L-Proline amide hydrochloride is a proline-derived amino acid derivative in which the carboxyl group is converted to an amide and the molecule is present as a hydrochloride salt. The structure retains the secondary cyclic pyrrolidine ring side chain of proline and bears an amino functionality as part of the proline amide framework, with hydrochloride providing counterion association to support handling and solubility. In peptide chemistry and related synthetic workflows, it is used as a building-block precursor to introduce the proline amide motif or to generate further protected or activated derivatives for incorporation into amide-linked structures and for analytical method development involving proline-containing standards.
CAT No: CP01717
CAS No:42429-27-6
Synonyms/Alias:L-Prolinamidehydrochloride;42429-27-6;(S)-Pyrrolidine-2-carboxamidehydrochloride;L-Prolineamidehydrochloride;(2S)-pyrrolidine-2-carboxamidehydrochloride;L-ProlinamideHCl;PubChem13020;prolinamidehydrochloride;prolineamidehydrochloride;P5010_SIGMA;SCHEMBL241227;81721_FLUKA;CTK7D2294;CSKSDAVTCKIENY-WCCKRBBISA-N;MolPort-003-939-163;(S)-Pyrrolidine-2-carboxamideHCl;EINECS255-818-2;AKOS016843692;AM82206;L-(-)-PROLINAMIDEHYDROCHLORIDE;AK113916;I500;KB-53369;(2S)-2-pyrrolidinecarboxamidehydrochloride;DB-050912
L-Proline amide hydrochloride is an L-configured proline-derived amide salt in which the cyclic secondary amine of proline is retained while the carboxyl functionality is converted to an amide, and the remaining basic nitrogen is present as a hydrochloride. The molecule therefore presents a chiral, conformationally constrained pyrrolidine ring alongside a neutral amide carbonyl that can participate in hydrogen-bonding and peptide-like recognition. Salt formation with hydrochloride modulates basicity and improves handling of the amino acid derivative in synthetic workflows, while the amide functionality provides a stable, non-zwitterionic handle for downstream coupling or functional group interconversion. The stereochemical integrity of the L-proline framework supports stereocontrolled synthesis of proline-containing motifs used in peptide chemistry and chiral intermediate preparation.
1. Peptide Coupling Chemistry
L-Proline amide hydrochloride is applied in peptide synthesis planning where proline-like conformational constraints are required without exposing a free carboxyl group. The retained L-stereocenter on the pyrrolidine ring and the amide carbonyl enable incorporation of proline-derived fragments into larger amide-rich scaffolds through sequential coupling strategies that rely on orthogonal activation of other partners. The hydrochloride form can be used to manage protonation state during protection/deprotection logic, supporting reproducible formation of new amide bonds in solution-phase synthesis. Proline amide building blocks generated from this material can serve as intermediates for constructing proline-containing peptides, peptidomimetics, and constrained backbone analogs that probe backbone-dependent recognition.
2. Chiral Amino Acid Intermediate
L-Proline amide hydrochloride functions as a chiral amino acid intermediate for stereoselective synthesis of proline-based derivatives used in fine chemical production and research-grade chiral library generation. The L-configuration on the pyrrolidine ring provides a defined stereochemical element that can be transferred into downstream products such as substituted proline amides, ring-functionalized analogs, and stereochemically defined constraints for SAR studies. The amide carbonyl and secondary amine geometry support selective derivatization routes, including N-functionalization and carbonyl-directed transformations that preserve stereochemical outcomes. Downstream conversion into protected or activated proline-related building blocks can support chiral synthesis workflows where consistent stereochemical identity is required for analytical comparability and structure-defined synthesis.
3. Chemical Biology Probes
L-Proline amide hydrochloride is suitable for chemical biology research where proline-containing, amide-bearing motifs are used to modulate binding interactions in peptide-like systems. The conformationally constrained pyrrolidine ring and the amide carbonyl can participate in hydrogen bonding and secondary-structure mimicry, enabling design of small-molecule probes and linker fragments that resemble proline-rich segments. Hydrochloride salt formation can aid solubility and reproducible handling when preparing conjugation-ready intermediates for labeling or affinity reagent construction. Generated derivatives can be used as scaffold components in biochemical assays, molecular recognition studies, and probe synthesis where stereodefined proline chemistry improves interpretability of structure-function relationships.
4. Pharmaceutical Intermediate Preparation
L-Proline amide hydrochloride is used in pharmaceutical intermediate preparation for constructing amide-rich intermediates and constrained nitrogen-containing fragments common to medicinal chemistry. The stable amide functionality and L-configured pyrrolidine framework support conversion into substituted proline amide analogs, N-derivatized intermediates, and C/N-functionalized derivatives that can feed into larger drug-like scaffolds. Hydrochloride salt behavior can be leveraged to control protonation during intermediate isolation and subsequent functional group transformations, aligning with process chemistry needs for reproducible handling. Downstream products derived from this material can serve as building blocks for synthesis of proline-containing peptidomimetics and heterocycle-adjacent structures used in industrial fine chemical manufacturing.
5. Analytical Reference Standards
L-Proline amide hydrochloride is applicable to analytical research as a stereochemically defined reference material for method development and impurity profiling of proline-derived amide intermediates. The combination of an L-configured pyrrolidine ring, an amide carbonyl, and hydrochloride salt form provides characteristic chromatographic and spectroscopic signatures that can be used to verify identity during protected amino acid synthesis and peptide coupling workflows. The non-zwitterionic, amide-bearing structure can help establish retention behavior and fragmentation patterns relevant to LC-MS, NMR, and IR characterization of related proline derivatives. Reference standards prepared from this compound can support quality-by-design approaches in chemical manufacturing, where consistent stereochemical and functional group identity is required for reliable analytical interpretation.
6. Side-Chain Functionalization Building Block
L-Proline amide hydrochloride supports side-chain functionalization strategies used to generate substituted proline amides and constrained linkers for peptide science and materials-oriented chemistry. The secondary amine within the pyrrolidine ring can undergo controlled N-derivatization, enabling formation of N-protected or N-activated intermediates that participate in subsequent coupling steps or conjugation chemistry. The amide carbonyl provides a persistent functional group for further transformation into urea-like motifs, acyl transfer intermediates, or hydrogen-bonding-directed scaffolds. Downstream functionalized derivatives can be employed to build proline-containing peptidomimetics, polymerizable amino acid analogs, and specialty chemical intermediates where stereodefined proline structure influences reactivity and molecular recognition.
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