THP-PEG13-OH , CAS No.T1447903

CAS: T1447903 Cat. No.: T1447903 분자식: C₃₁H₆₂O₁₅ 분자량: 674.81

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

개요

THP-PEG13-OH is a PEG-based PROTAC linker that can be used in the synthesis of PROTACs.

Specifications

보관 조건

Store at -20°C

배송

Ice chest + Ice pads

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이름과 식별자

분자량

674.81

Application Protocols

No application protocols (e.g., WB, IHC, IF, FC) are applicable to this chemical linker as sold.

• For synthetic use, follow standard organic protocols for:
  • End-group activation (tosylation/mesylation), nucleophilic substitution, carbonate/carbamate couplings.
  • THP deprotection under mild acid catalysis.
• Refer to the Reaction Conditions and Synthetic Utility sections for literature-based conditions and planning guidance.

Biological Roles

This product is intended for research and synthetic use; no biological activity is claimed.

General background (literature/general):

• Poly(ethylene glycol) (PEG) segments are widely used as hydrophilic, flexible spacers in biochemical and materials research due to their water compatibility, low protein adsorption, and ability to modulate the hydrodynamic radius of conjugates.
• A defined-length PEG13 spacer can be employed to tune separation between a core scaffold and a functional headgroup, often improving aqueous handling and reducing nonspecific binding in assay reagents, immobilized ligands, and biosensors.
• The THP group serves as a temporary, acid-labile protection for an alcohol, enabling orthogonal synthetic sequences that ultimately furnish diols or further functionalized termini.

Research examples (no medical/clinical claims):

• Construction of bifunctional linkers after selective activation of the free –OH, followed by THP deprotection to unmask the second –OH for subsequent conjugation.
• Preparation of amphiphilic constructs (e.g., PEGylated small molecules or labels) to improve solubility in assay buffers.

Note:

• If the reagent is incorporated into biological probes or surfaces, residual acid used for THP removal should be thoroughly removed/neutralized to avoid impacting biomolecules.
• Endotoxin/bioburden specifications, if relevant to your workflow, are not provided and should be confirmed separately for sensitive applications.

Buffer Applications

This material is not a buffering agent and is not typically used to prepare pH buffer systems.

• Practical note (literature/general): PEGylated linkers may affect solution viscosity and macromolecular crowding at higher concentrations, but THP-PEG13-OH itself does not provide defined buffering capacity.
• If used as part of an assay reagent or surface modifier, prepare buffers independently (e.g., PBS, HEPES, Tris) and confirm compatibility with any acid-mediated THP deprotection steps conducted prior to biological use.

Green Alternatives

Considering typical transformations with THP-PEG13-OH, greener choices often involve solvent and reagent selection rather than changing the linker itself.

Opportunities (literature/general):

• Solvent substitution:
  • Replace DCM/CHCl3 with 2-MeTHF, CPME, EtOAc, or green alcohols (EtOH) when compatible with the transformation and THP stability.
  • Use ACN or propylene carbonate as greener polar aprotics in place of DMF/DMSO where feasible (mind viscosity and workup).
• Catalysis and reagents:
  • For THP deprotection, opt for catalytic PPTS in green alcohols (EtOH) at ambient temperature instead of strong mineral acids in halogenated solvents.
  • Use organic carbonates (e.g., dimethyl/diethyl carbonate) or CDI as carbonylation reagents in place of phosgene derivatives for carbonate/carbamate formation.
• Energy and workup:
  • Perform reactions at ambient temperature and under concentrated conditions to reduce energy and solvent volumes.
  • Employ aqueous ethanol or EtOAc for extractions to minimize chlorinated waste.

Illustrative comparison (general):

• DCM + TsCl/pyridine vs 2-MeTHF + TsCl/DIPEA: 2-MeTHF reduces chlorinated waste and may improve safety profile; monitor rate/selectivity.
• DMF for azidation vs ACN/green polar aprotics: ACN can perform comparably with easier removal; ensure solubility of salts (add phase-transfer agents if needed).

Note: Always validate green substitutions with small-scale trials to confirm THP integrity and reaction performance.

Pharmaceutical Uses

For research use only. No clinical or therapeutic uses are claimed or supported.

Formulation/manufacturing context (literature/general):

• Defined-length PEG linkers like PEG13 are commonly employed in the research phase to explore structure–property relationships in prodrug linkers, ADC spacers, and surface modifiers. The THP group allows staged synthesis prior to installing final functional heads.
• Potential roles in pre-formulation research include:
  • Solubility enhancers when appended to hydrophobic small molecules.
  • Spacers in affinity ligands or tags used during analytical method development.
• Regulatory/compendial status: Not specified for this item; refer to CoA/Spec Sheet. Any transition to regulated use would require comprehensive validation (identity, purity, Mn/Đ, residuals) and compliance with pharmacopeial/ICH guidelines.

Practical considerations:

• Thorough removal of deprotection acids and reagents is essential before any contact with biological matrices.
• If used to build PEGylated excipient-like materials in research, document end-group identity and residual solvent levels to support reproducibility.

Physical Properties

Item-specific physicochemical specifications are not provided in the Product Data.

• 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 point / Boiling point / Density / Refractive index / UV cutoff / Water/peroxide/metal limits: Not specified for this item; refer to CoA/Spec Sheet.

Literature/general expectations for context (not item specifications):

• PEG oligomers around the PEG13 range typically have average Mn in the several-hundred-dalton range and may present as low-melting waxy solids or viscous liquids, depending on end-groups and dispersity.
• Solubility profile (general):
  • High solubility in polar organic solvents (THF, DCM, acetone, MeOH, EtOH, acetonitrile, DMF, DMSO).
  • Miscibility with water increases with PEG length; THP end-capping slightly reduces water miscibility versus diol analogs.
• Partitioning: PEG chains are hydrophilic; end-capping with THP increases hydrophobic character modestly (logP effects depend on exact Mn and polydispersity). These are comparative trends only.

Notes:

• For rigorous method development (e.g., HPLC, LC–MS), obtain exact Mn, dispersity (Đ), and any stabilizers/residuals from the CoA.
• Hygroscopicity is common for PEG oligomers; measured water content (e.g., Karl Fischer) should be consulted on the CoA when critical.

Quality and Grades

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

How to interpret quality for THP-PEG13-OH (general guidance):

• Purity reporting for discrete PEG oligomers often includes:
  • Mn (number-average molecular weight) and Đ (dispersity). Lower Đ indicates higher monodispersity and more predictable performance in conjugations.
  • Residual volatile content (e.g., solvents), water content (Karl Fischer), and inorganic residues.
  • Identity confirmation by 1H/13C NMR and HRMS/ESI-MS; end-group analysis is critical for protected PEGs.
• Chromatographic grades (e.g., HPLC-grade solvent) are not applicable to the reagent itself, but low UV-absorbing impurity content can matter if used in photochemical steps or monitored by UV detection.
• Stabilizers: Not typically required for PEG oligomers; however, strictly neutral storage avoids acid-catalyzed THP loss. If any stabilizer or inhibitor is present, it will be specified on the CoA.

What to check on receipt (best practice):

• Confirm end-group integrity (presence of THP signals in 1H NMR; diagnostic acetal protons ~4.5–5.5 ppm, literature) and the free OH at the opposite terminus (broad signal; or by end-group titration).
• Review water content and residual acid/base to avoid premature deprotection or side reactions.
• Verify that the reported Mn is appropriate for your spacer-length requirements.

Reaction and Applications

THP-PEG13-OH functions as a hydrophilic spacer/linker with one protected terminus, enabling stepwise, chemoselective elaboration.

Representative applications (literature/general):

• Acid-labile protecting strategy: The THP group masks one terminus during selective functionalization of the free –OH (e.g., activation, coupling). Subsequent mild acid deprotection reveals the second –OH for further diversification.
• Spacer installation: Introduce a defined-length PEG13 unit between small molecules, surfaces, or ligands to modulate solubility, flexibility, and reduce nonspecific interactions.
• End-group activation and substitution:
  • Tosylate/mesylate formation at the free –OH, followed by SN2 with azide (to give PEG13–N3 for click chemistry), halides, thiols, or amines (via subsequent Staudinger or reductive steps).
  • Carbonate or carbamate linkages via CDI or DSC to couple with amines or phenols.
• Surface and solid-support modification: Grafting onto silica, polymers, or nanoparticles after suitable activation (e.g., silanization plus PEG coupling) to create antifouling coatings.
• Bioconjugation workflows: PEG13 provides a medium-length, flexible tether that can reduce steric hindrance and improve aqueous behavior of conjugates (research use only).

Practical tips:

• Maintain neutral to basic conditions when working with the THP-protected terminus to prevent premature deprotection.
• Verify end-group fidelity by NMR before critical coupling steps.
• For high-efficiency SN2 on activated PEGs, dry polar aprotic solvents and phase-transfer catalysts can improve conversions.

Reaction Conditions

General, literature-based guidance for common manipulations with THP-PEG13-OH (not product-specific specifications):

• Tosylation/mesylation (activation of free –OH):
  • Typical: TsCl (1.1–1.5 equiv) or MsCl (1.2–1.5 equiv), base (2–3 equiv; pyridine, Et3N, or DIPEA) in anhydrous DCM/THF, 0°C to rt, 1–16 h. Monitor by TLC/NMR.
• Azidation of –OTs/–OMs:
  • NaN3 (2–4 equiv) in dry DMF or ACN, 50–80°C, 2–24 h. Work up carefully due to toxicity of azide salts; avoid heavy-metal contact.
• Carbonate formation (CDI route):
  • CDI (1.1–1.5 equiv) in anhydrous DCM/THF, rt to 40°C, 1–3 h to form imidazolyl carbonate, then add nucleophile (amine/phenol) with base.
• THP deprotection (unmask second –OH):
  • PPTS (5–10 mol%) or CSA (1–10 mol%) in MeOH/EtOH/acetone/DCM, 0–25°C, 0.5–6 h. Avoid strong acids and elevated temperatures that may risk PEG degradation.
• Esterification to carboxylic acids:
  • DCC/DMAP or EDCI/DMAP in DCM/THF, 0°C to rt, 2–16 h. For aqueous compatibility, use EDCI/NHS strategies post-activation.

Operational tips:

• Use anhydrous conditions; PEGs are hygroscopic and water suppresses activation yields.
• Employ minimal heating to preserve THP integrity unless deprotection is intended.
• Purification: silica gel chromatography with polar modifiers (MeOH or isopropanol in DCM/EtOAc) may be required; add a small amount of triethylamine to suppress tailing of PEGs.

Safety and Handling

GHS/SDS information specific to this item is not provided in the Product Data and should be consulted on the product SDS.

• GHS classification, pictograms, signal word, H-statements: Not specified for this item; refer to SDS.

General laboratory guidance (literature/general):

• PEG oligomers are typically of low acute toxicity but should be handled with standard laboratory precautions.
• The THP ether is acid-labile. Avoid strong acids or prolonged exposure to acidic conditions during handling and storage to prevent unintended deprotection and release of the corresponding alcohol.
• PPE: use lab coat, safety glasses, and appropriate chemically resistant gloves (e.g., nitrile). Work in a fume hood when performing reactions or handling solvents/reagents.
• Incompatibilities: strong acids (deprotect THP), strong oxidizers (may degrade ethers/PEG), and moisture when handling under anhydrous conditions for synthesis.
• First aid (overview; defer to SDS):
  • Skin/eye contact: rinse with water for at least 15 minutes; remove contaminated clothing; seek medical attention if irritation persists.
  • Inhalation (dust/aerosol): move to fresh air; seek medical attention if symptoms occur.
  • Ingestion: rinse mouth; do not induce vomiting; seek medical advice.
• Waste: collect PEG-containing residues and acidic/organic waste per institutional and local regulations.
• Special risks: PEGs can retain residual solvents/acid traces; ensure neutral work-up and adequate drying before storage to prevent slow THP cleavage.

Solvent Selection

This reagent is a PEG-based linker bearing one THP-protected terminus and one free hydroxyl. Solvent choice is driven by the intended transformation (e.g., deprotection, activation, coupling) and the need for anhydrous conditions.

General solvent behavior (literature/general):

• Polarity/miscibility: Highly soluble in polar organic solvents (THF, DCM, acetone, MeOH, EtOH, ACN, DMF, DMSO). Water miscibility increases with PEG length; THP end-capping slightly reduces water affinity.
• Dry solvents are preferred for activation steps (e.g., tosylation/mesylation, CDI-mediated carbonate formation, carbonyldiimidazole reactions).
• Acid-sensitive THP ether disfavors protic acids and strongly acidic media during manipulations unrelated to deprotection.

When to choose specific solvents:

• Deprotection (acid-catalyzed): MeOH, EtOH, acetone, THF, or DCM with catalytic PPTS or CSA; select a solvent that dissolves the substrate and allows mild acid catalysis.
• End-group activation (tosylation/mesylation): anhydrous DCM, CHCl3, or THF with bases such as pyridine, triethylamine, or DIPEA.
• Nucleophilic substitutions (after activation to OTs/OMs): DMF, DMSO, or ACN to solubilize salts (e.g., NaN3) and promote SN2.
• Carbonate/carbamate formation: DCM or THF with CDI, or phosgene surrogates (e.g., triphosgene) under inert atmosphere.

Comparison (literature/general):

• DCM vs 2-MeTHF: 2-MeTHF offers greener profile and good solubility for PEGs; DCM provides ease of removal and classic conditions but with higher environmental and safety burdens.
• DMF/DMSO enable high polarity; consider ACN or green polar aprotics (e.g., propylene carbonate) where feasible.

Storage and Reconstitution

• Storage conditions (item-specific): Store at -20°C (from Product Data). Protect from moisture and acids to preserve the THP protecting group. Keep container tightly closed.
• Shipping (item-specific): Shipped in ice chest with ice pads (from Product Data).

Best practices (literature/general):

• Atmosphere: Store under inert gas (nitrogen/argon) if possible. PEG oligomers are hygroscopic; minimize headspace and use desiccants.
• Light: Ambient light is generally acceptable, but opaque or amber containers can help minimize any incidental photolysis of sensitive impurities.
• Thawing/handling: Allow container to equilibrate to room temperature in a dry environment before opening to prevent condensation.

Reconstitution and use:

• Solubility: Typically readily soluble in dry THF, DCM, acetone, MeOH/EtOH, ACN, DMF, and DMSO (literature/general). For strictly anhydrous work, use freshly dried/degassed solvents.
• Stock solutions: Prepare at convenient concentrations (e.g., 10–100 mg/mL) depending on viscosity and downstream reaction stoichiometry. Store solutions refrigerated or frozen when compatible with solvent and THP stability; limit freeze–thaw cycles.
• Stability: Avoid acidic environments during storage. For long-term storage, periodic QC by 1H NMR to confirm THP integrity is recommended.

Research use note (item-specific): For research use only (from Product Data).

Structure and Identity

Overview of a protected PEG linker suitable for organic synthesis and bioconjugation workflows.

• Item-specific identifiers (from Product Data):

  • SKU: T1447903
  • Product Name: THP-PEG13-OH
  • CAS: T1447903 (catalogue identifier; not a registry CAS)
  • InChIKey: Not specified for this item; refer to CoA/Spec Sheet.
  • SMILES: Not specified for this item; refer to CoA/Spec Sheet.
  • Molecular Formula: Not specified for this item; refer to CoA/Spec Sheet.
  • Molecular Weight: Not specified for this item; refer to CoA/Spec Sheet.

• Structural features (interpretation based on common nomenclature; literature/general):

  • “PEG13” denotes an oligomeric polyethylene glycol chain comprising 13 ethylene glycol repeat units, i.e., –[CH2–CH2–O]13–.
  • “THP” indicates a 2-tetrahydropyranyl ether protecting group at one terminus (acid-labile acetal from 3,4-dihydro-2H-pyran), commonly used to mask an alcohol.
  • “–OH” indicates a free terminal hydroxyl group on the opposite end of the PEG chain.
  • Expected topology: HO–(CH2CH2O)13–O–THP (monofunctional PEG: one free primary alcohol, one THP-protected alcohol as a tetrahydropyranyl ether).
  • Key functional groups: primary alcohol (nucleophilic, enables further derivatization), internal ether linkages (PEG backbone), and an acetal (THP ether, acid-labile).

• 2D structure in words (literature/general): a linear PEG chain of 13 –CH2–CH2–O– units; one terminus ends in –CH2–CH2–OH, the other is linked via –O– to a tetrahydropyran ring (saturated six-membered oxygen heterocycle). No stereocenters are typically specified for THP ethers used as protecting groups.

Synthetic Utility

THP-PEG13-OH provides a protected–free alcohol pair on a medium-length PEG chain, enabling orthogonal, sequence-controlled synthesis.

Key transformations (literature/general):

• Selective activation at the free –OH:
  • Tosylate/mesylate formation (TsCl/MsCl + base), enabling SN2 with azide, halides, thiolates, or other nucleophiles.
  • Carbonate/carbamate formation via CDI, DSC, or carbonate esters to couple with amines/phenols.
  • Silane or silyl ether formation if temporary masking of the free –OH is required.
• THP deprotection to unmask the second –OH:
  • Catalytic PPTS, CSA, or dilute mineral acids in MeOH/EtOH/acetone/DCM at 0–25°C typically suffice.
  • Post-deprotection diol enables symmetric or asymmetric further functionalization (e.g., one end to carboxylic acids via esterification; the other to amines via carbamates).
• Divergent synthesis from a common intermediate:
  • Convert the activated –OTs to –N3, then reduce to –NH2 (Staudinger or hydrogenation) to introduce amine-terminated PEG13 while retaining the protected end for later unveiling.
  • Introduce click handles (alkyne/azide) to build modular bioconjugation scaffolds.

Practical notes:

• Control stoichiometry and base strength to avoid incidental THP cleavage; monitor by TLC/NMR.
• Dry, oxygen-free conditions often improve yields and minimize PEG backbone oxidation in oxidative couplings.

Target Specificity

Not applicable. This product is a small-molecule/oligomeric linker, not a biological targeting reagent such as an antibody or aptamer.

• Antigen/epitope, species reactivity, clone, isotype: Not applicable.
• If incorporated into a targeting construct, any specificity derives from the appended ligand, not from THP-PEG13-OH itself.