THP-PEG10-Boc , CAS No.T1445509

CAS: T1445509 Cat. No.: T1445509 Formule: C₃₁H₆₀O₁₄ Poids moléculaire: 656.80

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Vue d’ensemble

THP-PEG10-Boc is a PEG-based PROTAC linker that can be used in the synthesis of PROTACs.

Specifications

Conditions de stockage de stockage

Store at -20°C

Expédié en

Ice chest + Ice pads

Ce produit nécessite l'expédition en chaîne froide. Les services terrestres et autres services économiques ne sont pas disponibles.

Noms et identifiants

• Poids moléculaire: 656.80

Application Protocols

No application protocols are provided for this item. As a general starting point for common transformations (literature guidance; not product specifications):

• THP deprotection (to reveal –OH): Dissolve substrate in MeOH (0.05–0.2 M), add PPTS (5–10 mol%), stir at rt and monitor by LC–MS. Upon completion, neutralize with NaHCO3, concentrate, and purify by column or precipitation.
• Boc deprotection (to reveal –NH2): Cool a DCM solution (0.05–0.2 M) to 0°C, add TFA (1–5 eq or up to 50% v/v), stir 0.5–2 h at 0–25°C. Evaporate volatiles, co-evaporate with toluene, then basify and extract to obtain the free amine.
• Amide coupling: Dissolve carboxylic acid partner and the deprotected amine in DMF or DCM, add HATU (1.2 eq) and DIPEA (3 eq), stir at 0–25°C until completion. Work up and purify (consider reverse-phase methods for PEGylated products).

Note: These are general literature procedures provided for experienced chemists. Validate and optimize conditions for your specific substrates and scales.

Biological Roles

Item-specific biological data are not provided. The following describes general roles of PEG linkers in biochemical research (no clinical/medical claims):

• PEG as an inert spacer: Short PEG chains (~10 EO units) serve as hydrophilic, flexible tethers to modulate spacing between a biomolecule and a label/surface, often reducing nonspecific interactions and aggregation.
• End-group masking and staged unveiling: THP masking of an alcohol and Boc masking of an amine allows sequential, chemoselective exposure of functional groups for bioconjugation workflows (e.g., first reveal –OH to introduce an azide, then reveal –NH2 for amide coupling to an NHS-activated protein under buffered conditions).
• Solubility tuning: Incorporation of PEG10 can improve aqueous compatibility of otherwise hydrophobic ligands without significantly impacting their recognition motifs (context-dependent; empirical verification required).
• Reduced protein adsorption on materials: PEGylated surfaces are widely used to minimize protein fouling; heterobifunctional PEGs enable anchoring to one surface while presenting a reactive group to the environment after deprotection.

Caveats and best practices:

• Residual acid or scavengers from deprotection (e.g., TFA salts) should be removed thoroughly before exposure to biological systems to avoid denaturation or assay interference.
• Verify endotoxin/bioburden if using in sensitive bioassays; for this SKU, such data are Not specified for this item; refer to CoA/Spec Sheet.

Buffer Applications

This product is a protected PEG linker and is not a buffering agent. It does not define or maintain pH in solution.

Practical notes for work in buffered systems (general guidance):

• After appropriate deprotection and purification, the unveiled amine (–NH2) can be used for conjugation in aqueous buffers (e.g., phosphate, HEPES) via NHS-ester chemistry; maintain pH 7.5–8.5 for optimal amide formation while minimizing hydrolysis.
• The unveiled alcohol (–OH) typically requires prior activation (e.g., to carbonate or NHS-carbonate) before aqueous coupling; such activations are commonly performed in organic solvents and then introduced into buffered media.

If you require a buffering component, select a dedicated buffer system (e.g., PBS, HEPES, MOPS) appropriate to your pH range and compatibility with your biomolecules.

Green Alternatives

While THP-PEG10-Boc itself is a specialized linker, greener choices often center on solvent selection and protecting-group strategy rather than the PEG chain.

Greener solvent options (literature guidance):

• Prefer ethyl acetate, 2-methyltetrahydrofuran (2-MeTHF), cyclopentyl methyl ether (CPME), or dimethyl carbonate over chlorinated solvents when feasible.
• Use aqueous ethanol or isopropanol for THP deprotection when compatible with stability of other moieties; catalytic PPTS or CSA at ambient temperature can reduce energy input.

Protecting-group considerations:

• THP and Boc are both acid-labile; minimizing strong acid usage (e.g., short TFA exposure, or gaseous HCl alternatives under controlled conditions) can reduce corrosive waste.
• Alternative end-group strategies (e.g., Fmoc instead of Boc for base-labile deprotection) may provide orthogonality that avoids harsh acids; trade-offs include use of amines/piperidine (worker exposure) and potential PEG base sensitivity.

Comparison (general, not item-specific):

• DCM vs 2-MeTHF: similar solvation for many organics; 2-MeTHF is bio-based and has better environmental metrics but forms peroxides—monitor and inhibit as needed.
• DMF/DMSO vs propylene carbonate: propylene carbonate is safer but more viscous and less volatile; suitability depends on coupling chemistry.

Operational green tips:

• Run at higher substrate concentrations to cut solvent volume.
• Employ solid-supported reagents/scavengers to simplify workup and reduce solvent washes.
• Recover/recycle solvents (EtOAc, CPME) where facility capabilities permit.

Pharmaceutical Uses

No pharmacopeial status or excipient designation is provided for this item. Use is restricted to research and laboratory applications.

General, non-clinical context for PEG linkers (informational):

• Process development tools: Heterobifunctional PEGs are used in discovery and process R&D to prototype conjugation strategies (e.g., spacing between actives and carriers, attachment to polymer/scaffold backbones) before any formulation development.
• Materials modification: Installation on particles, membranes, or device surfaces to modulate hydrophilicity and reduce nonspecific binding during analytical method development.
• Precursor to functional handles: Following deprotection, the amine and alcohol ends can be derivatized to pharmaceutically relevant motifs (e.g., maleimides, NHS-esters, azides) for subsequent research-grade conjugation.

Important limitations:

• No therapeutic, diagnostic, or clinical claims are made for this product.
• Compliance aspects typical of pharmaceutical excipients (e.g., USP/NF monographs, residual solvent limits per ICH Q3C, elemental impurities per ICH Q3D, endotoxin/bioburden controls) are Not specified for this item; refer to CoA/Spec Sheet if such attributes are required for your application.

Physical Properties

Item-specific physico-chemical specifications have not been provided for this SKU. Refer to the CoA/Spec Sheet for authoritative values.

Item-specific (from 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.

General/literature expectations for PEG10 end-capped linkers (informational only; not product specifications):

• Physical state: typically a waxy solid or viscous, colorless to pale oil at ambient temperature, depending on end-groups and exact polydispersity.
• Solubility: high solubility in polar aprotic solvents (DCM, THF, EtOAc, DMF, DMSO); moderate in alcohols (MeOH, EtOH); water solubility varies and usually decreases with hydrophobic end-caps (THP, Boc).
• Hygroscopicity: PEG segments can be mildly hygroscopic; dry handling recommended.
• Refractive index and density: similar to other short PEG oligomers; values depend on chain length and capping groups (literature; not specified for this item).
• Boiling/melting behavior: oligomeric PEGs often show broad softening/melting ranges rather than sharp melting points (literature; not specified for this item).

Notes for users:

• If exact values (e.g., MW distribution, polydispersity, water content, residual solvents) are critical for synthesis or analytical methods, please consult the item’s CoA/SDS or request the specification sheet prior to use.

Quality and Grades

Item-specific grade and purity are not provided in the Product Data.

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

General guidance on grades for PEG linkers (informational):

• Research or synthetic grade: Suitable for routine organic synthesis and linker installation; may have broader molecular weight distribution and typical residual solvent/moisture levels.
• Bioconjugation grade / high-purity grade: Tight control of polydispersity (Đ), low endotoxin/bioburden, and low UV-absorbing impurities; often subjected to additional purification (e.g., preparative chromatography) and stringent release testing.
• HPLC grade designation (when applicable to solvents) refers to low UV background; for solid/oligomeric linkers, high-purity claims typically mean high assay by NMR/HPLC/LC–MS with defined MW distribution.

What to check on the CoA for this item:

• Assay/purity method (HPLC, NMR integration) and acceptance criteria.
• Average molecular weight and distribution for PEG10, if reported.
• Residual solvents, water content (Karl Fischer), and inorganic content (ash/metals), if applicable.
• Identity confirmation (1H/13C NMR, MS) and functional end-group verification (e.g., presence of Boc and THP signals).

If your application requires bioconjugation-grade material (e.g., protein modification), request documentation on endotoxin/bioburden and residual scavengers (e.g., TFA) prior to use.

Reaction and Applications

THP-PEG10-Boc is designed as a modular spacer for stepwise functionalization, enabling controlled exposure of either a terminal alcohol (from THP) or a primary amine (from Boc) for downstream coupling.

Representative application sequences (literature/general guidance):

• Selective THP deprotection → alcohol unveiling: Treat with catalytic PPTS in MeOH (rt) to liberate the terminal hydroxyl while retaining Boc under mild conditions. The alcohol can be activated (e.g., tosylation/mesylation) and transformed to azide/thiol or used to form carbonates/urethanes.
• Boc deprotection → amine unveiling: Expose to TFA/DCM (e.g., 1:1) at 0–25°C to reveal the primary amine salt. The –NH2 can be coupled to carboxylic acids (amide formation via HATU/EDC/HOAt/HOBt), isocyanates (urea linkages), or carbonyls (reductive amination after suitable derivatization).
• Bidirectional assembly: Combine the above to install two different handles on each terminus, producing heterobifunctional linkers for surface modification, polymer–small molecule conjugation, or affinity tag spacing.

Use cases:

• Creation of PEGylated building blocks with defined spacer length (n≈10) to tune hydrophilicity, reduce aggregation, or improve solubility of conjugates.
• Installation of cleavable junctions: carbonate/urethane formation at the alcohol terminus can introduce hydrolytically or enzymatically labile linkages.
• Materials and surface chemistry: attachment of the amine end to activated surfaces (NHS-esters) while preserving the THP-masked alcohol for subsequent grafting.

Practical notes:

• Maintain anhydrous, neutral conditions during protection-preservation steps.
• Sequence planning is key: employ mild acid for THP removal first if Boc retention is desired; reserve strong acids last for Boc removal.

Reaction Conditions

The following are general, literature-reported conditions for chemistries relevant to THP-PEG10-Boc. They are provided as guidance only and are not product specifications.

• THP deprotection (unmask –OH):

  • Reagents: PPTS (5–10 mol%) in MeOH or EtOH.
  • Conditions: 20–25°C, 1–4 h; monitor by TLC/LC–MS. Boc generally survives short exposure to these mild acids.
  • Alternative: AcOH (10–30% v/v) in THF/H2O or MeOH at rt to 40°C; adjust time to avoid Boc loss.

• Boc deprotection (unmask –NH2):

  • Reagents: TFA/DCM (1:1 to 9:1), or HCl/dioxane (4 M).
  • Conditions: 0–25°C, 0.5–2 h (TFA) or as needed; quench and remove volatiles; convert amine salt to free base with suitable workup.

• Alcohol activation and substitution:

  • Tosylation: TsCl (1.1–1.5 eq), pyridine or Et3N, DCM, 0°C→rt, 2–6 h.
  • Mesylation: MsCl (1.1–1.5 eq), Et3N, DCM, 0°C→rt, 1–3 h.
  • Azidation: NaN3 (2–4 eq), DMF, 60–90°C, 2–16 h; then Staudinger/hydrogenation to amine if desired.

• Amide coupling (after Boc removal):

  • HATU (1.1–1.5 eq), DIPEA (2–4 eq), DMF or DCM, 0–25°C, 1–4 h.
  • EDC·HCl (1.1–1.5 eq) with HOAt/HOBt and base in DMF/DCM, 0–25°C.

Typical outcomes:

• Yields depend on substrate and purification strategy; PEGylated products often require reverse-phase or size-exclusion cleanup due to tailing in normal-phase chromatography.

Always monitor reactions (TLC, LC–MS, NMR) and optimize stoichiometry/temperature based on your substrate set.

Safety and Handling

Authoritative safety information must be taken from the product SDS.

Item-specific hazard data (from Product Data):

• GHS Classification: Not specified for this item; refer to SDS.
• Signal Word: Not specified for this item; refer to SDS.
• H-Statements: Not specified for this item; refer to SDS.
• Pictograms: Not specified for this item; refer to SDS.

General laboratory safety guidance for PEG linkers with acid-labile protecting groups (informational; not product-specific):

• Likely hazards: May cause skin/eye irritation. Avoid inhalation of dust/aerosols and contact with skin/eyes.
• PPE: Wear lab coat, nitrile gloves, and safety goggles. Use in a chemical fume hood when weighing, dissolving, or performing deprotection/coupling reactions.
• Incompatibilities: Avoid strong acids/bases during storage; both THP and Boc groups are acid-sensitive (Boc particularly to strong acids, THP to mild acids). Avoid prolonged exposure to moisture, which can promote hydrolysis of end-groups.
• First aid (general): If on skin/eyes, rinse with plenty of water for ≥15 minutes. If inhaled, move to fresh air. If ingested, rinse mouth and seek medical attention. Always follow the SDS.
• Special handling: Keep container tightly closed under dry inert atmosphere when possible. Use anhydrous solvents during synthesis to prevent premature deprotection.
• Waste: Dispose of solutions and residues according to institutional and local regulations. Segregate acid-containing deprotection waste (e.g., TFA) from amine-containing streams.

Always defer to the SDS and institutional EHS policies for final guidance.

Solvent Selection

Selection should balance solubility of the PEG core with stability of the acid-labile THP and Boc end-groups.

General/literature guidance (informational; not product specifications):

• Polarity/miscibility: PEG10 linkers dissolve readily in polar aprotic solvents (DCM, THF, EtOAc, DMF, DMSO) and many alcohols. Water miscibility decreases with hydrophobic end-caps (THP, Boc) but may still be moderate for short PEGs.
• Stability considerations: Avoid acidic media during storage/stock solutions. Boc can be cleaved by strong acids (e.g., TFA, HCl in dioxane). THP is cleaved by mild acids (cat. PPTS, AcOH). Neutral anhydrous solvents are preferred when handling the protected linker.

Typical choices by task:

• Weighing/stock solutions: Anhydrous DCM, THF, or acetonitrile for short-term handling; DMF/DMSO for higher concentrations or for coupling setups.
• Coupling to carboxylic acids (after Boc removal to reveal –NH2): DMF, DCM, or NMP with carbodiimide or uronium reagents; add base (DIPEA) as needed.
• THP deprotection (to reveal –OH): MeOH or EtOH with catalytic PPTS; solvent should solubilize both substrate and acid catalyst.
• Aqueous workups: Ethyl acetate or MTBE often extract these linkers efficiently from mildly aqueous mixtures; DMF/DMSO require salting-out or back-extraction.

Small comparison (literature-based):

• DCM vs THF: DCM offers rapid dissolution and easy removal; THF provides better compatibility with base-sensitive systems and low temperature operations.
• DMF/DMSO: Maximize solubility but harder to remove; reserve for coupling steps or when necessary.

Storage and Reconstitution

Item-specific storage and shipping (from Product Data):

• Storage Conditions: Store at -20°C.
• Shipped In: Ice chest + Ice pads.

General handling guidance for this class of compounds:

• Protect from moisture and acids to prevent premature deprotection of THP and Boc end-groups. Store tightly closed under inert gas (e.g., nitrogen or argon) with desiccant.
• Allow container to equilibrate to room temperature before opening to minimize condensation.

Reconstitution and stock solutions (general; not product specifications):

• Solvents: Dissolve in anhydrous DCM, THF, acetonitrile, DMF, or DMSO. Choose solvent based on the planned reaction and stability of protecting groups.
• Typical concentrations: 10–100 mM for reaction stocks; higher in DMF/DMSO if needed.
• Filtration: If particulates are present, pass through a PTFE syringe filter (0.2–0.45 µm) under dry conditions.

Stability notes:

• Avoid prolonged exposure to strong acids or bases in solution; both THP and Boc are acid-labile, with Boc particularly sensitive to strong acids (e.g., TFA). Neutral, anhydrous media extend shelf-life of solutions.
• For long-term storage, prefer the dry solid at -20°C. Prepare fresh solutions immediately prior to use.

Research Use Note: For research use only.

Structure and Identity

THP-PEG10-Boc is a heterobifunctional polyethylene glycol (PEG) linker featuring an acid-labile tetrahydropyranyl (THP) protecting group on one terminus and a tert-butyloxycarbonyl (Boc)-protected amine on the other.

• SKU: T1445509
• Product Name: THP-PEG10-Boc
• CAS: Not specified for this item; refer to CoA/Spec Sheet.
• 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 from name; general/literature description):

• Contains approximately 10 ethylene glycol repeat units (–CH2–CH2–O–)n providing a flexible, hydrophilic spacer.
• One terminus bears a THP ether (a 2-tetrahydropyranyl acetal protecting group) masking a terminal alcohol; this group is typically cleavable under mild acidic conditions.
• The opposite terminus carries a Boc-protected primary amine (–NH–CO–O–tBu); the Boc carbamate is removable with stronger acids such as TFA.
• No stereocenters are expected within the PEG chain; the THP ring is a saturated six-membered heterocycle.

2D structure in words (general):

• A linear PEG chain of ~10 oxyethylene units with: (a) a terminal O–THP ether; (b) a terminal –NH–CO–O–tBu (Boc) connected through a short linker to the PEG chain. The molecule is amphiphilic: PEG core is polar/protic-compatible, end-groups are acid-labile protecting groups enabling orthogonal (or semi-orthogonal) deprotections.

Synthetic Utility

THP-PEG10-Boc offers a convergent route to heterobifunctional constructs by staged unmasking of a terminal alcohol and a primary amine.

Functional group strategy (literature/general guidance):

• THP end (masked –OH): Mild acid deprotection (e.g., PPTS in MeOH) yields a primary alcohol. Subsequent transformations include:
  • Sulfonate activation (TsCl or MsCl) → nucleophilic substitution to azide (NaN3), thiolates, halides.
  • Carbonate/urethane formation using CDI, DSC (disuccinimidyl carbonate), or chloroformates to introduce cleavable linkages or NHS-activated carbonates for bioconjugation.
  • Oxidation to aldehyde (e.g., Dess–Martin, Swern) for oxime/Schiff base formation, followed by reductive stabilization.
• Boc end (masked –NH2): Strong-acid deprotection (e.g., TFA) reveals a primary amine suitable for:
  • Amide coupling to carboxylic acids (EDC/HOBt, HATU/HOAt) or to NHS-esters on surfaces/biomolecules.
  • Urea/thiourea formation with (thio)isocyanates, or carbamate with activated carbonates.

Orthogonality and sequencing:

• THP can often be removed under milder conditions that leave Boc intact, enabling selective unveiling of –OH first. Final Boc removal exposes –NH2 for a second coupling step.

Advantages of a PEG10 spacer:

• Provides hydrophilicity and flexibility, improves solubility of hydrophobic conjugates, and reduces steric hindrance around reactive sites, often enhancing coupling efficiency.

Target Specificity

Not applicable. This product is a small-molecule PEG linker and does not have biological target specificity, antigen reactivity, clone, or isotype. No target-related data are provided for this item.