DL-Cyclopropylglycine is a cyclopropyl-substituted amino acid derivative in which the side chain bears a cyclopropyl ring, classifying it as a nonstandard, proteinogenic-analog amino acid for peptide and structure-activity studies. The molecule contains both an amino group and a carboxyl group on the α-carbon and is supplied as the DL racemate, with the cyclopropyl side chain providing a conformationally constrained hydrophobic functionality. In synthetic chemistry and chemical biology workflows, it is employed as a substrate building block for preparing modified peptides and amino acid derivatives, including labeling or SAR investigations where restricted side-chain geometry is used to probe binding or conformational effects.
CAT No: CP21203
DL-Cyclopropylglycine is a non-proteinogenic amino acid derivative featuring a cyclopropyl-substituted side chain attached to the α-amino acid backbone, existing as a racemic mixture of stereocenters (DL). The molecule contains a primary amine and a carboxylic acid functionality, which can be selectively protected as N-protected amino acid derivatives and converted into activated coupling forms for peptide chemistry. The cyclopropyl group introduces conformational constraint and distinctive steric and electronic properties that can influence amide bond geometry, conformational preferences, and metabolic stability trends in peptidomimetic scaffolds. As an amino acid-based intermediate, DL-Cyclopropylglycine can be used to access both protected building blocks and downstream cyclopropyl-containing analogs through standard amino acid derivatization and stereochemical control strategies.
1. Peptide Synthesis
DL-Cyclopropylglycine is applied in peptide synthesis and peptidomimetic construction where a cyclopropyl-bearing side chain is used to modulate backbone conformation and side-chain sterics. The α-amino and α-carboxyl groups enable formation of amide bonds after conversion to N-protected forms and carboxyl-activated coupling derivatives, supporting compatibility with common peptide coupling chemistries. Racemic (DL) material can be employed for generating libraries of cyclopropyl-containing peptides when stereochemical uniformity is not required, while downstream resolution or asymmetric derivatization strategies can be used when a single enantiomer is desired. Cyclopropylglycine-containing peptides and analogs can then serve as research reagents for scaffold comparison in structure-activity relationship studies and as intermediates toward more complex peptide-based molecules.
2. Amino Acid Derivatization
DL-Cyclopropylglycine is used as an amino acid derivatization feedstock for producing protected amino acid derivatives, amino acid esters, and activated intermediates for fine chemical synthesis. The presence of an α-carboxylic acid allows esterification or conversion to acid chlorides, anhydrides, or coupling-ready species, while the primary amine supports N-protection strategies such as Boc- or Fmoc-type protection to control chemoselectivity during multistep synthesis. The cyclopropyl side chain can tolerate many standard protection/deprotection conditions and can be carried through peptide coupling sequences without introducing additional reactive functionality. Resulting derivatives can function as chiral synthetic intermediates after enantiomer separation or as stable building blocks for subsequent side-chain functionalization and analog generation.
3. Chiral Building Block Development
DL-Cyclopropylglycine is relevant to chiral synthesis workflows where racemic amino acid material is processed into enantiomerically enriched building blocks for stereochemically defined peptide analogs. The α-stereocenter can be targeted through resolution approaches or via formation of diastereomeric derivatives, enabling access to single-enantiomer cyclopropylglycine for stereocontrolled coupling and downstream SAR studies. N-protected amino acid derivatives derived from the resolved enantiomer can be integrated into peptide assembly while maintaining stereochemical integrity at the α-carbon. Cyclopropylglycine-based chiral intermediates can then support medicinal chemistry campaigns focused on stereochemical effects on binding-site recognition and conformational behavior, while also serving as process chemistry intermediates for scalable asymmetric routes.
4. Chemical Biology And SAR Studies
DL-Cyclopropylglycine is employed in chemical biology and SAR studies to generate cyclopropyl-containing amino acid substitutions that probe how constrained side chains affect molecular recognition. The amino acid backbone supports incorporation into peptide mimics, while the cyclopropyl group provides a compact, conformationally restricted motif that can alter local geometry around amide linkages. N- and C-terminal functionalization strategies, including orthogonal protection of the amine and controlled activation of the carboxyl group, enable systematic construction of analog series for comparative studies. Cyclopropylglycine-containing compounds can be used as biochemical research intermediates for mapping structure-function relationships in receptor-binding assays, enzyme substrate analog investigations, and fragment-to-lead optimization programs.
5. Pharmaceutical Manufacturing Intermediates
DL-Cyclopropylglycine is suitable for pharmaceutical manufacturing and specialty chemical production as a defined amino acid starting material for producing peptide-like intermediates and non-proteinogenic building blocks. The functional groups permit conversion into protected amino acid derivatives and coupling-ready forms that align with industrial peptide synthesis logistics, including controlled deprotection steps to reveal reactive termini at the correct stage. The cyclopropyl side chain provides a chemically stable handle for incorporating constrained motifs into drug-like scaffolds without requiring additional functional-group interconversions. Downstream manufacturing utility includes preparation of cyclopropylglycine-containing fragments for further assembly, as well as generation of standardized intermediates for process development and scale-up of peptidomimetic synthesis routes.
6. Analytical Research Standards
DL-Cyclopropylglycine is used in analytical research for method development and reference standard preparation involving amino acid derivatization and chiral or achiral chromatographic characterization. The combination of a primary amine and carboxylic acid enables derivatization schemes that support detection by common analytical platforms, while the cyclopropyl side chain provides a distinct structural signature for separation and identification. Racemic composition supports calibration for DL-specific workflows, and enantiomeric derivatives can be prepared when stereochemical resolution is required for quality control of cyclopropylglycine-containing intermediates. Cyclopropylglycine standards and derivatives can therefore serve in characterization of peptide building blocks, monitoring of synthesis progress, and verification of stereochemical outcomes in amino acid intermediate production.
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