Product Manager: Selina Zhang; Email: selina@coreychem.com
| Product Name | Benzenepropanoic acid, 4-[[[(1,1-dimethylethoxy)carbonyl]amino]methyl]-α,α-dimethyl- |
| Synonyms | Benzenepropanoic acid, 4-[[[(1,1-dimethylethoxy)carbonyl]amino]methyl]-α,α-dimethyl- |
| CAS NO | 2241131-18-8 |
| Purity |
99% |
| Appearance |
/ |
| MF | C17H25NO4 |
| MW | 307.38 |
| Contact | selina@coreychem.com |
Benzenepropanoic acid, 4-[[[(1,1-dimethylethoxy)carbonyl]amino]methyl]-α,α-dimethyl- (CAS: 2241131-18-8) is a highly valuable bifunctional building block widely used in medicinal chemistry, targeted protein degradation, and bioconjugate development. Featuring a unique molecular scaffold that combines a sterically hindered α,α-dimethylpropanoic acid moiety with a Boc‑protected aminomethylbenzyl group, it offers orthogonal protection, enhanced metabolic stability, and excellent compatibility with solid‑phase and solution‑phase synthesis. Its primary applications are outlined below:
1. Targeted Protein Degradation (PROTACs) & Conjugate Chemistry
Key Linker for PROTAC Design
This compound serves as a versatile linker component in the construction of proteolysis‑targeting chimeras (PROTACs). The Boc‑protected amine allows selective deprotection and subsequent conjugation to an E3 ligase ligand (e.g., VHL, CRBN), while the carboxylic acid couples to the target protein ligand. The α,α‑dimethyl substitution reduces unintended esterase or protease cleavage, improving linker stability in cellular and in vivo settings.
Antibody‑Drug Conjugate (ADC) and Peptide‑Drug Conjugate (PDC) Development
The orthogonal functional groups enable the attachment of cytotoxic payloads (via the acid) and targeting vectors (via the amine after Boc removal). Researchers use this scaffold to generate cleavable or non‑cleavable linkers with tunable hydrophilicity and pharmacokinetic properties, supporting ADC/PDC hit optimization and lead characterization.
2. Medicinal Chemistry & Drug Discovery
Conformationally Hindered Spacer Unit
The α,α‑dimethyl group adjacent to the carboxylic acid imparts a gem‑dimethyl effect, increasing rigidity and reducing off‑target hydrolysis. This makes the compound an ideal spacer for improving the metabolic stability of peptide‑drug conjugates, dimeric ligands, and bifunctional probes in neurological and oncological research programs.
Building Block for Library Synthesis
With its well‑defined Boc/COOH orthogonal protection, this building block is routinely employed in parallel solid‑phase synthesis (SPPS) and diversity‑oriented synthesis (DOS) to generate libraries of amides, esters, and amines. It supports hit‑to‑lead campaigns requiring rapid variation of the linking region.
3. Research & Development Applications
Target Validation via Chemical Probes
Researchers conjugate this linker to bioactive warheads (e.g., kinase inhibitors, GPCR ligands) to create chemical probes with an optional handle for affinity pulldown or fluorescence labeling. The Boc‑protected amine provides a convenient site for biotin or fluorophore attachment after uncapping, enabling target engagement and cellular localization studies.
Development of Dimeric and Multivalent Agents
The dual functionality allows the assembly of homodimers or heterodimers by coupling two different pharmacophores through the same linker backbone. This approach is used to investigate bivalent binding modes in receptors, transporters, and protein‑protein interactions.
4. Handling & Storage
Storage Conditions
Store as supplied in tightly sealed, dry containers at –20 °C, protected from light and moisture. The compound is stable under recommended conditions. Stock solutions in DMSO or DMF should be aliquoted and stored at –80 °C for long‑term use; avoid repeated freeze‑thaw cycles.
Intended Use
This compound is intended for laboratory research, chemical development, and preclinical studies only. It is not for human therapeutic, diagnostic, or food use without appropriate regulatory approval.
Summary
The value of Benzenepropanoic acid, 4-[[[(1,1-dimethylethoxy)carbonyl]amino]methyl]-α,α-dimethyl- lies in its unique combination of a Boc‑protected aminomethylbenzyl group and a sterically hindered α,α‑dimethylpropanoic acid, offering orthogonal reactivity, enhanced enzymatic stability, and predictable conjugation chemistry. These properties make it an indispensable building block for PROTACs, ADCs, peptide‑drug conjugates, and chemical probe development. Its reliable purity, defined structure, and versatile functionality support high‑throughput library synthesis, linker optimization, and translational research in targeted therapeutics.
For more information, please contact: selina@coreychem.com
