Mal-amido-PEG2-TFP ester

 CAS No.: 1431291-44-9  Cat No.: BP-500186  Purity: ≥95% 4.5  

Mal-amido-PEG2-TFP ester is a heterobifunctional polyethylene glycol linker designed for PROTAC and related targeted degradation workflows, combining a maleimide-reactive handle with an amide-linked short PEG spacer and a terminal N-hydroxysuccinimide (NHS, TFP) ester for acylation of primary amines. The PEG2 segment provides aqueous solubility and a modest, flexible distance between the two reactive termini, which can reduce steric interference during conjugation. In PROTAC construction, the maleimide group enables chemoselective coupling to thiol-containing ligands (e.g., cysteine residues on proteins or thiol-functionalized targeting moieties) via Michael-type addition, while the TFP ester efficiently forms stable amide bonds with lysine or N-terminal amines on the complementary component. This dual reactivity supports modular assembly of degraders, facilitating rapid generation of conjugates with controlled geometry and improved handling for downstream binding and degradation assays.

Mal-amido-PEG2-TFP ester

Structure of 1431291-44-9

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PROTAC Linker
Molecular Formula
C20H20F4N2O7
Molecular Weight
476.38

* For research and manufacturing use only. Not for human or clinical use.

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Purity
≥95%
Solubility
Soluble in DCM, DMF, DMSO
Storage
Store at 2-8°C
Shipping
Room temperature in continental US; may vary elsewhere.
IUPACName
(2,3,5,6-tetrafluorophenyl) 3-[2-[2-[3-(2,5-dioxopyrrol-1-yl)propanoylamino]ethoxy]ethoxy]propanoate
Synonyms
MAL-PEG2-TFP ester; Mal-NH-PEG2-TFP; 2,3,5,6-tetrafluorophenyl 3-(2-(2-(3-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)propanamido)ethoxy)ethoxy)propanoate; Propanoic acid, 3-[2-[2-[[3-(2,5-dihydro-2,5-dioxo-1H-pyrrol-1-yl)-1-oxopropyl]amino]ethoxy]ethoxy]-, 2,3,5,6-tetrafluorophenyl ester
Boiling Point
640.1±55.0°C at 760 mmHg
Density
1.414±0.1 g/cm3
InChI Key
HHXSYLTYQVHXMA-UHFFFAOYSA-N
InChI
InChI=1S/C20H20F4N2O7/c21-12-11-13(22)19(24)20(18(12)23)33-17(30)4-7-31-9-10-32-8-5-25-14(27)3-6-26-15(28)1-2-16(26)29/h1-2,11H,3-10H2,(H,25,27)
SMILES
C1=CC(=O)N(C1=O)CCC(=O)NCCOCCOCCC(=O)OC2=C(C(=CC(=C2F)F)F)F
ConcentrationVolumeMass1 mg5 mg10 mg
1 mM2.0992 mL10.4958 mL20.9916 mL
5 mM0.4198 mL2.0992 mL4.1983 mL
10 mM0.2099 mL1.0496 mL2.0992 mL

This Mal-amido-PEG2-TFP ester is a bifunctional PROTAC linker designed to connect a maleimide-bearing handle with an activated carboxylate for efficient conjugation. Its PEG spacer supports favorable solubility and conformational flexibility, while the TFP ester enables rapid acylation of nucleophilic groups on targeting ligands. The combination of orthogonal reactivity makes it suitable for assembling targeted protein degradation constructs; the detailed structural and reactivity features are described below.

Structure: The linker contains a maleimide moiety for chemoselective Michael-type addition, an amide linkage, and a short polyethylene glycol spacer that increases hydrophilicity. An activated TFP ester provides an electrophilic carbonyl for acyl transfer, with stable covalent bonds formed upon conjugation.

Reactivity: Use the TFP ester for coupling to primary amines or other suitable nucleophiles under mild, anhydrous-to-semi-aqueous conditions, typically with base to promote nucleophile activation. The maleimide reacts via Michael addition with thiols (or thiol-containing ligands) to form a stable thioether. Perform sequential or orthogonal conjugations by controlling order, pH, and solvent compatibility; common coupling solvents include DMF or DMSO, with careful exclusion of competing thiols during TFP activation.

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Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2

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g/mol
Tip: Chemical formula is case sensitive. C22H30N4O c22h30n40
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