L-DPPG-d , CAS No.L1442148

CAS: L1442148 Cat. No.: L1442148 Fórmula: C₃₈H₆₆D₉O₁₀P Peso molecular: 732.03

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Visão geral

L-DPPG-d 9 is deuterium labeled L-DPPG.

Specifications

Condições de armazenamento de armazenamento

Store at -20°C

Enviado em

Ice chest + Ice pads

Este produto requer transporte de cadeia fria. Serviços terrestres e outros serviços econômicos não estão disponíveis.

Nomes e identificadores

• Peso molecular: 732.03

Application Protocols

General laboratory protocol examples for L‑DPPG‑d (literature/practice). Adjust parameters to your setup and verify with small‑scale pilots.

• Large unilamellar vesicles (LUVs) by extrusion:

  1. Dissolve lipid at 10–20 mg/mL in CHCl3:MeOH (2:1). Deposit in a round‑bottom flask and rotary‑evaporate to a thin film; desiccate ≥1 h.
  2. Hydrate with 10–25 mM HEPES, 150 mM NaCl, pH 7.4 pre‑heated to 55–60 °C. Final lipid 1–10 mM.
  3. Vortex, then perform 10–15 freeze–thaw cycles between liquid N2 and 60 °C water bath.
  4. Extrude through 200 nm then 100 nm membranes at 55–60 °C (10–21 passes). Validate by DLS and zeta potential.

• Small unilamellar vesicles (SUVs) by sonication:

  1. Prepare MLVs as above. 2) Bath or probe sonicate at 55–60 °C until clear; keep sample under inert gas; avoid overheating.

• Supported lipid bilayers (SLBs):

  • Form LUVs (50–100 nm), then incubate on plasma‑cleaned silica at 37–50 °C with 2–5 mM Ca2+ to promote vesicle fusion. Rinse to remove excess vesicles; confirm by FRAP.

• Deuterated sample considerations:

  • Use deuterated solvents/buffers (as required), avoid protiated contaminations, and record D2O fraction and temperature for SANS/2H NMR reproducibility.

These are illustrative, research‑use procedures; optimize for composition, cargo, and instrumentation.

Biological Roles

Phosphatidylglycerol (PG) is a ubiquitous anionic phospholipid in bacteria, plants, and mitochondria. DPPG is a saturated PG analogue used to model PG behavior with well‑defined acyl chains; deuteration enables high‑contrast biophysical interrogation.

• Membrane architecture (literature):
  • Contributes negative surface charge, influencing electrostatic interactions with ions, peripheral proteins (e.g., C2, annexins), and cationic peptides.
  • Precursor relationship: PG is the biosynthetic precursor to cardiolipin in bacteria and mitochondria, linking PG abundance to respiratory membrane function.
• Biophysical properties:
  • High gel–fluid transition (≈41–45 °C) provides a rigid lamellar gel at ambient temperature, transitioning to a fluid Lα phase upon heating. This makes DPPG a benchmark for phase behavior studies.
  • Promotes domain formation when mixed with zwitterionic lipids (e.g., DPPC), modulating raft‑like behavior and lateral organization via charge and hydrogen bonding.
• Interactions with biomolecules:
  • Strongly binds divalent cations (Ca2+, Mg2+), which can bridge headgroups, condense membranes, and alter curvature stress.
  • Serves as a platform to study pore formation and selectivity of antimicrobial peptides and membrane‑active toxins.
• Analytical leverage of deuteration:
  • 2H NMR provides segmental order parameters along deuterated chains; SANS/NR contrast distinguishes leaflets and protein vs. lipid scattering.

Note: These are general biological roles of PG lipids and research uses of deuterated analogs; no clinical or diagnostic claims are made.

Buffer Applications

This product is not a buffering reagent. However, buffer composition is critical for preparing and studying L‑DPPG‑d membranes.

• Typical hydration buffers (practical guidance):
  • HEPES or Tris, 10–25 mM, pH 7.2–7.5, with 100–150 mM NaCl to screen electrostatic repulsion among anionic headgroups.
  • For divalent cation studies, add 0.5–5 mM CaCl2 or MgCl2, noting effects on vesicle stability and fusion.
  • For neutron/NMR applications, prepare buffers in D2O or mixed H2O/D2O to control contrast; match ionic strength to protiated buffers.
• Hydration conditions:
  • Heat buffer to 50–60 °C (above DPPG Tm) during hydration and extrusion/sonication to ensure fluidity.
  • Avoid high pH (>8.5) to minimize ester hydrolysis; avoid strong oxidizers.
• Additives:
  • 5–10 mol% cholesterol can modulate permeability; 0.1–1 mol% fluorescent probes (e.g., NBD‑PE) for imaging; ensure deuteration strategy if contrast is critical.
• Storage of buffers:
  • Filter (0.22 µm), degas if doing scattering experiments, and equilibrate temperature to measurement conditions.

Formulation specifics (salt, pH, and cation content) should be optimized for the intended membrane assay; verify compatibility with your cargo and analytical method.

Green Alternatives

While chloroform/methanol systems are traditional for phospholipid handling, greener workflows can reduce halogenated solvent use and improve lab safety without compromising performance.

• Greener handling options (literature/practice):

  • Ethanol or isopropanol stocks: dissolve L‑DPPG‑d warm (≥45–50 °C), then inject or dilute into pre‑warmed buffer to form vesicles. Tradeoff: may yield transient mixed micelles; control by temperature and dilution rate.
  • Tert‑butanol freeze‑dry method: co‑dissolve cargo and lipid in t‑BuOH, freeze, and lyophilize to a uniform cake; rehydrate with buffer above Tm (avoids chlorinated solvents).
  • Supercritical CO2 deposition and solvent‑free thin‑film hydration (where equipment exists) minimize solvent residues.

• Comparison (general):

  • Chloroform/methanol: excellent solvency and uniform films; toxicity and waste concerns; requires fume hood and halogenated‑waste disposal.
  • Ethanol: safer, bio‑derived sources available; may need higher temperatures and careful hydration protocols for homogeneous vesicles.
  • Isopropanol: similar to ethanol with slightly lower polarity; slower exchange into aqueous phase.

• Additional sustainability practices:

  • Use amber, reusable glass vials; nitrogen overlay to extend shelf‑life and reduce waste.
  • Plan batch sizes to minimize repeated thaw/aliquot cycles.
  • Choose aqueous buffers prepared with high‑purity water to avoid repeat preparations.

Select the workflow that balances safety, regulatory requirements, and the structural fidelity needed for your membrane model.

Pharmaceutical Uses

No therapeutic claims are made. In formulation research and development, L‑DPPG‑d (or its non‑deuterated analogue) can serve as an excipient or component in lipid‑based delivery systems.

• Roles in experimental formulations (literature/practice):
  • Anionic helper lipid in liposomes to adjust zeta potential, promote colloidal stability, and influence biodistribution in preclinical models.
  • Component in thermally responsive liposomes due to its relatively high Tm, enabling temperature‑triggered release studies.
  • Surface modifier in supported bilayers or coatings to modulate protein adsorption on medical device prototypes (research stage).
• Regulatory/quality considerations:
  • Deuterated lipids are typically used for analytical/biophysical research (e.g., tracer/contrast) rather than as clinical excipients; non‑deuterated PGs may have pharmacopoeial references depending on source and specification.
  • Residual solvent limits, endotoxin/bioburden, and metal content are critical for translational work; Not specified for this item—refer to CoA/Spec Sheet if considering regulated applications.
• Practical guidance:
  • Maintain formulation temperatures above Tm during processing (hydration, extrusion) to ensure homogeneity.
  • Balance with zwitterionic lipids (e.g., PC) and cholesterol to tune membrane rigidity and leakage.

All uses are for research and laboratory development only.

Physical Properties

Item‑specific physicochemical specifications are not provided in the product data. Where helpful, literature/general values for the DPPG class are noted.

• Appearance: Not specified for this item; refer to CoA/Spec Sheet.
• Molecular weight: Not specified for this item; refer to CoA/Spec Sheet. (Note: deuteration increases MW relative to protiated DPPG; extent depends on labeling.)
• Molecular formula: Not specified for this item; refer to CoA/Spec Sheet.
• Melting/phase transition temperature (literature, DPPG):
  • Main gel–fluid transition (Tm) typically around 41–45 °C for dipalmitoyl phosphatidylglycerol in excess water; deuteration can shift Tm slightly upward (few tenths to ~1 °C) depending on labeling extent.
• Solubility (literature/general):
  • Water: insoluble as monomers; forms bilayers/vesicles upon hydration above Tm with agitation or sonication.
  • Organic: soluble in chloroform, dichloromethane, chloroform:methanol (2:1 v/v), and to a lesser extent in pure methanol/ethanol; soluble in tert‑butanol near its mp.
• Critical aggregation: forms lamellar phases and liposomes; anionic headgroup promotes electrostatic interactions with counterions (Na+, Ca2+, Mg2+).
• LogP, pKa, nD, density: Not specified for this item; refer to CoA/Spec Sheet. (Note: PG headgroup pKa values yield −1 charge near neutral pH; exact micro‑pKa context‑dependent, literature.)
• UV/Vis: No strong chromophores; monitor by phosphate assay, evaporative detectors, or MS. (Analytical guidance, literature.)

Always verify item‑specific values on the CoA/Spec Sheet before experimental design.

Quality and Grades

• Grade/Purity for this item: Not specified for this item; refer to CoA/Spec Sheet.
• What to look for in deuterated lipid quality (general guidance):
  • Isotopic enrichment: %D and labeling pattern (uniform tail deuteration, headgroup deuteration, or site‑specific). This dictates contrast in 2H NMR, neutron scattering (SANS), and MS.
  • Chemical purity: typically assessed by HPLC/TLC (>98% area is common in research‑grade lipids; confirm on CoA), minimal lysophospholipid and DAG/TAG impurities.
  • Residual solvent/moisture/peroxide: Not specified for this item; refer to CoA/Spec Sheet. Saturated acyl chains mitigate peroxidation risk relative to unsaturated lipids.
  • Counterion form: PG lipids are often supplied as sodium salts; confirm cation state (Na+, NH4+, etc.) on the CoA, as it affects hydration behavior and zeta potential.
• Recommended QC methods (laboratory, literature):
  • 1H/2H/31P NMR to verify headgroup integrity and deuteration pattern.
  • HRMS (ESI) for molecular ion distribution and deuterium content.
  • TLC with phosphate staining; HPLC‑ELSD/charged aerosol for purity.
  • Phosphate assay for concentration standardization.
• Stabilizers: Not specified for this item; refer to CoA/Spec Sheet.

Interpret the provided CoA/Spec Sheet as authoritative for this SKU; the above outlines typical expectations for high‑end deuterated phospholipids.

Reaction and Applications

This product is primarily used as a functional lipid material rather than a reagent in synthetic organic reactions. Key research applications (literature/practice):

• Model membrane systems:
  • Formation of large/small unilamellar vesicles (LUVs/SUVs), multilamellar vesicles (MLVs), and supported lipid bilayers. The anionic PG headgroup tunes surface charge and protein binding.
• Biophysical studies leveraging deuteration:
  • 2H NMR order parameters for acyl chain dynamics; contrast variation in SANS/NR to resolve leaflet asymmetry, protein insertion, and domain formation.
  • MS tracing of lipid distributions and exchange kinetics without interference from protiated backgrounds.
• Electrostatics and ion interactions:
  • Studies of Ca2+/Mg2+ binding, antimicrobial peptide adsorption/poration, and peripheral membrane protein recruitment (e.g., C2, annexin domains) on anionic bilayers.
• Formulation research:
  • Liposomal encapsulation of hydrophilic cargo (aqueous core) or co‑formulation with helper lipids (e.g., cholesterol) to modulate rigidity and permeability. DPPG contributes negative zeta potential and higher gel Tm for thermal stability.
• Surface science:
  • Langmuir–Blodgett/Langmuir–Schaefer deposition to build anionic monolayers/bilayers with controlled surface pressure–area isotherms.

Practical tips:

• Hydrate above Tm (e.g., 50–60 °C) to ensure fluidity during vesicle sizing; include salt (e.g., 100–150 mM NaCl) to screen charges.
• For deuterium‑sensitive work, avoid protiated contaminants and document D2O/H2O composition to control contrast.
• Store and handle under inert atmosphere to limit hydrolysis; avoid basic aqueous conditions that can cleave ester bonds.

Reaction Conditions

This product is not typically employed as a substrate in chemical reactions; therefore, classical reaction condition guidance (solvent, catalyst, yields) does not apply. Instead, experimental conditions relevant to self‑assembly and sample preparation are provided as general literature guidance.

• Thin‑film hydration (general):
  • Dissolve lipid in CHCl3:MeOH (2:1 v/v), cast a thin film in a round‑bottom flask, evaporate under reduced pressure, and desiccate ≥1 h.
  • Hydrate with buffered saline pre‑heated to 50–60 °C (above Tm), vortex intermittently for 10–30 min.
• Vesicle sizing:
  • Extrusion through 100–200 nm polycarbonate membranes at 50–60 °C; 10–21 passes commonly used. Dynamic light scattering to verify size/PDI.
  • Alternatively, bath or probe sonication above Tm to generate SUVs; avoid metal contamination and overheating.
• Complexation/adsorption studies:
  • For Ca2+/peptide binding, titrate at controlled ionic strength; monitor by zeta potential, ITC, or fluorescence assays.
• Neutron/NMR sample prep:
  • Use D2O or mixed solvents; minimize protiated contaminants; document deuterium fraction and temperature precisely.

These conditions are general literature practices for DPPG‑class lipids and should be optimized for your system. Always consult the item‑specific CoA for any constraints or recommendations.

Safety and Handling

• GHS/SDS data for this specific item:
  • Signal word: Not specified for this item; refer to SDS.
  • Hazard statements: Not specified for this item; refer to SDS.
  • GHS classification and pictograms: Not specified for this item; refer to SDS.
• General safety considerations for phospholipids (literature/practice):
  • Typically low volatility solids/oils; treat as laboratory chemicals. Avoid inhalation of powders/aerosols and contact with eyes/skin.
  • Handle in a fume hood when using organic solvents (e.g., chloroform, methanol) for dissolution/film formation.
  • PPE: lab coat, nitrile gloves, safety glasses; use solvent‑appropriate gloves when handling chlorinated solvents.
  • Incompatibilities: strong oxidizers; avoid prolonged exposure to air/heat/light that can promote acyl chain oxidation (less pronounced with saturated chains such as DP, but good practice still applies). Store under inert gas when possible after opening.
  • First aid (overview; defer to SDS): eye/skin rinse with water for ≥15 min; remove contaminated clothing; if inhaled, move to fresh air; if ingested, rinse mouth. Seek medical attention as needed.
  • Waste: dispose of lipid residues and solvent solutions via organic waste streams per institutional and regulatory guidance.
• Special risks/notes:
  • Deuteration does not materially change acute hazards but is critical for analytical contrast—prevent cross‑contamination with protiated lipids.
  • Use amber vials and minimize freeze–thaw/air cycles to preserve integrity. Consider adding inert gas headspace after each use.

Solvent Selection

L‑DPPG‑d is an amphiphile: hydrophobic saturated C16 tails and an anionic phosphatidylglycerol headgroup. Solvent choice depends on the operation (stock solution, thin‑film formation, or direct hydration).

• Polarity/miscibility profile (literature/general):
  • Readily soluble in chloroform and CHCl3:MeOH mixtures (e.g., 2:1 v/v), which balance tail solvation and headgroup hydrogen bonding.
  • Limited solubility in pure alcohols; tert‑butanol and isopropanol can be used warm for solvent exchange to aqueous media.
  • Insoluble in water as monomers; disperses into bilayers/vesicles upon hydration above Tm with agitation.
• Typical use scenarios:
  • Stock preparation: 5–20 mg/mL in CHCl3:MeOH (2:1). For mass‑spectrometry, use HPLC‑grade solvents; for neutron/NMR, avoid protiated contaminants.
  • Thin‑film hydration: evaporate organic solvent under reduced pressure, then hydrate with buffered saline above Tm.
  • Direct dissolution in ethanol (aqueous‑miscible) followed by dilution into warm buffer minimizes chlorinated solvents (greener workflow).
• Comparison notes:
  • Chloroform vs. ethanol: chloroform gives faster, complete dissolution; ethanol is safer/greener but may require warming and yields different initial aggregate states upon dilution.
  • PG vs. PC lipids: anionic PG headgroups may need higher ionic strength to prevent excessive electrostatic repulsion in vesicles.

Use strictly anhydrous solvents during film casting to prevent premature aggregation; purge with nitrogen and employ amber glassware.

Storage and Reconstitution

• Storage (item‑specific):
  • Store at −20 °C. Protect from light and moisture. Shipped in ice chest with ice pads.
• Long‑term handling (general best practice for lipids):
  • Upon receipt, allow container to equilibrate to room temperature before opening to prevent condensation. Reseal promptly under inert gas (N2/Ar). Keep in amber vials.
  • For multi‑use, prepare single‑use aliquots to minimize freeze–thaw and air exposure. Consider storing dry film or concentrated solutions at −20 °C.
• Reconstitution (general/literature):
  • Organic stocks: dissolve to 5–20 mg/mL in CHCl3:MeOH (2:1) or warm ethanol/isopropanol. Verify clarity; gentle warming may be required with alcohols.
  • Aqueous dispersion: form a thin film from organic solution, dry thoroughly, then hydrate with pre‑warmed buffer (50–60 °C) with vortexing. Size by extrusion/sonication as needed.
  • Concentration verification: use phosphate assay, gravimetry after solvent removal, or ELSD/HPLC. For deuterated materials, 2H NMR can confirm content and labeling integrity.
• Stability:
  • Saturated chains resist oxidation; hydrolysis can occur at elevated pH/temperature. Store neutral pH, avoid bases. Monitor by TLC/HPLC for lysolipid formation over time.
• Specifications not provided:
  • Stabilizers, residual solvent limits, water content: Not specified for this item; refer to CoA/Spec Sheet.

For research use only. Consult the SDS for definitive safety and handling instructions.

Structure and Identity

L‑DPPG‑d is a deuterium‑labeled form of L‑phosphatidylglycerol bearing two palmitoyl (C16:0) chains at the sn‑1/sn‑2 positions of an L‑glycerol backbone and a phospho‑glycerol headgroup. The “‑d” denotes deuterium incorporation for spectroscopic/contrast applications.

• Chemical identity (item‑specific):
  • CAS: L1442148 (catalog reference)
  • Molecular formula: Not specified for this item; refer to CoA/Spec Sheet.
  • Molecular weight: Not specified for this item; refer to CoA/Spec Sheet.
  • SMILES: Not specified for this item; refer to CoA/Spec Sheet.
  • InChIKey: Not specified for this item; refer to CoA/Spec Sheet.
• Structural features (general/literature description):
  • Core scaffold: sn‑glycerol backbone with two ester linkages to palmitic acid (16:0) at sn‑1 and sn‑2.
  • Headgroup: phosphodiester linking to a terminal glycerol (phosphatidylglycerol, PG), providing a net anionic charge (−1) at physiological pH.
  • Stereochemistry: L (sn‑glycerol‑3‑phosphate configuration) typical of natural phospholipids.
  • Functional groups: two fatty acyl esters, one phosphate diester, multiple secondary alcohols in the headgroup.
  • Isotopic labeling: deuterium atoms incorporated (extent and positions typically specified on CoA; not item‑specified here).
• 2D structural description (general):
  • A three‑carbon glycerol spine with the top two carbons bearing long, saturated C16 chains via ester carbonyls; the bottom carbon linked through a phosphate to a second glycerol moiety with two free hydroxyls. Overall amphiphilic: hydrophobic tails + anionic hydrophilic headgroup.

Synthetic Utility

As a fully assembled phospholipid, L‑DPPG‑d is not commonly used as a reagent for constructing small molecules. Its “synthetic utility” lies in materials assembly and surface engineering.

• Materials/building‑block functions (literature/practice):
  • Bottom‑up fabrication of liposomes, polymersomes–lipid hybrids, and supported lipid bilayers with defined anionic character.
  • Langmuir film compression and transfer (LB/LS) to pattern surfaces with controlled packing density and headgroup charge.
  • Mixed‑lipid phase behavior studies (e.g., DPPG/DPPC/Chol) to explore domain formation and mechanical properties.
• Chemical transformations (less common):
  • Headgroup derivatization via coupling to glycerol hydroxyls or phosphate—typically performed on protected intermediates, not on formulated lipids; therefore, L‑DPPG‑d is usually a final material rather than a substrate.
• Retrosynthetic perspective:
  • DPPG is assembled from glycerol, activated palmitoyl derivatives, and a protected glycerol‑phosphate headgroup; deuteration is introduced via deuterated fatty acids or deuterated glycerol precursors. This context is useful for understanding isotopic labeling patterns verified by MS/NMR.

For laboratories focused on molecular assembly, treat L‑DPPG‑d as a precision amphiphile enabling reproducible membrane constructs rather than as a classical synthetic reagent.

Target Specificity

Not applicable. This product is a deuterated phospholipid, not a biological targeting reagent (e.g., antibody, ligand with defined receptor specificity). Any “specificity” arises from its anionic headgroup and membrane incorporation behavior rather than molecular recognition of a discrete biological target.