Name: THP-PEG4-Pyrrolidine(N-Me)-CH2OH
Brand: BOC Sciences
Rating: 5 (1 reviews)

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-20°C, stored under nitrogen; In solvent, -80°C, 6 months; -20°C, 1 month (stored under nitrogen)

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Room temperature in continental US; may vary elsewhere.

IUPACName

[(2S,4R)-1-methyl-4-[2-[2-[2-[2-(oxan-2-yloxy)ethoxy]ethoxy]ethoxy]ethoxy]pyrrolidin-2-yl]methanol

InChI Key

WSIXZTYJDDDXDX-PAMZHZACSA-N

InChI

InChI=1S/C19H37NO7/c1-20-15-18(14-17(20)16-21)25-12-10-23-8-6-22-7-9-24-11-13-27-19-4-2-3-5-26-19/h17-19,21H,2-16H2,1H3/t17-,18+,19?/m0/s1

SMILES

CN1CC(CC1CO)OCCOCCOCCOCCOC2CCCCO2

1. Mono-, Di- and Tetra-iron Complexes with Selenium or Sulphur Functionalized Vinyliminium Ligands: Synthesis, Structural Characterization and Antiproliferative Activity

Gabriele Agonigi, Lucinda K Batchelor, Eleonora Ferretti, Silvia Schoch, Marco Bortoluzzi, Simona Braccini, Federica Chiellini, Lorenzo Biancalana, Stefano Zacchini, Guido Pampaloni, Biprajit Sarkar, Paul J Dyson, Fabio Marchetti Molecules. 2020 Apr 3;25(7):1656. doi: 10.3390/molecules25071656.

A series of diiron/tetrairon compounds containing a S- or a Se-function (2a-d, 4a-d, 5a-b, 6), and the monoiron [FeCp(CO){SeC1(NMe2)C2HC3(Me)}] (3) were prepared from the diiron μ-vinyliminium precursors [Fe2Cp2(CO)( μ-CO){ μ-η1: η3-C3(R')C2HC1N(Me)(R)}]CF3SO3 (R = R' = Me, 1a; R = 2,6-C6H3Me2 = Xyl, R' = Ph, 1b; R = Xyl, R' = CH2OH, 1c), via treatment with S8 or gray selenium. The new compounds were characterized by elemental analysis, IR and multinuclear NMR spectroscopy, and structural aspects were further elucidated by DFT calculations. The unprecedented metallacyclic structure of 3 was ascertained by single crystal X-ray diffraction. The air-stable compounds (3, 4a-d, 5a-b, 6) display fair to good stability in aqueous media, and thus were assessed for their cytotoxic activity towards A2780, A2780cisR, and HEK-293 cell lines. Cyclic voltammetry, ROS production and NADH oxidation studies were carried out on selected compounds to give insights into their mode of action.

THP-PEG4-Pyrrolidine(N-Me)-CH2OH is a polyethylene glycol–based PROTAC linker featuring a THP-protected alcohol and a tertiary N-methyl pyrrolidine motif. Its ether-rich, flexible scaffold supports favorable ternary-complex formation and improved solubility, while the masked hydroxyl enables controlled conjugation strategies during PROTAC assembly. The following sections describe the linker’s structural characteristics and practical reactivity considerations for constructing targeted protein degraders.

Structure: The linker contains a PEG ether chain providing conformational flexibility and hydrophilicity, coupled to a THP-protected primary alcohol. A N-methyl pyrrolidine ring introduces a tertiary amine center, enabling stable attachment points and tunable polarity. Ether, acetal, and secondary/tertiary amine functionalities define its chemical behavior.

Reactivity: The THP-protected hydroxymethyl group is typically compatible with standard PROTAC synthesis steps that require orthogonal protection. Deprotection to regenerate the alcohol can be achieved under mild acidic conditions or via established acetal-removal protocols, followed by nucleophilic substitution or coupling to install the desired warhead/ligand handle. The tertiary amine supports base-mediated steps, and reactions are commonly performed in polar aprotic solvents with acid/base control to preserve the PEG ether and amine integrity.

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It is commonly abbreviated as: C₁V₁ = C₂V₂