DL-Cyclopropylalanine is a non-proteinogenic amino acid derivative in which the side chain is a cyclopropyl substituent attached to the α-carbon, giving a constrained, hydrophobic ring-bearing structure. The molecule contains a free amino group and a free carboxyl group, and the "DL-" designation indicates a racemic mixture of stereoisomers at the α-carbon, which can influence how the compound is incorporated or recognized in peptide-like structures. It is used as a building block for peptide and peptidomimetic synthesis and for structure-activity or conformational studies where cyclopropyl side-chain geometry and lipophilicity are varied across analogues.
CAT No: CP21303
DL-Cyclopropylalanine is a non-proteinogenic amino acid featuring a cyclopropyl side chain attached to the stereogenic alpha carbon, with an amino group and a carboxylic acid functionality that can be converted into peptide-compatible derivatives. The DL designation indicates a racemic mixture at the alpha stereocenter, enabling use in stereochemical screening, racemate-based SAR workflows, and intermediate preparation where later resolution or stereoselective steps are planned. The cyclopropyl ring contributes a compact, conformationally constrained hydrophobic motif that can participate in structure-property studies and can be carried through peptide coupling or further side-chain functionalization. The amino and carboxyl groups support standard protection-group strategies for protected amino acid synthesis and downstream conversion into amide-linked products, including peptide building blocks and chiral intermediates for fine chemical manufacturing.
1. Peptide Synthesis
DL-Cyclopropylalanine is applied in peptide synthesis as an amino acid building block for generating amide linkages via standard coupling chemistries after conversion to an activated or protected form. The free amino and carboxyl groups enable formation of N-protected derivatives and C-terminal functionalization, supporting stepwise assembly of linear peptides and peptide fragments. The cyclopropyl side chain can be retained through coupling to introduce a conformationally constrained hydrophobic residue for peptide analog construction. Racemic incorporation from the DL material can be used in parallel synthesis to compare sequence effects before committing to stereochemically enriched analogs.
2. Peptidomimetics And SAR
DL-Cyclopropylalanine is used in peptidomimetic and SAR studies to install a cyclopropyl-bearing residue that modulates sterics, hydrophobicity, and local conformational preferences in bioactive scaffolds. The amino acid backbone supports conversion into protected amino acid intermediates suitable for amide bond formation, while the cyclopropyl ring serves as a stable side-chain motif that can be carried into constrained analogs. Racemic availability can support early-stage structure-activity relationship studies where stereochemical dependence is assessed by later resolution or stereoselective synthesis. Downstream derivatization can include N-alkylation, side-chain oxidation or functional group interconversions when compatible with the protection strategy used for peptide coupling.
3. Chiral Resolution Intermediates
DL-Cyclopropylalanine is employed as a chiral synthesis feedstock in workflows that generate enantiopure cyclopropylalanine derivatives through resolution or stereoselective transformations. The presence of a single stereogenic center at the alpha carbon makes the compound directly relevant to forming diastereomeric salts or intermediates that can be separated to yield defined stereochemistry. The amino acid functional groups support conversion to protected amino acid derivatives that can survive resolution steps and later be used for peptide coupling or further functionalization. The cyclopropyl side chain remains intact during stereochemical operations, enabling preparation of chiral amino acid intermediates for downstream medicinal chemistry and process-oriented fine chemical synthesis.
4. Amino Acid Derivatization
DL-Cyclopropylalanine is applied in amino acid derivatization chemistry to access esters, amides, and N-protected derivatives used as intermediates across synthetic organic chemistry. The carboxylic acid can be transformed into activated esters or protected acid forms, while the amino group can be protected to control chemoselectivity during multi-step syntheses. The cyclopropyl side chain tolerates many protection-group manipulations, supporting its use in building blocks for heteroatom-containing analogs and functionalized peptide fragments. Resulting derivatives can be used for subsequent coupling, conjugation chemistry, or as standardized inputs to automated synthesis platforms that require defined amino acid reactivity profiles.
5. Analytical Standards Development
DL-Cyclopropylalanine is suitable for analytical research and method development where racemate-aware standards are required for amino acid profiling, chiral analysis, or impurity characterization. The defined amino acid structure with a cyclopropyl side chain enables targeted detection in chromatographic workflows after derivatization, including formation of detectable derivatives from the amino and carboxyl functionalities. The DL stereochemical nature supports calibration for racemic mixtures and can be paired with enantiopure reference materials to evaluate stereochemical separation performance. Downstream use includes preparation of labeled or derivatized analogs for method validation in biochemical research intermediate qualification and synthetic process monitoring.
6. Pharmaceutical Intermediate Preparation
DL-Cyclopropylalanine is used as an industrial and process chemistry intermediate for manufacturing routes that require amino acid-based building blocks for peptide-like structures and constrained side-chain motifs. The amino acid functionality supports conversion into protected amino acid derivatives compatible with scalable peptide coupling strategies, including N-protection and C-terminal activation approaches that preserve stereochemical integrity when later resolved. The cyclopropyl residue can be carried into amide-linked intermediates used for fine chemical synthesis, including peptidomimetic fragments and platform molecules for further elaboration. Industrial relevance is supported by the straightforward transformation of the amino acid into protected or activated forms that integrate into downstream synthetic operations for specialty chemical production.
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