2-Azetidinecarboxylic acid, 3,3-dimethyl-, (2S)-

2-Azetidinecarboxylic acid, 3,3-dimethyl-, (2S)- is a sterically hindered, non-natural α-amino acid that serves as a conformationally constrained building block for peptide and peptidomimetic design. The four-membered azetidine ring, smaller than the five-membered ring of proline analogs, significantly increases backbone rigidity, making 2-Azetidinecarboxylic acid, 3,3-dimethyl-, (2S)- highly valuable for peptide engineering applications. As a versatile chiral scaffold, 2-Azetidinecarboxylic acid, 3,3-dimethyl-, (2S)- enables researchers to explore novel chemical space beyond the 20 canonical amino acids. Incorporating 2-Azetidinecarboxylic acid, 3,3-dimethyl-, (2S)- into peptide sequences restricts conformational flexibility and has been shown to enhance binding affinity to targets such as G-protein-coupled receptors (GPCRs).

Product Parameters

Why Cosperpharm?

When your peptide engineering or drug discovery program demands high-quality, conformationally constrained building blocks, Cosperpharm delivers 2-Azetidinecarboxylic acid, 3,3-dimethyl-, (2S)- with the purity, documentation, and service that researchers and pharmaceutical developers require.

Purity that ensures peptide integrity. The azetidine scaffold is sensitive to racemization and impurities that can compromise the conformational integrity of your peptides. Our analytical release protocol for 2-Azetidinecarboxylic acid, 3,3-dimethyl-, (2S)- includes HPLC purity verification (≥97%), appearance verification, and full spectroscopic confirmation — because the biological activity of your constrained peptide depends on the quality of this building block.

Expertise in non-natural amino acids. Cosperpharm understands the unique challenges of working with sterically hindered, non-natural amino acids. Our team can advise on Fmoc protection conditions, coupling strategies, and incorporation of 2-Azetidinecarboxylic acid, 3,3-dimethyl-, (2S)- into peptide sequences — because we know that these specialized building blocks require specialized knowledge.

Documentation that supports your research. Every shipment of 2-Azetidinecarboxylic acid, 3,3-dimethyl-, (2S)- includes a Certificate of Analysis (COA) with batch-specific data, a Material Safety Data Sheet (SDS), and customs documentation for international delivery. Custom quality agreements are available upon request.

Flexible supply for all research stages. Cosperpharm supplies 2-Azetidinecarboxylic acid, 3,3-dimethyl-, (2S)- from milligram-scale for medicinal chemistry screening to gram-scale for process development and preclinical studies. R&D samples ship within 5–7 business days.

Global reach with transparent pricing. Cosperpharm ships worldwide. Volume discounts apply, and we communicate lead times upfront — no hidden fees, no unexpected delays.

Product Advantages

 Rigid, Conformationally Constrained Azetidine Scaffold

2-Azetidinecarboxylic acid, 3,3-dimethyl-, (2S)- features a four-membered azetidine ring that imposes significant steric constraints, reducing ring puckering and stabilizing specific conformations. The smaller ring size compared to five-membered proline analogs increases backbone rigidity, making it highly valuable for peptide engineering. Incorporating this residue into peptides restricts backbone flexibility, enhancing binding affinity to targets such as GPCRs.

 Non-Natural Amino Acid for Expanding Chemical Space

As a non-proteinogenic, sterically hindered α-amino acid, 2-Azetidinecarboxylic acid, 3,3-dimethyl-, (2S)- enables exploration beyond the 20 canonical amino acids. Research groups have successfully incorporated derivatives of this compound into various peptide frameworks, demonstrating their utility as replacements for natural amino acids in bioactive sequences.

 Versatile Precursor for Fmoc-Protected Derivatives

2-Azetidinecarboxylic acid, 3,3-dimethyl-, (2S)- is the immediate precursor to Fmoc-(S)-3,3-dimethylazetidine-2-carboxylic acid (CAS 2231665-66-8). The Fmoc-protected derivative is compatible with standard SPPS, facilitating the assembly of constrained peptide motifs.

 Enhanced Binding Affinity Demonstrated

Peptides containing 2-Azetidinecarboxylic acid, 3,3-dimethyl-, (2S)- residues have demonstrated significantly improved pharmacological properties. For example, azetidine-containing peptides showed 10-fold higher affinity for serotonin receptors compared to proline-containing analogs. Derivatives have also demonstrated anticancer activity (IC₅₀ = 12 µM in HeLa cells) and enzyme inhibition (Kᵢ = 8 nM for carbonic anhydrase IX).

 Broad Utility in Drug Discovery

2-Azetidinecarboxylic acid, 3,3-dimethyl-, (2S)- is extensively utilized in structural biology and protein engineering to elucidate protein folding mechanisms and engineer proteins with desired properties. Its derivatives are used in the synthesis of anticancer peptides, enzyme inhibitors, and other bioactive molecules.

 Storage Conditions

Shelf life: When stored under recommended conditions in a sealed, dry container protected from light, 2-Azetidinecarboxylic acid, 3,3-dimethyl-, (2S)- maintains stability for extended periods.

Handling precautions: Use in a fume hood. Wear appropriate personal protective equipment — lab coat, safety goggles, and chemical-resistant gloves. Avoid generating dust. After handling, wash hands thoroughly. The compound is classified with hazard statements H302 (Harmful if swallowed), H315 (Causes skin irritation), H319 (Causes serious eye irritation), and H335 (May cause respiratory irritation). Signal word: Warning.

 Contact Us

Ready to incorporate 2-Azetidinecarboxylic acid, 3,3-dimethyl-, (2S)- into your peptide engineering or drug discovery program? Cosperpharm provides the quality, expertise, and support you need. Reach out to our team today — we're here to help you overcome the challenges of incorporating sterically hindered, non-natural amino acids into your next-generation peptide therapeutics.