L-Cyclopropylglycine is a proteinogenic amino acid analogue in which the side chain is a cyclopropyl substituent attached to the glycine backbone, giving a compact, conformationally constrained alkyl functionality. The molecule contains a free amino group and a free carboxyl group, and it is presented in the L stereochemical form as indicated by the product name. L-Cyclopropylglycine is used in peptide synthesis and structure-activity studies to introduce a cyclopropyl-bearing residue that can modulate local sterics and backbone/side-chain conformational preferences in synthetic peptides and related amino acid derivatives.
CAT No: CP21201
L-Cyclopropylglycine is an L-configured amino acid featuring a cyclopropyl-substituted side chain attached to the glycine backbone, yielding a compact, conformationally constrained motif that can influence peptide backbone dynamics and receptor/enzymatic recognition. The molecule contains a free amino group and a carboxylic acid functionality, enabling direct participation in peptide coupling chemistry as well as derivatization into protected amino acid derivatives or activated intermediates. The cyclopropyl ring contributes distinctive steric and electronic characteristics, which can be leveraged for chiral scaffold design, unnatural amino acid incorporation, and downstream transformation into substituted cyclopropyl-containing analogs. The amino acid's zwitterionic behavior and functional group reactivity make it suitable for controlled protection strategies, coupling-compatible activation, and conversion into research-grade intermediates for medicinal chemistry and process-oriented synthesis.
1. Peptide Synthesis
L-Cyclopropylglycine is used in peptide synthesis and peptide analog construction as an L-configured unnatural amino acid building block that can be incorporated at defined positions to probe how cyclopropyl constraints affect amide formation and conformational preferences. The amino acid's carboxyl group and amino group support standard peptide coupling workflows after conversion to a protected amino acid derivative, such as N-protection of the amine and, when needed, C-terminal activation of the acid. Side-chain cyclopropyl substitution can be retained through coupling and subsequent deprotection steps, enabling the preparation of cyclopropyl-containing peptides suitable for structure-activity relationship studies. Incorporation into short peptides and longer peptide scaffolds supports downstream generation of analog libraries and mechanistic studies of peptide recognition.
2. Chiral Building Block Development
L-Cyclopropylglycine is applied as a chiral amino acid intermediate for stereoselective synthesis of cyclopropyl-bearing fragments used in chiral molecular design and asymmetric route planning. The L-stereocenter and the functional amino acid termini enable conversion into protected forms that maintain stereochemical integrity during N-alkylation, esterification, or acid activation. The cyclopropyl side chain can serve as a stereochemically informative substituent for fragment-based molecular design, where conformational restriction may tune binding-site fit and physicochemical properties. Downstream derivatization can generate substituted cyclopropyl glycine analogs and related heteroatom-functionalized variants used in medicinal chemistry and applied synthetic methodology.
3. Amino Acid Derivatization
L-Cyclopropylglycine is utilized for amino acid derivatization workflows that produce coupling-ready intermediates and functionalized derivatives for synthetic organic chemistry and biochemical reagent preparation. The free amine and carboxylic acid can be transformed into N-protected amino acid derivatives, amino acid esters, or activated acid derivatives, supporting controlled peptide coupling chemistry and selective functional group transformations. Cyclopropyl stability under typical protection/deprotection conditions allows retention of the side-chain motif while enabling modifications at the termini, including formation of amides, carbamates, or other nitrogen-containing derivatives. Resulting products can function as intermediates for peptidomimetic construction, analytical standards, and scaffold diversification in process chemistry intermediate development.
4. Chemical Biology Probes
L-Cyclopropylglycine is employed in chemical biology research as an unnatural amino acid for probing enzyme selectivity, substrate recognition, and structure-function relationships in peptide- or protein-related systems. The amino acid's reactive termini support incorporation into labeled or modified peptide constructs, while the cyclopropyl side chain can act as a conformationally constrained substituent that perturbs local interactions without requiring large functional groups. N-terminal or side-chain-modified derivatives derived from L-Cyclopropylglycine can be used to generate biochemical research intermediates for studying binding-site tolerance and catalytic mechanism hypotheses. Downstream conjugation-compatible derivatives can also support preparation of probe molecules for molecular recognition studies and method development in biochemical assay design.
5. Pharmaceutical Manufacturing Intermediates
L-Cyclopropylglycine is relevant to pharmaceutical manufacturing and specialty chemical production as a defined chiral amino acid feedstock for producing protected amino acid intermediates and peptide-grade building blocks used in downstream active-ingredient synthesis. The presence of an L-configured amino acid backbone enables manufacturing-oriented conversion into N-protected forms and activated derivatives that are compatible with scalable peptide coupling and controlled deprotection sequences. The cyclopropyl side chain can be carried through intermediate steps to deliver consistent structural motifs in final peptide-like intermediates or peptidomimetic scaffolds. Industrial chemical utility arises from its role as a stereochemically specified precursor for fine chemical synthesis routes that require robust handling of amino and carboxyl functional groups.
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