D-Cyclopropylglycine is a non-proteinogenic amino acid featuring a glycine backbone bearing a cyclopropyl side chain, with stereochemistry specified as the D-enantiomer and with both an amino group and a carboxyl group present in the free amino acid form. The cyclopropyl substituent imparts a constrained, hydrophobic, and sterically defined side-chain environment while the α-amino and α-carboxyl functionalities enable salt formation and standard amino-acid derivatization chemistry. D-Cyclopropylglycine is used in peptide and peptidomimetic synthesis and in structure-activity or conformational studies where incorporation of a cyclopropyl-bearing residue can modulate backbone/side-chain geometry and physicochemical properties.
CAT No: CP21202
D-Cyclopropylglycine is a D-configured amino acid featuring a cyclopropyl-substituted side chain attached to a stereogenic alpha carbon, making it a chiral amino acid building block for stereocontrolled synthesis. The molecule presents a free primary amine and a carboxylic acid functional group in its typical amino acid form, enabling standard peptide coupling chemistry and salt formation for handling. The cyclopropyl ring contributes a compact, conformationally constrained hydrophobic motif that can influence backbone and side-chain conformations in peptidomimetics and enzyme-binding studies. The combination of a defined D stereocenter and a reactive amino acid functional set also supports downstream derivatization to protected amino acid derivatives or activated intermediates used in peptide construction and synthetic organic chemistry.
1. Peptide Synthesis
D-Cyclopropylglycine is applied in peptide synthesis where the D stereochemistry at the alpha carbon enables incorporation of a stereodefined residue into linear peptides and peptide fragments. The free carboxylic acid and amine functionality can be converted into peptide-compatible forms through protection and activation, supporting amide bond formation under common coupling strategies used for protected amino acids. The cyclopropyl side chain can be introduced as a constrained hydrophobic element to probe how sterics and conformational bias affect peptide folding and binding. Peptide building block preparation from D-Cyclopropylglycine supports the generation of D-amino acid containing analogs for structure-activity relationship studies and synthetic methodology development.
2. Peptidomimetics Development
D-Cyclopropylglycine is utilized in peptidomimetics and molecular scaffold design as a D-amino acid analog that introduces a cyclopropyl group without adding heteroatoms to the side chain. The stereogenic center and amino acid backbone allow controlled placement of the residue within peptide-like frameworks, while the cyclopropyl ring can modulate local steric profiles and conformational preferences. Side-chain hydrophobicity and ring strain may be leveraged during design of enzyme-binding inhibitors, receptor ligands, or protease-resistant peptide mimics where D-amino acid incorporation is used to tune metabolic stability and binding geometry. Downstream derivatization into protected amino acid derivatives or activated coupling partners enables systematic analog generation for medicinal chemistry research.
3. Chemical Biology Probes
D-Cyclopropylglycine is suitable for chemical biology research where the amino acid framework can be functionalized into labeling handles or conjugation-ready intermediates for biomolecule modification. The primary amine and carboxylic acid provide attachment points for installing orthogonal protecting groups, linkers, or reactive groups that can be used to build conjugates while preserving the D stereochemical identity. The cyclopropyl side chain can serve as a hydrophobic element to study molecular recognition in protein-ligand and enzyme-substrate contexts, including experiments that compare stereochemical effects on binding. The resulting D-cyclopropylglycine-derived derivatives can be employed as biochemical research intermediates for constructing probe libraries and evaluating structure-dependent interactions.
4. Process Chemistry Intermediate
D-Cyclopropylglycine is applied as a chiral amino acid intermediate in process chemistry and fine chemical synthesis where stereochemical integrity is maintained from upstream chiral feedstocks through downstream derivative formation. The presence of both amine and carboxylic acid functional groups enables conversion into protected amino acid derivatives, activated esters, or coupling-ready intermediates that fit into scalable peptide-manufacturing workflows. The cyclopropyl side chain can be carried through multiple synthetic steps without requiring additional functional group manipulations, supporting route design for producing D-amino acid containing building blocks. Industrial manufacturing relevance includes the preparation of stereodefined amino acid derivatives used to generate peptide analogs and peptidomimetic intermediates at chemical plant scale.
5. Analytical Standards
D-Cyclopropylglycine is used for analytical research as a stereochemically defined amino acid standard and reference material in method development for chiral separations and amino acid profiling. The D configuration and cyclopropyl side chain provide a distinguishable chemical signature that can support LC-MS or chromatographic workflows aimed at monitoring D-amino acid incorporation in peptide synthesis and degradation studies. The amino acid's functional groups enable derivatization into detectable derivatives compatible with common analytical detection schemes, supporting reproducible quantitation and identity confirmation. Analytical standard development using D-Cyclopropylglycine supports quality control for peptide building block preparation and downstream characterization of D-amino acid containing products.
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