m-PEG6-azide - ≥98% , CAS No.1043884-49-6

CAS: 1043884-49-6 Cat. No.: M595029 Summenformel: C₁₃H₂₇N₃O₆ Molekulargewicht: 321.4 PubChem CID: 60146162

QUALITÄT & REINHEIT ≥98%

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Application

227,228,229

Übersicht

m-PEG6-azide is a PEG derivative containing an azide group. The azide group can react with alkyne, BCN, DBCO via Click Chemistry to yield a stable triazole linkage. The hydrophilic PEG spacer increases solubility in aqueous media.

Spezifikationen

Spezifikationen & Reinheit

≥98%

Storage

Store at -20°C

Verschickt in

Ice chest + Ice pads

Dieses Produkt erfordert Kühlkettenversand. Grundversand und andere Economy-Optionen sind nicht verfügbar.

Reinheit

≥98%

Namen und Kennungen

Kanonisches Lächeln

COCCOCCOCCOCCOCCOCCN=[N+]=[N-]

IUPAC Name

1-azido-2-[2-[2-[2-[2-(2-methoxyethoxy)ethoxy]ethoxy]ethoxy]ethoxy]ethane

InChIKey

MACROZUHOZGXJL-UHFFFAOYSA-N

INCHI

1S/C13H27N3O6/c1-17-4-5-19-8-9-21-12-13-22-11-10-20-7-6-18-3-2-15-16-14/h2-13H2,1H3

Isomere SMILES

COCCOCCOCCOCCOCCOCCN=[N+]=[N-]

PubChem CID

60146162

Molekulargewicht

321.4

Chemische und physikalische Eigenschaften

• Molekulargewicht: 321.370 g/mol
• XLogP3: 0.200
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 18
• Exact Mass: 321.19 Da
• Monoisotopic Mass: 321.19 Da
• Topological Polar Surface Area: 69.700 Ų
• Heavy Atom Count: 22
• Formal Charge: 0
• Complexity: 264.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 0
• 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 vendor-validated application protocols are specified for this SKU. The following general, literature-based outlines may aid method development; verify and optimize for your system.

• CuAAC labeling of an alkyne-functional peptide/protein:

  1. Prepare m-PEG6-azide at 50–100 mM in anhydrous DMSO.
  2. In PBS or HEPES (pH 7.4), combine biomolecule (10–100 µM) with 2–10 molar equivalents of m-PEG6-azide.
  3. Add CuSO4 (0.2–1 mM), THPTA (0.2–1 mM), then sodium ascorbate (1–5 mM). Mix gently.
  4. React 1–2 h at 25 °C; monitor by LC-MS.
  5. Quench by chelation (EDTA) and remove copper/ligand by desalting or ultrafiltration.

• SPAAC labeling of a DBCO-functional small molecule:

  1. Dissolve partners in PBS with 5–10% DMSO to 1–10 mM (small molecules) or 50–200 µM (biomolecules).
  2. Mix at room temperature for 1–4 h.
  3. Purify by RP-HPLC or appropriate chromatography.

These are starting points only. Scale, stoichiometry, and buffers must be tailored to substrate stability and desired degree of labeling.

Biological Roles

This product is intended for research use only. The following notes describe general, literature-based roles of PEG and azide handles in biochemical workflows; no medical or clinical claims are made.

• PEG as a modifier: Short PEG chains (e.g., PEG6) increase hydrophilicity, reduce nonspecific interactions, and can improve aqueous behavior of small molecules and surfaces in biological assays.
• Bioorthogonal azide: The azide moiety is metabolically rare in native biomolecules, enabling selective ligation to alkyne or cyclooctyne partners in complex mixtures (CuAAC/SPAAC).
• Spacing and flexibility: A 6-unit PEG spacer provides separation between a cargo and a binding/functional domain, often improving accessibility of affinity tags or fluorophores in protein and nucleic acid labeling.
• Minimizing aggregation: Incorporating PEG linkers into nanoparticles, peptides, or oligonucleotides can reduce aggregation and improve dispersion in buffers (literature).
• Assay enablement: m-PEG6-azide facilitates late-stage diversification of probes and surfaces by post-synthetic click attachment of functional modules (dyes, biotin, affinity handles), preserving biological function while tuning solubility.

Note: Any use in live cells, animals, or diagnostics must be independently validated for safety and performance. Consult institutional guidelines and the SDS before use in biological settings.

Buffer Applications

m-PEG6-azide is not a buffering agent and does not define a pH range. However, it is frequently used in buffers for bioorthogonal conjugation.

Practical guidance (literature/general):

• Stock solutions: Prepare 10–100 mM stocks in anhydrous DMSO or DMF. For aqueous use, dilute immediately before reaction to limit hydrolysis or adventitious reduction.
• Common buffers for CuAAC:
  • PBS (pH 7.2–7.6) or HEPES (pH 7.2–7.8) with CuSO4 (0.1–1 mM), sodium ascorbate (0.5–5 mM), and a ligand such as TBTA/THPTA (50–200 µM).
  • Degas buffers to limit oxidative side reactions; include aminoguanidine to scavenge carbonyls when labeling proteins (optional, literature practice).
• Common buffers for SPAAC:
  • PBS, HEPES, or Tris buffers (pH 7–8) are typical; no metal catalyst required. Maintain 1–10% DMSO to help solubilize hydrophobic partners.
• Salt and additives: 100–300 mM NaCl can stabilize proteins; avoid strong nucleophiles or reducing agents that could interfere with azides (e.g., excess DTT can reduce Cu(II) to Cu(I) rapidly; manage stoichiometry accordingly).

Always validate buffer composition against the sensitivity of the target biomolecule (e.g., copper tolerance, ligand compatibility, ionic strength).

Green Alternatives

Green chemistry for m-PEG6-azide focuses on solvent and catalyst choices during conjugation, as the reagent itself is a specialized functional linker.

• Solvent substitution (literature/general):
  • Prefer water or water–ethanol mixtures for click reactions when solubility permits.
  • Replace DMF/DMSO with greener dipolar aprotics such as Cyrene or propylene carbonate where compatible with substrates and catalysts.
• Copper management in CuAAC:
  • Use minimal copper loadings with efficient ligands (e.g., THPTA) to reduce metal waste and improve biocompatibility.
  • Consider heterogeneous copper sources that can be recovered/recycled.
• Copper-free alternatives:
  • SPAAC (DBCO/BCN partners) eliminates copper, reducing metal contamination at the expense of using strained alkynes (often higher E-factor due to synthetic complexity).

Comparison (literature, qualitative):

• Water/EtOH vs DMF/DMSO: lower toxicity and easier solvent recovery; may require cosolvents for hydrophobic partners.
• THPTA-liganded CuAAC vs unliganded CuAAC: higher efficiency at lower copper loadings; mitigates ROS formation in biomolecular settings.
• SPAAC vs CuAAC: avoids metal but uses more complex coupling partners; often preferred for live systems and sensitive proteins.

Operational tips:

• Run reactions at higher concentration to reduce solvent volumes.
• Use aqueous buffers at neutral pH and room temperature to minimize energy inputs.
• Evaluate solvent recycling (rotary evaporation/reuse) for organic phases after purification.

Pharmaceutical Uses

For research use only. No medical or clinical claims are made for this product.

Formulation/manufacturing context (literature/general):

• PEG-based linkers are common tools in discovery and pre-formulation to modulate solubility and reduce nonspecific binding of small-molecule probes and excipients in analytical assays.
• m-PEG6-azide can be used to prototype PEGylated conjugates via click chemistry (CuAAC/SPAAC) during lead optimization, enabling SAR around PEG length and attachment site.
• Surface treatment: Imparting PEGylation to assay plates, sensors, and chromatographic media can reduce fouling and enhance reproducibility in bioanalytical workflows.
• Reference standards: Triazole-linked PEG conjugates prepared from m-PEG6-azide may serve as internal standards or surrogates in method development for LC-MS.

Regulatory/pharmacopeial status:

• No pharmacopeial monograph is implied for this specific linker.
• Any use in GMP settings would require qualification of identity, purity, residual solvents, and elemental impurities per ICH Q3 guidelines; consult the CoA/Spec Sheet and perform in-house verification.

Note: Transition from research-grade linkers to clinical materials requires dedicated synthesis/controls; this SKU is not designated for therapeutic use.

Physical Properties

Item-specific physico-chemical specifications are not provided in the Product Data and should be confirmed on the CoA/Spec Sheet.

• Appearance: Not specified for this item; refer to CoA/Spec Sheet.
• Molecular Weight: Not specified for this item; refer to CoA/Spec Sheet.
• Molecular Formula: Not specified for this item; refer to CoA/Spec Sheet.
• Melting/Freezing Range: Not specified for this item; refer to CoA/Spec Sheet.
• Boiling Point: Not applicable/rarely reported for oligomeric PEG linkers; decomposition or softening typically occurs before a sharp boil (literature, general behavior).
• Density: Not specified for this item; refer to CoA/Spec Sheet.
• Refractive Index: Not specified for this item; refer to CoA/Spec Sheet.
• UV Cutoff: Not specified for this item; refer to CoA/Spec Sheet.

General, literature-based characteristics of PEG6 azides:

• Physical state: often a low-melting solid, waxy solid, or viscous oil depending on exact end-group and purity distribution (literature, general).
• Solubility: highly soluble in water and polar organic solvents (DMSO, DMF, MeOH, EtOH, acetonitrile); limited solubility in nonpolar solvents (hexanes, toluene) (literature, general).
• LogP: strongly negative to near neutral, reflecting high hydrophilicity for short PEG oligomers (literature, general).
• Hygroscopicity: PEG oligomers can be hygroscopic and absorb moisture; handle under dry conditions for sensitive reactions (literature, general).

Always rely on the item’s CoA/Spec Sheet for definitive numerical values and on the SDS for safe handling details.

Quality and Grades

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

Context and expectations for this class of product (literature/general):

• PEG linker quality considerations: Low residual solvents, minimal inorganic salts (e.g., from azide introduction), and narrow oligomer distribution are typically desired for reproducible bioconjugations.
• End-group integrity: High end-group fidelity (methoxy cap on one end, azide on the other) is critical to achieve quantitative coupling. Vendors often verify by NMR and HRMS; consult CoA/NMR traces.
• Metals/UV specifications: Not specified for this item; refer to CoA/Spec Sheet. For click chemistry, low copper background is beneficial when using copper-free protocols.
• Water content: Not specified for this item; refer to CoA/Spec Sheet. Hygroscopic PEGs may carry residual water; drying under high vacuum can improve performance for moisture-sensitive reactions.
• Stabilizers: Typically none are added to PEG linkers; if any stabilizers or counter-ions are used during synthesis or isolation, they should be listed on the CoA/Spec Sheet.

Practical guidance:

• Request a recent CoA for exact purity assay, NMR/LC-MS data, and residual solvent/water where relevant.
• For analytical confirmation, 1H NMR (integration of methoxy singlet and PEG backbone), 13C NMR, IR (azide stretch ~2100 cm−1, literature), and HRMS are commonly used.

Reaction and Applications

m-PEG6-azide is a versatile, bioorthogonal handle used to introduce hydrophilic PEG spacing into small molecules, polymers, surfaces, and biomolecules.

Key applications (literature/general):

• CuAAC “click” chemistry: Azide reacts with terminal alkynes under Cu(I) catalysis to form 1,4-disubstituted triazoles, efficiently linking the PEG6 spacer to alkyne-labeled counterparts (small molecules, dyes, surfaces, polymers).
• SPAAC (copper-free click): Reacts with strained cyclooctynes (e.g., DBCO, BCN) without copper, suitable for sensitive biomolecules and live-cell labeling.
• Staudinger ligation: Reaction with phosphines enables ligation under mild conditions when avoidance of copper or cyclooctynes is desired.
• Surface modification: Grafting to azide-functionalized self-assembled monolayers or polymer backbones; conversely, using m-PEG6-azide to tether to alkyne-bearing substrates to impart antifouling/hydrophilic character.
• Polymer/biopolymer conjugation: Labeling peptides, proteins, and oligonucleotides that carry alkyne/cyclooctyne tags; PEG6 spacing can reduce steric hindrance and improve solubility.

Practical notes:

• For CuAAC, employ CuSO4/sodium ascorbate or pre-formed Cu(I) with stabilizing ligands (e.g., TBTA, THPTA) to minimize oxidative damage to biomolecules.
• For SPAAC, prepare concentrated stocks (e.g., 10–100 mM in DMSO) to facilitate rapid mixing and stoichiometric control.
• Purification often benefits from aqueous-compatible techniques (RP-HPLC, ultrafiltration for biomolecule conjugates).

These uses align with the manufacturer’s general positioning of this reagent as a research-grade PEG-azide building block for conjugation workflows.

Reaction Conditions

Typical, literature-based conditions for reactions of m-PEG6-azide (adjust per substrate and scale):

• CuAAC (azide–alkyne cycloaddition):

  • Solvent: water/DMSO, water/tert-BuOH, or water/DMF mixtures; purely organic (DMF, DMSO, MeCN) for hydrophobic partners.
  • Catalyst: CuSO4 (0.05–1 equiv%) with sodium ascorbate (1–10 equiv%); or pre-formed Cu(I) sources under inert atmosphere.
  • Ligands: TBTA (50–200 µM) or THPTA (100–500 µM) to accelerate and protect biomolecules.
  • Temperature: 20–37 °C; times 0.5–16 h depending on sterics and concentration.
  • Typical outcomes: near-quantitative conversions on small molecules; for biomolecules, 60–95% labeling commonly reported (literature ranges).

• SPAAC (strain-promoted cycloaddition):

  • Partner: DBCO or BCN derivatives.
  • Solvent: aqueous buffers (PBS/HEPES) with 0–10% DMSO.
  • Temperature: 20–37 °C; times 0.5–8 h; faster for BCN > DBCO in many cases (literature-dependent).

• Staudinger reduction/ligation:

  • Reagent: triphenylphosphine or water-soluble phosphines (e.g., TPP, TPPTS).
  • Solvent: aqueous/organic mixtures.
  • Temperature: 20–40 °C; monitor by disappearance of azide IR band (~2100 cm−1).

• Azide → amine conversion:

  • Methods: Staudinger (PPh3/H2O), catalytic hydrogenation (Pd/C, H2), or Zn/NH4Cl reductions (substrate-dependent).

Always perform small-scale trials to optimize equivalents, concentration (often 1–10 mM for bioconjugation), and purification. Protect from oxygen when using reducing systems to limit side reactions.

Safety and Handling

GHS/SDS information is not specified in the Product Data and must be obtained from the SDS for this SKU. The following are general, literature-based safety considerations for PEG-azide linkers.

• GHS classification, pictograms, H-statements: Not specified for this item; refer to SDS.
• General hazards (literature): Organic azides can present risks upon heating, strong impact, or in contact with incompatible materials (e.g., strong reducing agents, certain metals that form heavy-metal azides). Short-chain, alkyl/PEG azides are commonly handled at millimole scale in research labs with appropriate precautions.
• PPE: Use lab coat, safety glasses, and nitrile gloves. Work in a fume hood during weighing, dissolution, and reactions.
• Incompatibilities: Avoid strong acids/bases that could degrade PEG; avoid strong reducing agents that might reduce azides to amines unintentionally; avoid contact with copper salts unless performing CuAAC under controlled conditions.
• Handling tips: Keep material dry; moisture can affect weighing accuracy and reaction stoichiometry. For CuAAC, control copper levels and use stabilizing ligands to minimize side reactions.
• First aid (general): If on skin or in eyes, rinse with plenty of water for several minutes and seek medical attention. If inhaled, move to fresh air. If ingested, seek medical advice. Always follow institutional safety procedures.
• Waste: Collect azide-containing wastes separately if required by local regulations; avoid formation of heavy-metal azides in plumbing. Quench residual azides by appropriate reduction to amines before disposal where permitted.

Defer to the product SDS for authoritative hazard classification and response measures.

Solvent Selection

m-PEG6-azide is a hydrophilic, polar, non-ionic linker with high affinity for polar media.

• Polarity/miscibility (literature):
  • Readily soluble: water, DMSO, DMF, MeOH, EtOH, acetonitrile.
  • Moderately soluble: acetone, isopropanol.
  • Poorly soluble: alkanes (hexane, heptane); limited in toluene/ethyl acetate depending on temperature.
• Selection by application:
  • Bioconjugation in aqueous buffers: dissolve in DMSO/DMF to prepare a concentrated stock, then dilute into PBS, HEPES, or borate buffers for CuAAC/SPAAC.
  • Organic synthesis: anhydrous DMF, DMSO, MeCN, or THF are common. Dry, oxygen-free conditions improve yields for click reactions using copper catalysts.
  • Purification: reverse-phase chromatography (water–acetonitrile) or normal-phase with MeOH/DCM mixtures; preparative HPLC often provides best resolution for short PEGs.
• Comparison (literature):
  • DMSO vs DMF: DMSO offers higher aqueous compatibility and solubilizes many biomolecules; DMF is lower viscosity and easier to remove than DMSO.
  • Water co-solvent systems enable direct labeling of biomolecules while maintaining protein stability (consider buffer salts and pH compatibility with catalysts/ligands).

Tip: Prepare fresh, anhydrous stocks, filter-sterilize if needed for bio-uses, and minimize water content for moisture-sensitive couplings to maintain stoichiometric control.

Storage and Reconstitution

• Storage Conditions (from Product Data): Store at -20 °C.
• Shipping (from Product Data): Shipped in ice chest with ice pads.
• Research Use Note: For research use only.

Handling and reconstitution (general best practice):

• Upon receipt, allow the sealed container to equilibrate to room temperature before opening to minimize moisture condensation.
• If supplied as a solid or viscous oil, dissolve in anhydrous DMSO or DMF to prepare concentrated stock solutions (e.g., 10–100 mM). Water can be used if immediate use is intended.
• Aliquot stocks into dry, inert-atmosphere vials to avoid repeated freeze–thaw cycles. Store aliquots at −20 °C, protected from light and moisture.
• For moisture-sensitive couplings, dry the material under high vacuum prior to use, and handle quickly under dry air or nitrogen.
• Stability: PEG-azides are generally stable at −20 °C; avoid prolonged exposure to elevated temperature, strong acids/bases, or reducing agents that may degrade the azide or PEG chain (literature, general guidance).
• Thawing: Warm aliquots briefly to room temperature to fully dissolve; refreeze unused portions promptly. Discard if signs of decomposition (e.g., loss of azide IR band around ~2100 cm−1, literature) are observed.

Always consult the CoA/Spec Sheet and SDS for item-specific stability and compatibility details.

Structure and Identity

m-PEG6-azide is a monodisperse polyethylene glycol (PEG) linker featuring a terminal azide and a methoxy cap (m-PEG) on the opposite terminus. The scaffold provides six ethylene glycol repeat units, yielding a flexible, hydrophilic spacer that is widely used for bioorthogonal conjugation.

• CAS: 1043884-49-6
• CID: 60146162
• InChIKey: 213714 (as provided)
• 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.

Structural features (general, literature):

• Contains an oligomeric PEG chain with six –CH2–CH2–O– units.
• One terminus is capped with a methoxy group (–OCH3), imparting non-reactive, hydrophilic character.
• Opposite terminus contains an azide group (–N3), a classic bioorthogonal handle for CuAAC (“click”) and strain-promoted cycloaddition (SPAAC) to cyclooctynes.
• 2D description: a linear chain of alternating ethylene and ether oxygen atoms (–O–CH2–CH2–)6, methoxy end-group on one side and an azide-terminated alkoxy/alkyl group on the other.

Stereochemistry: PEG linkers are achiral at the backbone; no stereocenters are present.

Note: Exact atom count, formula, and SMILES can vary by definition of the terminal linkage used to bear the azide; consult the CoA/Spec Sheet for the definitive structure of this SKU.

Synthetic Utility

Functional groups and reactivity (literature/general):

• Azide (–N3): Engages in CuAAC with terminal alkynes (forming 1,4-triazoles), SPAAC with strained alkynes, and Staudinger reductions/ligations with phosphines. Azides can be selectively transformed to amines (e.g., Staudinger or hydrogenation), enabling further derivatization.
• Methoxy-PEG terminus: Inert cap that confers solubility and spacing without introducing additional reactive sites.

Utility in synthesis:

• Convergent assembly: Attach the PEG6 spacer late in a synthesis via click chemistry to tune polarity and PK proxies of small molecules without re-optimizing the core route.
• Polymer modification: Introduce azide-reactive handles on polymers/surfaces, or click the PEG6 azide onto alkyne-bearing matrices to improve wettability and reduce protein adsorption.
• Bioconjugation: Link to alkyne-functionalized biomolecules (peptides, oligos, carbohydrates) under mild conditions with high chemoselectivity.
• Protecting-group orthogonality: Azide survives many standard conditions (e.g., neutral/weakly basic, many hydrogenation-incompatible substrates aside), enabling stepwise installation and late-stage diversification.

Analytical handles:

• IR band near ~2100 cm−1 (azide stretch) provides a quick qualitative check (literature).
• 1H NMR: sharp methoxy singlet and broad PEG multiplets facilitate end-group integration and degree-of-polymerization estimation for quality control.

Together, these features make m-PEG6-azide a practical, modular synthon for installing hydrophilic spacing and bioorthogonal reactivity.

Target Specificity

Not applicable. This product is a small-molecule PEG linker, not an antibody or affinity reagent. No target, epitope, clone, isotype, or species reactivity is defined for this item.

Häufig gestellte Fragen

What is the purity of this product?

This product is supplied at ≥98% purity (chemical assay). Lot-specific values are stated on the Certificate of Analysis.

How should this product be stored?

Store at ?20 °C. Freezer storage is required to maintain the specified shelf life.

How is this product shipped?

This product ships in an insulated container with ice pads. Unpack on arrival and transfer it to the storage condition stated above.

What are the CAS number, molecular formula and molecular weight?

The CAS Number is 1043884-49-6, the molecular formula is C13H27N3O6, and the molecular weight is 321.4 g/mol. InChIKey MACROZUHOZGXJL-UHFFFAOYSA-N.

What documentation is provided?

Available product documentation, including Certificates of Analysis (COA), Safety Data Sheets (SDS), and specification sheets, is shown in the product document area. Document availability and access follow the current site policy.