptoms persist. In case of skin or eye contact, rinse with water for several minutes; remove contaminated clothing. If ingested, rinse mouth; do not induce vomiting; seek medical attention. Defer to the SDS for authoritative instructions.
• Spill/leak: Avoid dust formation, collect with damp disposable towels or HEPA vacuum, place in suitable container for disposal according to institutional and local regulations.
• Waste: Dispose of peptide-containing organic solutions as hazardous chemical waste following local regulations.

Solvent Selection

Gramicidin C is highly hydrophobic and water-insoluble; solvent choice is critical for preparing concentrated, clear stock solutions without aggregation.

• Polarity/miscibility profile (literature):

  • Soluble: Ethanol, methanol, 2-propanol, n-propanol, DMSO, DMF, chloroform, dichloromethane.
  • Practically insoluble: Water and aqueous buffers without co-solvent.

• Typical use scenarios:

  • Prepare 1–10 mg/mL stocks in ethanol or DMSO (literature), then dilute into aqueous media containing liposomes or membranes. Keep final organic content as low as compatible with the biological system (often ≤0.1–1% v/v, literature guidance).
  • For planar lipid bilayers, deposition from volatile solvents (ethanol, hexane/ethanol mixtures, or chloroform/methanol) onto membranes is common (literature).

• Selection tips:

  • Choose ethanol when downstream compatibility with cells or bilayers demands lower solvent toxicity and easy evaporation.
  • Use DMSO for maximum solubilizing power and minimal volatility; filter sterilize if needed through low-protein-binding membranes.
  • Avoid prolonged exposure in strong acids/bases during dissolution to prevent peptide hydrolysis.

• Comparison (general):

  • Ethanol: greener, volatile, mild; limited solubility vs. DMSO.
  • DMSO: excellent solubilizer; non-volatile; higher residual in final system.
  • Chloroform/MeOH: powerful for lipid film methodologies; higher health and environmental burden.

Storage and Reconstitution

• Storage conditions (Product Data): Room temperature.
• Shipped in (Product Data): Not specified for this item; refer to CoA/Spec Sheet.

General/literature guidance:

• Solid storage: Keep tightly closed in a desiccated, light-protected container. While room temperature storage is listed, many users store hydrophobic peptides at 2–8 °C or lower for extended periods to minimize degradation. Avoid repeated warming/cooling in humid air.
• Reconstitution: Prepare concentrated stocks in ethanol or DMSO. Mix gently to avoid foaming; brief sonication can aid dissolution. Filter through low-protein-binding membranes if particulate matter is observed.
• Aliquoting: Dispense single-use aliquots to avoid repeated freeze–thaw of solutions. Store solutions at ≤−20 °C for longer-term use when compatible with solvent and container.
• Containers: Prefer glass vials and syringes to limit adsorption; if plastics are used, pre-rinse with working solution and verify recovery.
• Stability checks: Monitor by HPLC/UV for potency over time; discard if significant degradation or precipitation is detected.

Always consult the product’s CoA/Spec Sheet and SDS for definitive item-specific instructions.

Structure and Identity

Brief overview: Gramicidin C is a hydrophobic, linear pentadecapeptide (15-mer) belonging to the gramicidin family produced by Bacillus species. It is typically obtained as a defined component within the gramicidin mixture (A/B/C isoforms) and is used as a monovalent-cation ionophore in membrane biophysics.

• Item-specific identifiers (Product Data):

  • SKU: G991325
  • Product Name: Gramicidin C
  • CAS: 3851247
  • CID: 3851247
  • InChIKey: 150549 (as provided)
  • SMILES: Not specified for this item; refer to CoA/Spec Sheet.

• Molecular formula and MW (Product Data): Not specified for this item; refer to CoA/Spec Sheet.

• Structural features (general/literature):

  • Linear peptide of 15 amino acids with alternating L/D configurations; highly enriched in hydrophobic residues (Val, Leu/Ile, Trp).
  • N-terminus typically formylated; C-terminus often ethanolamide (literature, gramicidin family characteristic).
  • Adopts a head-to-head β6.3 helical dimer within lipid bilayers to form ion-conducting channels selective for monovalent cations.

• 2D structure description (general):

  • A linear sequence of amide linkages (peptide bonds) connecting hydrophobic side chains; indole rings from tryptophans are distributed along the backbone; terminal formyl group at N-terminus and an amide/ethanolamide functionality at the C-terminus (literature, gramicidin family).

Synthetic Utility

This compound is not commonly used as a reagent or building block in synthetic chemistry.

Potential roles (general/literature):

• Reference material: A well-characterized ion-channel forming peptide for benchmarking electrophysiological setups or validating liposome-based transport assays.
• Analytical calibrant: Due to strong absorbance near 280 nm (Trp residues), can serve as a qualitative standard for peptide detection/quantitation methods after appropriate calibration.
• Peptide chemistry studies: A model system to study sequence–structure–function in membrane-active peptides; may be used to test purification, formulation, and delivery methods for hydrophobic peptides.

For classical synthetic transformations (e.g., cross-couplings, condensations), Gramicidin C has no typical application; users seeking reagents for synthesis should consult other product categories (coupling reagents, catalysts, solvents).

Target Specificity

This section applies to immuno/biologic reagents (e.g., antibodies, ligands). No target specificity information is provided for this item and it is not an antibody or affinity reagent.

• Item-specific data: Not specified for this item; refer to CoA/Spec Sheet.