D-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 framework, classifying it as a cyclic, constrained amino acid. The molecule is specified as the D stereoisomer and presents a primary amino functionality and a carboxyl group that can exist in zwitterionic forms, while the ring strain and restricted geometry influence side-chain-like conformational behavior relative to open-chain amino acids. It is used in peptide and peptidomimetic synthesis and structure-activity studies as a conformationally constrained building block, and it can also serve as a substrate or reference compound in analytical method development for amino acid analogue detection.
CAT No: CP20302
D-azetidine-2-carboxylic acid is a chiral, non-proteinogenic amino acid analog featuring a strained four-membered azetidine ring with a carboxylic acid at the 2-position, providing an amino acid-like primary functional handle for peptide chemistry. The stereogenic center at C-2 (D-configuration) governs conformational preferences and can influence binding-mode outcomes in peptidomimetics and receptor-facing scaffolds. The molecule's carboxylic acid and ring nitrogen enable predictable protection-group strategies, including conversion to N-protected forms and activation of the acid for amide bond formation. Reactivity as an amino acid building block supports downstream derivatization into protected amino acid intermediates, coupling-ready derivatives, and chiral fragments for synthetic methodology and structure-function studies.
1. Peptide Synthesis
D-azetidine-2-carboxylic acid is employed in peptide synthesis as a chiral, amino acid-like building block that can be incorporated into peptide chains through standard carboxyl activation and amide coupling chemistry. The azetidine ring nitrogen and the 2-carboxyl group support orthogonal protection approaches, enabling controlled N-protection while leaving the carboxyl functionality available for coupling. D-configuration can be retained during derivative preparation and used to construct stereochemically defined peptide analogs that probe how ring strain and stereochemistry affect backbone recognition. The resulting azetidine-containing peptides serve as research-grade substrates for studying peptide conformation, binding interactions, and SAR-driven scaffold refinement.
2. Peptidomimetics And SAR
D-azetidine-2-carboxylic acid is suitable for peptidomimetic construction in medicinal chemistry and structure-activity relationship studies where a constrained azetidine motif can modulate spatial arrangement of functional groups. The rigid ring and stereogenic center can be leveraged to tune side-chain geometry relative to the amide backbone, supporting design of analog series that compare stereochemical and conformational effects. Carboxylic acid activation and N-protection strategies facilitate rapid generation of amide-linked analogs, including C-terminal modifications and incorporation into larger scaffold fragments. Downstream derivatives produced from this chiral amino acid analog can be used to map structure-function relationships for binding-site hypotheses and to guide iterative molecular design.
3. Chiral Building Block Synthesis
D-azetidine-2-carboxylic acid functions as a chiral amino acid intermediate for asymmetric and stereocontrolled synthesis of azetidine-containing fine chemicals. The D-stereocenter and amino acid functional pattern support conversion into coupling-ready intermediates such as N-protected derivatives and activated carboxylic acid forms, which can then be used to assemble larger chiral frameworks. The azetidine ring can participate in subsequent functional group transformations while maintaining stereochemical integrity when protection and activation steps are chosen appropriately. The compound therefore serves as a practical chiral fragment for producing stereodefined intermediates used in synthetic organic chemistry and downstream heterocycle- and peptidomimetic-related manufacturing routes.
4. Chemical Biology Probes
D-azetidine-2-carboxylic acid is applied in chemical biology research as a non-natural amino acid handle for building labeled or reactive peptide-like probes. The amino acid-like carboxyl group supports conjugation strategies through amide formation, while the ring nitrogen can be protected to enable selective downstream functionalization without premature side reactions. D-configuration can be used to control stereochemical presentation of the azetidine motif in probe constructs, which can affect recognition by enzymes, binding proteins, or assay reagents. The resulting azetidine-containing biomolecular tools can be employed to interrogate substrate preferences, molecular recognition, and mechanism-relevant interactions in biochemical studies.
5. Pharmaceutical Intermediate Preparation
D-azetidine-2-carboxylic acid is relevant to pharmaceutical intermediate preparation where azetidine-containing building blocks are incorporated into synthetic sequences for drug-like candidates and process development materials. The carboxylic acid and amino functionality enable conversion into protected amino acid derivatives and coupling-ready intermediates that integrate into peptide-like or amide-rich structures. Protection-group selection can support chemoselective steps, including temporary N-protection and controlled deprotection to match the order of bond-forming events in a manufacturing route. The compound's chiral nature supports stereochemically defined intermediate supply for consistent downstream synthesis of complex molecules used in applied chemical manufacturing workflows.
6. Industrial Fine Chemical Synthesis
D-azetidine-2-carboxylic acid can be utilized in industrial fine chemical synthesis as a chiral, ring-constrained amino acid analog for producing azetidine-bearing scaffold intermediates. The stable amino acid functional motif allows scalable derivatization into N-protected and activated carboxyl derivatives that are compatible with industrially practiced coupling chemistries for amide bond construction. The azetidine ring's structural constraint can improve synthetic design by providing a defined three-dimensional element that persists into downstream products, including peptidomimetics and amide-rich intermediates. The compound thereby supports specialty chemical production where chiral building blocks are required for stereodefined molecular assembly and downstream functional material or bioactive-mimetic precursor generation.
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