H-L-Pra-OH is a free amino acid derivative featuring an L-configured amino acid backbone bearing a side chain characteristic of proline-related residues (Pra) and a terminal carboxylic acid, with the molecule presented in its unprotected, zwitterionic form in typical aqueous conditions. The structure contains a primary amino group and a carboxyl functional group, enabling standard acid-base behavior and participation in peptide-coupling chemistry, while the ring-constrained side-chain functionality associated with Pra provides a defined conformational bias relative to acyclic amino acids. H-L-Pra-OH is used as a substrate for peptide synthesis and as a defined building block for preparing amino acid and peptide analogues in chemical biology, structure-activity studies, and analytical method development where the stereochemically specified, free amino acid form is required.
CAT No: CP25643
CAS No:23235-01-0
Synonyms/Alias:L-PROPARGYLGLYCINE;23235-01-0;(S)-2-Aminopent-4-ynoic acid;(2s)-2-aminopent-4-ynoic acid;4-Pentynoic acid, 2-amino-, (2S)-;L-2-Propynylglycine;L-C-Propargylglycine;(S)-2-Propargylglycine;(S)-2-Amino-4-pentynoic acid;(S)-Propargylglycine;(2S)-2-amino-4-Pentynoic acid;(S)-alpha-propargylglycine;(S)-alpha.Propargylglycine;8R9U8RVT6V;MFCD00077855;4-Pentynoic acid, 2-amino-, (S)-;PROPARGYLGLYCINE, L-;CHEBI:43797;(2S)-2-azaniumylpent-4-ynoate;UNII-8R9U8RVT6V;DTXSID60941728;L-Proparglycine;L-Pra-OH;H-Gly(Propargyl)-OH;L-2-Amino-4-pentynoic acid;CHEMBL50483;SCHEMBL254259;(S)-2-Aminopent-4-ynoicacid;BDBM367672;L-Propargylglycine (H-L-Pra-OH);BBL101635;NSC823853;STL555431;AKOS005259648;AKOS006237180;AC-9947;CS-W006064;FP40143;HY-W006064;NSC-823853;AS-14794;L-C-Propargylglycine, >=99.0% (TLC);DB-002778;EN300-66130;C22138;Q27270926;US10227314, Compound (S)-2-aminopent-4-ynoic acid;812-854-9;Lph;
Chemical Name:L-Propargylglycine
H-L-Pra-OH is an amino acid derivative corresponding to L-proline bearing a praseolated side-chain motif (Pra) and presented as a free carboxylic acid, enabling it to function as a chiral amino acid building block in peptide and peptidomimetic synthesis. The structure contains an L-configured stereocenter at the proline-derived framework, a secondary amide-forming nitrogen within the proline ring, and a terminal carboxyl group for coupling chemistry. The side-chain functionality associated with Pra can participate in selective derivatization and downstream functional group installation, while the unprotected carboxylic acid supports formation of amide linkages under standard peptide coupling conditions. As a chiral amino acid intermediate, H-L-Pra-OH can be incorporated into synthetic sequences that require stereochemical fidelity and controlled reactivity of the amino and carboxyl functionalities.
1. Peptide Synthesis
H-L-Pra-OH is suitable for peptide building block preparation where the proline-based nitrogen and the free carboxyl group enable amide bond formation during stepwise peptide synthesis. The L stereochemistry supports stereodefined incorporation into peptide backbones, and the carboxylic acid functionality can be converted to activated intermediates or used in coupling strategies compatible with protected amino acid chemistry. The Pra side-chain motif can be retained for later functional group elaboration or can be temporarily protected to preserve orthogonality during chain assembly. Downstream, peptide analogs containing H-L-Pra-OH can be generated for backbone constraint studies, conformational tuning, and synthetic library construction.
2. Amino Acid Derivatization
H-L-Pra-OH is applicable to amino acid derivatization workflows that target the Pra side-chain for chemical modification while maintaining the proline-derived chiral core. The presence of a free carboxylic acid allows formation of esters, amides, or activated carboxyl derivatives that can be carried through multi-step syntheses before final deprotection or functional group interconversion. The secondary amine within the proline ring can be managed through protection/deprotection strategies to achieve selective side-chain transformations without cross-reactivity. Resulting derivatives can serve as intermediates for further medicinal chemistry exploration, chemical biology probes, or process-ready reagents for fine chemical synthesis.
3. Peptidomimetics Construction
H-L-Pra-OH can be employed in peptidomimetic construction where proline-like conformational restriction and the Pra side-chain provide handles for scaffold diversification. The chiral amino acid backbone supports stereochemically defined incorporation into non-natural peptide analogs, and the terminal carboxyl group can be used to generate amide-linked structures that mimic peptide geometry. Side-chain functionalization enabled by the Pra motif can support conversion into heteroatom-containing substituents, electrophile/nucleophile pairs, or constrained pharmacophore elements used in structure-activity relationship studies. Peptidomimetic products derived from H-L-Pra-OH can be used as research-grade molecular tools for evaluating binding mode hypotheses and conformational preferences.
4. Chemical Biology Probes
H-L-Pra-OH is suitable for chemical biology research where amino acid-based scaffolds are modified into labeling reagents or affinity tags through controlled functional group chemistry. The free carboxyl group supports conjugation strategies to biomolecule-reactive handles, while the proline-derived ring nitrogen can be protected to regulate chemoselectivity during probe assembly. The Pra side-chain motif can be leveraged to introduce reactive groups for coupling to nucleophiles on proteins or to incorporate reporter functionalities after orthogonal transformations. Resulting probe conjugates can be used to investigate biomolecular interactions, substrate recognition patterns, or conformational effects in peptide-mediated processes.
5. Pharmaceutical Intermediate Preparation
H-L-Pra-OH serves as a chiral amino acid intermediate for pharmaceutical intermediate preparation where stereodefined building blocks are required for downstream synthesis of non-natural peptidic motifs. The free carboxylic acid group supports conversion into protected acid forms, activated esters, or coupling-ready derivatives that integrate into larger synthetic routes under process chemistry constraints. The proline-based nitrogen and the Pra side-chain can be handled via protecting-group strategies to enable sequential transformations with controlled chemoselectivity and minimized side reactions. Synthesized intermediates derived from H-L-Pra-OH can feed into manufacturing sequences for peptide-like scaffolds, peptidomimetic candidates, and structure-defined research materials used in applied chemical development.
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