Name: N-(2-Aminoethyl)maleimide Trifluoroacetate Salt
Brand: BOC Sciences
Rating: 5 (1 reviews)

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Price

Stock

Quantity

$--

In stock

Appearance

White powder

Storage

Powder, -20°C, 3 years; 4°C, 2 years; In solvent, -80°C, 6 months; -20°C, 1 month

Shipping

Room temperature in continental US; may vary elsewhere.

IUPACName

1-(2-aminoethyl)pyrrole-2,5-dione;2,2,2-trifluoroacetic acid

Synonyms

1-(2-aminoethyl)pyrrole-2,5-dione;2,2,2-trifluoroacetic acid; 1-(2-aminoethyl)pyrrole-2,5-dione;2,2,2-trifluoroacetic acid

Boiling Point

278.1 °C at 760 mmHg

InChI Key

YNHKVOGCDPODMT-UHFFFAOYSA-N

InChI

InChI=1S/C6H8N2O2.C2HF3O2/c7-3-4-8-5(9)1-2-6(8)10;3-2(4,5)1(6)7/h1-2H,3-4,7H2;(H,6,7)

SMILES

C1=CC(=O)N(C1=O)CCN.C(=O)(C(F)(F)F)O

1. One-pot two-step radiosynthesis of a new (18)F-labeled thiol reactive prosthetic group and its conjugate for insulinoma imaging

Xuyi Yue, Xuefeng Yan, Chenxi Wu, Gang Niu, Ying Ma, Orit Jacobson, Baozhong Shen, Dale O Kiesewetter, Xiaoyuan Chen Mol Pharm. 2014 Nov 3;11(11):3875-84. doi: 10.1021/mp5001857.Epub 2014 May 12.

N-(2-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)ethyl)-6-fluoronicotinamide ([(18)F]FNEM), a novel prosthetic agent that is thiol-specific, was synthesized using a one-pot two-step strategy: (1) (18)F incorporation by a nucleophilic displacement of trimethylammonium substrate under mild conditions; (2) amidation of the resulting 6-[(18)F]fluoronicotinic acid 2,3,5,6-tetrafluorophenyl ester with N-(2-aminoethyl)maleimide trifluoroacetate salt. The radiosynthesis of the maleimide tracer was completed in 75 min from [(18)F]fluoride with 26 ± 5% decay uncorrected radiochemical yield, and specific activity of 19-88 GBq/μmol (decay uncorrected). The in vitro cell uptake, in vivo biodistribution, and positron emission tomography (PET) imaging properties of its conjugation product with [Cys(40)]-exendin-4 were described. [(18)F]FNEM-Cys(40)-exendin-4 showed specific targeting of glucagon-like peptide 1 receptor (GLP-1R) positive insulinomas and comparable imaging results to our recently reported [(18)F]FPenM-Cys(40)-exendin-4.

N-(2-Aminoethyl)maleimide trifluoroacetate salt, provides a maleimide handle for efficient thiol-directed conjugation and a primary amine for orthogonal functionalization. Its zwitterionic salt form improves handling and reproducibility in linker assembly workflows. The combination of reactive motifs supports modular PROTAC synthesis, enabling rapid attachment to cysteine-bearing ligands and subsequent coupling steps, as detailed below.

Structure: The linker contains a maleimide electrophile conjugated to a two-carbon aminoethyl spacer, paired with a primary amine functionality. It is supplied as a trifluoroacetate salt, featuring ionic interactions that enhance aqueous solubility. Key bonds include amide-linked connectivity and a cyclic alkene within the maleimide core.

Reactivity: Maleimide groups react selectively with thiols via Michael addition, forming stable thioether linkages under mildly basic to neutral aqueous conditions. Trifluoroacetate counterions generally support dissolution and controlled reactivity without requiring harsh reagents. For PROTAC construction, thiol-containing ligands or cysteine-derivatized intermediates are combined with the linker, typically with careful pH control to favor conjugation while minimizing side reactions.

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