L-Phenylalanine hydrazide contains the L-phenylalanine amino acid backbone with a phenyl side chain and an amide-linked hydrazide functionality at the carboxyl position, converting the free carboxyl group into a carboxylic acid hydrazide (-C(=O)NHNH2). The molecule retains the amino group on the alpha carbon and the hydrazide bears two nitrogen atoms capable of hydrogen bonding and acting as a nucleophilic/chelating handle under appropriate conditions, while the phenyl ring provides a hydrophobic aromatic side-chain. L-Phenylalanine hydrazide is employed as an amino acid derivative for preparing peptide-related intermediates, for hydrazide-based conjugation or labeling strategies, and for analytical or synthetic workflows that require a phenylalanine-derived building block with a reactive hydrazide moiety.
CAT No: CP01639
CAS No:52386-52-4
Synonyms/Alias:L-Phenylalaninehydrazide;52386-52-4;H-Phe-NHNH2;(S)-2-Amino-3-phenylpropanehydrazide;AC1LIIM3;SCHEMBL6423222;CTK8G0650;MolPort-016-581-051;ZINC5279132;7387AB;AKOS016368422;(2S)-2-amino-3-phenylpropanehydrazide;AM82186;MCULE-1732509159;AJ-53731;AK117103;KB-53355;K-9560
L-Phenylalanine hydrazide is an L-configured amino acid hydrazide derived from phenylalanine, retaining the stereogenic α-carbon of the natural amino acid while converting the carboxyl group into a hydrazide functionality. The molecule contains a primary hydrazide N-NH2 motif conjugated to the carbonyl, a benzyl side chain with a pendant phenyl ring, and a free amino acid backbone nitrogen that can participate in hydrogen bonding and acid-base equilibria. The hydrazide carbonyl and adjacent nucleophilic nitrogens enable chemoselective derivatization through acylation, condensation, and metal-chelation behavior typical of amino acid hydrazides. As a chiral amino acid derivative, it functions as a stereodefined intermediate for peptide-adjacent synthesis, heterocycle formation, and downstream functional group interconversion relevant to peptide chemistry and synthetic organic chemistry workflows.
1. Peptide Coupling Chemistry
L-Phenylalanine hydrazide is applied in peptide-adjacent synthesis where hydrazide-derived intermediates are used to access amide-forming or acyl-transfer pathways under peptide-compatible conditions. The L-phenylalanine scaffold provides a stereodefined α-amino center and a phenyl side chain that can be carried through coupling sequences, while the hydrazide carbonyl and terminal hydrazine can be transformed into activated acyl equivalents or converted into alternative nitrogen-containing linkers. Hydrazide chemistry supports formation of hydrazone intermediates and subsequent rearrangements that can generate peptide-like amide connectivity while maintaining the original chiral information. Downstream use includes preparation of chiral acylating agents and nitrogen-rich fragments for assembling peptide analogs and constrained peptidomimetic motifs.
2. Hydrazone And Condensation Chemistry
L-Phenylalanine hydrazide supports carbonyl derivatization in chemical biology and synthetic organic chemistry through condensation to form hydrazones with aldehydes and ketones. The hydrazide N-NH2 functionality reacts to generate C=N containing products that can be further functionalized via reduction, oxidation, or cyclization, enabling rapid construction of stereochemically informed scaffolds. The phenylalanine benzyl side chain offers hydrophobic and aromatic interaction features that can be leveraged in molecular recognition studies and in designing linkers for probe development. Resulting derivatives can serve as reaction handles for subsequent heterocycle synthesis or as analytical and structural probes that originate from a chiral amino acid precursor.
3. Heterocycle Synthesis
L-Phenylalanine hydrazide is suitable for heterocycle construction where amino acid hydrazides act as nucleophilic precursors to nitrogen-containing ring systems. The combination of a carbonyl-activated hydrazide and a terminal nucleophilic nitrogen can participate in cyclocondensation sequences to yield fused or pendant heterocycles while preserving the L-configuration at the α-carbon. The phenyl side chain contributes to regioselectivity and electronic tuning during ring formation, supporting access to chiral heterocyclic building blocks relevant to medicinal chemistry and peptidomimetic design. Downstream products include chiral heterocycle-containing intermediates that can be used for structure-activity relationship studies and for generating libraries of amino acid-derived scaffolds.
4. Bioconjugation Linker Development
L-Phenylalanine hydrazide is used in bioconjugation chemistry as a chiral hydrazide motif for constructing conjugates through hydrazone-based coupling strategies. The hydrazide group provides a reactive handle that can reversibly form hydrazone linkages with carbonyl-bearing biomolecules or tags, enabling controlled attachment and subsequent conversion to more stable linkages depending on the chosen chemistry. The amino acid-derived stereocenter and phenyl side chain can influence local conformation and hydrophobicity of the resulting conjugate, supporting design of linkers for affinity reagents and labeled biomolecule fragments. Resulting conjugation products can function as intermediates for chemical biology experiments, including probe generation and scaffold attachment to proteins or polymeric carriers.
5. Analytical Standards And Chiral Method Development
L-Phenylalanine hydrazide can be applied as a chiral reference material and derivatization reagent in analytical research targeting amino acid derivative profiling. The distinct hydrazide functional group provides strong spectroscopic signatures and can participate in derivatization reactions that improve detectability for LC-MS or chromatographic workflows. The L-phenylalanine backbone ensures stereospecific behavior associated with the α-chiral center, supporting method development for distinguishing hydrazide-containing amino acid species and related condensation products. Downstream utility includes preparation of calibration or qualification materials for monitoring amino acid hydrazide intermediates during chemical manufacturing and for verifying stereochemical integrity in peptide-adjacent synthesis routes.
6. Pharmaceutical Intermediate Preparation
L-Phenylalanine hydrazide is relevant to pharmaceutical intermediate preparation and process chemistry where hydrazides serve as nitrogen-rich intermediates for constructing amide and heterocycle-containing fragments. The protected amino acid derivative format, featuring a hydrazide carbonyl and terminal hydrazine, can be converted into activated acyl equivalents, cyclization precursors, or condensation-derived intermediates that integrate into larger synthetic sequences. The phenylalanine-derived side chain provides a stable aromatic handle that can be carried into downstream medicinal chemistry scaffolds without losing the stereodefined α-carbon. Broader manufacturing use includes fine chemical synthesis of chiral building blocks for peptide mimetics, heterocyclic drug-like structures, and other amino acid-derived intermediates where hydrazide reactivity is leveraged for controlled functional group transformation.
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