OMs-PEG2-NHAlloc-PEG2-Boc , CAS No.2376332-47-5

CAS: 2376332-47-5 Cat. No.: O1445587 Formula: C₂₂H₄₁NO₁₂S Peso molecolare: 543.63

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Panoramica

OMs-PEG2-NHAlloc-PEG2-Boc is a PROTAC linker. OMs-PEG2-NHAlloc-PEG2-Boc can be used in synthesis PROTAC SMARCA2/4-degrader-28.

Specifications

Condizioni di conservazione di stoccaggio

Store at -20°C

Spedito in

Ice chest + Ice pads

Questo prodotto richiede spedizione a catena fredda. I servizi di terra e altri servizi economici non sono disponibili.

Nomi e identificatori

Peso molecolare

543.63

Application Protocols

No assay or immunoassay protocols are specified for this item. Application is via standard organic synthesis and conjugation workflows.

• General workflow examples (informational):
  • Mesylate substitution: dissolve linker in dry MeCN, add nucleophile and base, stir to completion, then purify by flash chromatography.
  • Sequential deprotection/coupling: Pd^0 Alloc removal → amide coupling (HATU/DIPEA) → acidolytic Boc removal → final coupling.

For detailed, step-by-step procedures, adapt standard literature protocols to your substrates and consult the SDS/CoA for handling constraints.

Biological Roles

This is a synthetic PEG linker and does not have inherent biological roles. Any biological relevance arises only after it is incorporated into conjugates.

• General notes (informational):

  • PEG spacers can improve solubility and reduce nonspecific interactions in biomolecule conjugates (literature), but effects depend on the final construct.
  • Alloc/Boc orthogonality allows site-selective assembly of probes or affinity reagents; no intrinsic bioactivity is implied.

• Item-specific: No biological function is specified for this item; it is supplied strictly for research use and synthetic applications.

Buffer Applications

Not typically used as a buffer component. This linker is intended for organic-phase synthesis and conjugation chemistry.

• Practical tip:
  • If aqueous handling is required (e.g., for bioconjugation), dissolve first in a miscible organic co-solvent such as DMF or DMSO before gradual addition to the buffered aqueous phase to avoid precipitation.

Green Alternatives

Greener choices focus on solvent and reagent selection, as the linker’s intrinsic composition is fixed.

• Solvent choices (greener options; literature/general):

  • Prefer EtOAc, 2-MeTHF, CPME, or MeTHF/DCM blends over chlorinated solvents when compatible.
  • For SN2 at mesylate: MeCN and propylene carbonate can replace DMF/NMP in some cases; ensure nucleophile solubility.
  • Alloc deprotection: carry out in 2-MeTHF or EtOAc with catalytic Pd^0 and safer hydride donors (e.g., polymethylhydrosiloxane, PMHS) instead of PhSiH3.

• Comparative view (general guidance):

  | Step | Conventional | Greener alternative | Trade-offs | |---|---|---|---| | SN2 substitution | DMF/NMP | MeCN or propylene carbonate | Solubility of bulky nucleophiles may decrease in MeCN | | Alloc removal | DCM + PhSiH3 | 2-MeTHF + PMHS | Reaction rate can be slower; optimize Pd loading | | Boc deprotection | DCM/TFA | EtOAc or MeOH with TFA (minimal volume) | Workup more aqueous waste |

• Waste minimization:

  • Run reactions at higher concentration (viscosity permitting); use solid-supported scavengers for Pd and amines to reduce aqueous washes.
  • Recycle solvents where validated; employ micro-scale scouting to minimize material use.

Pharmaceutical Uses

No excipient or pharmacopeial status is provided for this item, and it is not intended for therapeutic use.

• Item-specific:

  • Research Use Note: For research use only.

• General formulation context (informational):

  • PEG linkers are often explored in R&D for conjugate spacing and solubility modulation. Any translation to GMP manufacturing would require sourcing GMP-grade material with full QC, impurity profiling, elemental analysis, and residual solvent controls—not specified for this item.

Physical Properties

Comprehensive physico-chemical specifications are not provided with this listing; typical behavior below is based on literature for short PEG linkers and the named protecting groups.

• 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.

• Literature/typical attributes for PEG2 linkers with carbamates (informational, not product specifications):

  • Physical state: usually low-melting waxy solid or viscous oil depending on exact MW and counter-groups.
  • Solubility: good in polar aprotic organics (DMF, DMSO, acetonitrile, DCM); limited in nonpolar hydrocarbons; miscibility with water varies and is often modest for protected derivatives.
  • Hydrogen-bond donors/acceptors: multiple ether oxygens (acceptors) and carbamate carbonyls (acceptors), protected N–H generally non-basic.
  • LogP: typically low to moderate due to PEG content; exact value depends on end groups (not specified for this item).
  • pKa: carbamate-protected amines are non-basic; deprotected amines (post-treatment) are basic with pKaH ~9–10 (literature, not applicable to protected form).
  • Thermal behavior: protecting groups (Alloc, Boc) decompose under strong acid/base or high heat; avoid prolonged temperatures >50–60 °C during handling.

• Refractive index, density, BP/MP: Not specified for this item; refer to CoA/Spec Sheet.

Quality and Grades

This product is supplied for research use only; specific analytical grade or purity is not provided in the product data.

• Item-specific:

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

• Guidance on typical quality controls for PEGylated linkers (general):

  • Identity confirmation: 1H/13C NMR (PEG methylenes, Boc tert-butyl singlet, Alloc allyl signals, mesylate methyl), HRMS/ESI, and IR (carbamate C=O ~1690–1720 cm−1; sulfonate S=O ~1350/1170 cm−1).
  • Purity assessment: HPLC or UPLC with ELSD/UV (PEGs show weak UV; Alloc/Boc enhance UV at 210–230 nm).
  • Residual solvents/water/peroxides: Not specified for this item; refer to CoA/Spec Sheet.

• Stabilizers/additives: Not specified for this item; refer to CoA/Spec Sheet.

• What the grade implies (general):

  • Research-grade PEG linkers are typically suitable for organic synthesis and bioconjugation development. For GMP or clinical manufacturing, request GMP-grade material and full regulatory support (not offered by this listing).

Reaction and Applications

Designed as a modular, orthogonally protected PEG linker enabling stepwise assembly and bioconjugation.

• Heterobifunctional design (literature/inferred):

  • Terminal mesylate: electrophile for SN2 coupling with thiols (as RS−), azides (NaN3), halides (Finkelstein-type), carboxylates, or amines to install diverse handles (e.g., thiol, azide, alkyne after further transformation).
  • Alloc-protected amine: selectively deprotect under Pd^0 catalysis (e.g., Pd(PPh3)4) in the presence of Boc to unveil a nucleophilic amine for subsequent acylation, carbamate/urea formation, or NHS ester coupling.
  • Boc-protected amine: orthogonal to Alloc; remove with TFA or HCl to reveal a terminal amine for final conjugation.

• Typical application flows:

  • Install partner A via mesylate substitution → Alloc deprotect → couple to partner B (e.g., NHS ester on a biomolecule mimic) → optional Boc deprotect for a third functionalization.
  • Convert mesylate to azide (NaN3), then reduce to amine (Staudinger or catalytic hydrogenation) to generate diamine-PEG spacing with orthogonal protection retained.

• Practical notes:

  • Maintain anhydrous conditions during mesylate substitution to avoid hydrolysis to alcohol.
  • Use orthogonal deprotection: Pd^0 for Alloc (with scavengers) and TFA/acid for Boc; sequence deprotections to match partner stability.
  • Monitor by LC/MS; PEG increases hydrophilicity, aiding solubility with polar partners.

Reaction Conditions

Typical conditions below are literature guidance for the functional groups present and must be optimized for each substrate.

• SN2 substitution at the mesylate (general):

  • Solvent: dry DMF or MeCN (0.05–0.3 M).
  • Nucleophiles: NaN3 (1.2–2.0 eq), alkali thiolates (1.2–1.5 eq), secondary amines (1.2–2.0 eq) with base (DIPEA/K2CO3).
  • Temperature/time: 0–60 °C, 2–16 h depending on nucleophile; monitor by LC/MS.
  • Notes: Minimize water to suppress hydrolysis; add phase-transfer catalysts for less soluble nucleophiles if needed.

• Alloc deprotection (Pd^0-mediated; general):

  • Reagents: Pd(PPh3)4 (2–10 mol%), phenylsilane or PMHS (3–5 eq) as scavenger, or morpholine as nucleophile trap.
  • Solvent: DCM, THF, or DMF; rt to 40 °C; 0.5–2 h.
  • Notes: Scrub residual Pd with scavenger resins or dithiocarbamate wash; Boc group remains intact under these conditions.

• Boc deprotection (general):

  • Reagents: TFA (50–100% v/v in DCM or MeOH) or 4 M HCl/dioxane.
  • Conditions: 0–25 °C, 0.5–2 h.
  • Notes: Quench into cold ether to precipitate amine salts; protect acid-sensitive partners accordingly.

• Workup/purification:

  • Avoid high temperatures during solvent removal; use reduced pressure at ≤30–35 °C.
  • Purify by flash chromatography with polar modifiers; ELSD/charged aerosol detection aids tracking due to low UV of PEG.

Safety and Handling

Handle as a research chemical bearing an alkyl sulfonate ester (mesylate) and carbamate protecting groups.

• Item-specific hazard info:

  • Signal word: Not specified for this item; refer to SDS.
  • GHS classification: Not specified for this item; refer to SDS.
  • H-statements/Pictograms: Not specified for this item; refer to SDS.

• General safety considerations (literature/chemistry-based):

  • Mesylates are electrophilic; avoid skin contact and inhalation of dust/aerosol; may be irritant.
  • Carbamates can hydrolyze under strong acid/base; avoid incompatible reagents that may release CO2 or alcohols.
  • Potential for alkylation: prevent contact with strong nucleophiles in biological tissue; use appropriate containment.

• PPE and handling:

  • Wear lab coat, nitrile gloves, and splash goggles; handle in a fume hood.
  • Use dry techniques; keep containers closed to minimize moisture ingress that can hydrolyze mesylate.

• Incompatibilities (general):

  • Strong bases/nucleophiles will consume the mesylate; strong acids/bases can cleave Boc/Alloc; avoid azides without controls.

• First-aid (summary; defer to SDS):

  • Skin/eye contact: rinse with water for 15 minutes; remove contaminated clothing; seek medical advice.
  • Inhalation: move to fresh air; seek medical attention if symptoms persist.
  • Ingestion: rinse mouth; do not induce vomiting; seek medical attention.

• Waste: collect as halogen-free organic waste unless process introduces halogens; follow institutional rules.

Solvent Selection

Choose solvents that solubilize PEG segments while preserving protecting groups and minimizing mesylate hydrolysis.

• Polarity and miscibility (literature/general):

  • Polar aprotic solvents provide excellent solubility: DMF, DMSO, NMP, acetonitrile, and DCM.
  • Moderate solubility in THF/EtOAc; limited in hexanes/toluene unless warmed.
  • Water: protected PEG linkers often have limited aqueous solubility; use co-solvents (DMF, DMSO) if aqueous conditions are unavoidable.

• Selection guidance (use-case oriented):

  • SN2 substitution at the mesylate: anhydrous DMF/MeCN favor bimolecular substitution by enhancing nucleophile activity; add base as needed.
  • Pd^0 Alloc deprotection: DCM, THF, or DMF commonly used with scavengers (e.g., morpholine, PhSiH3); avoid protic solvents that can quench catalysts.
  • Boc deprotection: DCM or MeOH with TFA; include scavengers to capture cations formed.

• Small comparison (general):

  • DMF vs MeCN: DMF offers higher solubility for larger conjugation partners; MeCN provides cleaner workups and faster SN2 kinetics with some nucleophiles.
  • DCM vs THF: DCM is gentle and compatible with TFA deprotections; THF is preferred when subsequent nucleophilic substitutions or base-sensitive partners are present.

Storage and Reconstitution

Follow cold-chain handling to preserve protecting groups and suppress hydrolysis.

• Item-specific (from Product Data):

  • Storage conditions: Store at −20 °C.
  • Shipped in: Ice chest + ice pads.

• General handling guidance:

  • Protect from moisture and prolonged light exposure; keep container tightly closed under dry inert gas if possible.
  • Allow to warm to room temperature in a sealed container before opening to avoid condensation.
  • For solution prep, use anhydrous solvents (DMF, DMSO, MeCN, DCM). Prepare small aliquots to minimize freeze–thaw cycles; store solutions at −20 °C when compatible and use within a few days.

• Stability notes:

  • Mesylate can hydrolyze to alcohol in the presence of water; avoid aqueous storage.
  • Alloc and Boc groups are stable at −20 °C in neutral, dry environments but will cleave under their respective deprotection conditions.

• Reconstitution: Not applicable for lyophilized buffers; dissolve directly in a suitable anhydrous organic solvent at the desired concentration.

Structure and Identity

A heterobifunctional PEGylated linker bearing an alkyl mesylate (electrophile), an Alloc-protected secondary amine, and a Boc-protected amine, separated by short PEG2 spacers.

• Item-specific (from Product Data):

  • Product name: OMs-PEG2-NHAlloc-PEG2-Boc
  • CAS: 2376332-47-5
  • 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 (literature/inferred from name):

  • Functional groups: terminal alkyl mesylate (–OSO2CH3), two carbamate-type N-protecting groups: Alloc (allyloxycarbonyl) on an internal –NH–, and Boc (tert‑butoxycarbonyl) on a terminal amine.
  • Linker backbone: two discrete ethylene glycol repeat units on each side (PEG2 segments), providing hydrophilicity and spacing.
  • Electrophilic terminus (OMs) enables SN2 substitution with soft to medium nucleophiles; Alloc and Boc provide orthogonal, chemoselective deprotection handles.

• 2D description (literature/inferred):

  • One terminus is –(CH2CH2O)2–OMs; progressing inward to a secondary –NH– protected as Alloc (–NH–COO–CH2–CH=CH2), then another –(CH2CH2O)2– spacer terminating in a Boc-protected amine (–NH–COO–tBu).

• Stereochemistry: none expected in the PEG segments or protecting groups; the compound is achiral (literature/inferred).

Synthetic Utility

Orthogonally protected, short-PEG linker enabling sequential functionalization under mutually compatible conditions.

• Key functional handles (literature/inferred):

  • Mesylate (–OMs): primary electrophile for SN2, enabling installation of diverse termini (e.g., halides, azides, thioethers, ethers, secondary amines).
  • Alloc–NH–: Pd^0-labile carbamate protecting group orthogonal to Boc and to many acid/base-sensitive motifs.
  • Boc–NH–: acid-labile protection (TFA/HCl) orthogonal to Alloc/Pd^0 and many basic conditions.

• Representative transformations:

  • Mesylate → azide (NaN3, DMF/MeCN), then → amine (Staudinger or H2/Pd): provides a protected diamine scaffold.
  • Mesylate → thioether via thiolate substitution (RS−): introduces thiol-reactive or thiol-containing motifs for further click-type couplings.
  • Free amine (post-deprotection) → urea/carbamate via CDI, DSC, or triphosgene analogs; → amide via EDC/HATU couplings.

• Retrosynthetic value:

  • Serves as a modular spacer between a nucleophile-installed headgroup (from OMs) and two amines unmasked in sequence, enabling precise ordering of assembly in multi-component syntheses and bioconjugations.

Target Specificity

Not applicable. This product is a small-molecule linker and does not exhibit biological target specificity on its own. No antigen/epitope, clone, or isotype information applies.

Domande frequenti

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 2376332-47-5, the molecular formula is C22H41NO12S, and the molecular weight is 543.63 g/mol.

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.