L-Azetidine-2-carboxylic acid is a non-proteinogenic amino acid featuring a constrained azetidine ring with a carboxylic acid at the 2-position and an amino functionality on the ring, classifying it as a cyclic amino acid analog. The molecule bears a primary amino group and a carboxyl group, with stereochemistry indicated by the "L" designation, and its ring-constrained side-chain geometry differs from open-chain amino acids while maintaining an amino acid-like connectivity for peptide chemistry. L-Azetidine-2-carboxylic acid is used as a substrate or building block in chemical biology and peptide-related studies where incorporation of a cyclic, conformationally restricted amino acid analog supports structure-activity comparisons and labeling or analytical method development.
CAT No: CP20301
CAS No:2133-34-8
Synonyms/Alias:(S)-Azetidine-2-carboxylicacid;L-Azetidine-2-carboxylicacid;2133-34-8;(S)-(-)-2-Azetidinecarboxylicacid;(2S)-azetidine-2-carboxylicacid;Azetidyl-2-carboxylicacid;(S)-2-Azetidinecarboxylicacid;L-Azetidine2-carboxylicacid;2-Azetidinecarboxylicacid,L-;Azetidine-2-carboxylicacid,L-;2-Azetidinecarboxylicacid,(S)-;UNII-5GZ3E0L9ZU;(S)-(-)-Azetidine-2-carboxylicacid;ST059592;CHEBI:6198;AcideL-azetidine-2-carboxylic;CHEMBL1165239;HSDB3465;IADUEWIQBXOCDZ-VKHMYHEASA-N;EINECS218-362-5;Azetidinecarboxylicacid;L-Trimethyleneimine-2-carboxylicAcid;(L)-AZETIDINE-2-CARBOXYLICACID;AcideL-azetidine-2-carboxylic[French];(2S)azetidine-2-carboxylicacid
L-Azetidine-2-carboxylic acid is a cyclic, conformationally constrained amino acid analog featuring an azetidine ring with a carboxylic acid at the 2-position. The molecule presents a chiral center at C-2 (L-configuration) and a secondary amine embedded within the strained four-membered heterocycle, giving distinct reactivity compared with acyclic amino acids. The carboxylic acid can be converted to activated esters, amides, or protected derivatives, while the ring nitrogen can be selectively protected or functionalized to tune chemoselectivity during synthesis. As an amino acid-based intermediate, L-azetidine-2-carboxylic acid can participate in peptide coupling chemistry and downstream scaffold elaboration where constrained geometry and heterocycle stability are desired.
1. Peptide Synthesis
L-Azetidine-2-carboxylic acid is applied in peptide building and peptide analog construction where azetidine ring constraints influence backbone conformation and protease/peptidase recognition. The carboxyl group enables C-terminal activation for amide bond formation, while the ring nitrogen can be protected to control N-chemistry during stepwise peptide synthesis. Side-chain-free cyclic structure supports incorporation as a single residue analog in short peptides, enabling peptide coupling strategies compatible with protected amino acid synthesis workflows. Downstream deprotection and selective functional group transformations can generate azetidine-containing peptide fragments for structure-activity relationship studies and method development in peptide chemistry.
2. Chemical Biology
L-Azetidine-2-carboxylic acid is used as a chemical biology reagent and biochemical research intermediate to probe amino acid recognition, transport, and enzyme substrate specificity involving constrained amino acid motifs. The L-stereochemistry at the 2-carboxyl-bearing carbon can be leveraged to assess stereochemical requirements in receptor or enzyme binding assays, while the azetidine nitrogen and carboxyl functionality provide handles for derivatization. Conversion to protected amino acid derivatives or activated carboxylates can support labeling workflows, affinity probe synthesis, or incorporation into peptidomimetic constructs used to interrogate biomolecular interactions. The resulting azetidine-containing analogs can serve as tools for studying structure-function relationships in amino acid-processing pathways.
3. Chiral Amino Acid Intermediate
L-Azetidine-2-carboxylic acid functions as a chiral azetidine-containing building block for stereoselective synthesis of constrained amines and amino acid derivatives. The defined L-configuration provides a stereochemical anchor that can be carried through protection, activation, and coupling sequences to produce enantiopure intermediates for fine chemical synthesis. The carboxylic acid can be transformed into esters or amides to enable downstream functional group interconversions, while N-protection strategies can modulate reactivity of the ring nitrogen during multistep routes. The compound's constrained heterocycle can also be retained as a structural element in chiral scaffolds used for molecular design and synthetic methodology development.
4. Peptidomimetics Development
L-Azetidine-2-carboxylic acid is suitable for peptidomimetic construction where a cyclic amino acid residue replaces flexible backbone segments to tune conformational preference. The azetidine ring introduces strain and defined geometry that can affect hydrogen-bonding patterns and local sterics around the amide linkage formed from the carboxyl group. The amino acid framework supports conversion into N-protected derivatives and activated C-terminal forms, facilitating incorporation into larger peptidomimetic libraries via standard peptide coupling chemistry. Downstream derivatization of the carboxyl-derived functionality enables generation of analog series for structure-activity relationship studies and medicinal chemistry lead optimization.
5. Pharmaceutical Manufacturing
L-Azetidine-2-carboxylic acid is relevant to pharmaceutical intermediate preparation for manufacturing routes that require incorporation of constrained amino acid motifs into drug-like scaffolds. The presence of a carboxylic acid and a ring nitrogen supports conversion into protected intermediates that can be handled under controlled chemoselectivity during scale-up, including esterification, amide formation, and N-protection/deprotection sequences. The stereodefined L-center allows consistent stereochemical outcomes across synthetic batches when used as a chiral building block. The azetidine residue can serve as a repeatable unit in the synthesis of peptide-like intermediates and constrained heterocycle-containing compounds used in chemical manufacturing workflows.
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