2-Phthalimidehydroxy-acetic acid
2-Phthalimidehydroxy-acetic acid is a bifunctional linker building block featuring a phthalimide-derived aromatic scaffold connected to a hydroxyacetic acid motif, enabling controlled spacing and chemical handle(s) for PROTAC assembly. Structurally, it provides a rigid, electron-poor phthalimide unit that can contribute to productive geometry and stability, while the hydroxy and carboxylic acid functionality supports covalent coupling to adjacent ligands or to other linker segments via standard esterification or amide-forming chemistries. In targeted protein degradation designs, such linkers are used to tune the relative orientation and effective reach between an E3 ligase–binding moiety and a target-binding ligand, thereby influencing formation of the ternary complex and the efficiency of ubiquitination-driven degradation. As a research reagent, it is valuable for constructing PROTACs and related conjugates where robust linker chemistry and predictable functional-group reactivity are required for systematic structure–activity studies.
Structure of 134724-87-1
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This PROTAC linker, 2-Phthalimidehydroxy-acetic acid, provides a chemically stable scaffold for connecting ligands through a functionalized acetic acid motif. Its phthalimide-derived framework supports robust handling and predictable coupling behavior, which can simplify linker synthesis and downstream assembly of bifunctional degraders. The following sections describe its structural features and practical reactivity considerations relevant to constructing targeted protein degradation tools.
Structure: The linker contains a phthalimide core bearing a hydroxylated acetic acid substituent. It features an imide carbonyl system conjugated within an aromatic ring, plus an aliphatic hydroxyl and carboxylic acid group. These functionalities enable strong hydrogen-bonding and provide orthogonal handles for bioconjugation-style coupling.
Reactivity: For PROTAC assembly, the carboxylic acid can be converted to an activated ester or acylating intermediate using standard peptide-coupling chemistries, enabling amide-bond formation with appropriately functionalized ligand partners. The hydroxyl group may be leveraged for further derivatization under conditions that preserve the imide stability. Typical couplings proceed in polar aprotic solvents with base, following established acyl-transfer mechanisms used for linker-ligand conjugation.
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
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