DL-azetidine-2-carboxylic acid is a non-proteinogenic amino acid analogue featuring a four-membered azetidine ring with a carboxylic acid at the 2-position and an amino group on the ring, classifying it as a cyclic amino acid. The "DL" designation indicates a racemic mixture of stereoisomers at the stereogenic center(s) associated with the azetidine-2-carboxyl framework, and the molecule bears both amino and carboxyl functional groups that can be present as free amino acid forms or converted into salts or protected derivatives for controlled reactivity. In research and peptide chemistry, it is used as a structural probe and building block for incorporating cyclic, conformationally constrained residues into peptide analogues and for studying structure-activity relationships or binding/recognition effects in chemical biology assays.
CAT No: CP20303
DL-azetidine-2-carboxylic acid is a cyclic, constrained amino acid analog featuring an azetidine ring with a carboxylic acid at the 2-position, providing a stereochemically defined, ring-locked scaffold while existing as a racemic mixture (DL). The molecule presents a primary carboxylic acid functionality and a secondary amine embedded in the azetidine framework, enabling acid-base behavior and controlled derivatization into protected amino acid intermediates. Ring strain and conformational restriction can influence reactivity and coupling behavior compared with acyclic amino acids, while the lack of a side-chain substituent beyond the ring makes it a clean structural handle for building azetidine-containing peptide analogs. As a chiral synthetic intermediate precursor in amino acid chemistry, DL-azetidine-2-carboxylic acid can be transformed into N-protected forms, activated carboxyl derivatives, and downstream functionalized derivatives for peptide construction and structure-focused molecular design.
1. Peptide Synthesis
DL-azetidine-2-carboxylic acid supports peptide building-block workflows where incorporation of a cyclic azetidine residue is used to probe backbone constraints and amide-bond formation outcomes. The carboxylic acid can be converted to activated esters or coupling-ready derivatives, while N-protection strategies can mask the ring nitrogen to enable selective peptide coupling at the carboxylate. Racemic availability allows parallel synthesis of azetidine-containing peptide libraries, with stereochemical effects addressed downstream via chiral resolution or stereodefined analog synthesis. The resulting azetidine-containing peptides and peptidomimetics serve as research-grade substrates for studying conformational preferences and sequence-dependent stability in peptide science.
2. Peptidomimetics And SAR Studies
DL-azetidine-2-carboxylic acid is applicable to structure-activity relationship studies that require incorporation of a constrained amino acid mimic to modulate hydrogen bonding patterns and conformational sampling. The ring-locked azetidine scaffold provides a defined spatial relationship between the amide-forming nitrogen and the carboxyl-derived linkage, enabling SAR campaigns to evaluate how backbone restriction affects binding-site complementarity. Derivatization into N-protected amino acid derivatives and subsequent peptide assembly can generate azetidine-bearing analogs for systematic comparison across series. Downstream use includes the preparation of peptidomimetic fragments and analog panels suitable for medicinal chemistry screening and mechanistic biochemical characterization.
3. Chiral Synthesis Intermediate
DL-azetidine-2-carboxylic acid functions as a starting chiral amino acid intermediate for routes that address stereochemical control through resolution, stereoselective transformations, or conversion to chiral auxiliaries. The racemic nature provides feedstock for processes that separate enantiomers or convert the amino acid into diastereomeric derivatives, after which deprotection yields stereodefined azetidine-2-carboxylic acid analogs. The azetidine ring nitrogen and carboxyl group can be orthogonally protected to manage selective functional group interconversions during synthetic sequence design. The resulting stereochemically defined intermediates can then be used for constructing azetidine-containing peptide building blocks and other chiral, ring-constrained scaffolds.
4. Chemical Biology Probes
DL-azetidine-2-carboxylic acid can be employed in chemical biology research where azetidine-containing residues are introduced to tune peptide stability, protease resistance, or conformational behavior of biomolecule ligands. The carboxylic acid and ring nitrogen enable preparation of protected amino acid derivatives that can be incorporated into peptides for labeling, affinity probes, or substrate analogs used to interrogate biomolecular interactions. Functional group transformations of the carboxyl moiety into activated intermediates support conjugation workflows that attach the azetidine residue to larger molecular frameworks. Downstream applications include generation of constrained peptide probes and biomolecule-modified constructs for studying recognition events and processing pathways in biochemical assays.
5. Pharmaceutical Intermediate Preparation
DL-azetidine-2-carboxylic acid is suitable for pharmaceutical intermediate preparation in fine chemical synthesis programs that require azetidine-containing building blocks for medicinal chemistry and process development. The amino acid functionality can be routed through N-protection and carboxyl activation steps to produce coupling-ready intermediates compatible with peptide-like bond formation strategies used in drug candidate synthesis. Conformational constraint from the azetidine ring can be leveraged to access structurally defined fragments used in iterative synthesis of analogs and process intermediates. Industrially relevant downstream formation includes preparation of protected azetidine amino acid derivatives and peptide coupling intermediates that can be scaled as part of specialty chemical production and chemical manufacturing supply chains.
6. Analytical Standards in Peptide Research
DL-azetidine-2-carboxylic acid supports analytical research by serving as a reference material for method development and impurity profiling in azetidine-containing peptide chemistry. The defined molecular framework, with a carboxylic acid and azetidine ring, enables targeted detection and calibration when monitoring protected amino acid derivatives, coupling intermediates, or deprotected residues. Derivatization into N-protected or esterified forms can broaden compatibility with chromatographic or spectrometric workflows used to quantify incorporation efficiency and stereochemical composition. Downstream utility includes preparation of analytical standards for peptide synthesis characterization, enabling consistent monitoring of azetidine residue presence across synthetic batches and research studies.
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