Fmoc-alpha-Prg-L-Ala-OH is an Fmoc-protected amino acid derivative bearing an L-alanine core and an α-amino acid side chain that includes a propargyl (Prg) substituent, classifying it as a protected, structurally modified alanine suitable for peptide-related synthesis. The molecule contains an Fmoc carbamate on the α-amino group and a free carboxylic acid (-COOH), while the propargyl functionality provides a terminal alkyne handle for subsequent chemical modification, with stereochemistry indicated as L at the alanine center. In synthetic workflows such as solid-phase peptide synthesis or solution-phase assembly, the Fmoc protecting group supports stepwise coupling by controlling chemoselectivity, and the alkyne functionality enables downstream conjugation, labeling, or other alkyne-reactive transformations in chemical biology and biomaterials research.
CAT No: CP25207
CAS No:1198791-65-9
Synonyms/Alias:1198791-65-9;(R)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-2-methylpent-4-ynoicacid;SCHEMBL3434059;(2R)-2-[[(9H-Fluoren-9-ylmethoxy)carbonyl]amino]-2-methyl-4-pentynoicacid;MolPort-021-802-691;ZINC36914699;AKOS015950187;(R)-N-Fmoc-2-(2'-propynyl)alanine;AK162460
Chemical Name:N-alpha-(9-Fluorenylmethyloxycarbonyl)-alpha-propargyl-L-alanine, solvate with 20 to 50% MTBE (98%, 98%ee)
Fmoc-alpha-Prg-L-Ala-OH is an Fmoc-protected, L-alanine-based amino acid derivative in which the alpha-amino group is masked by the fluorenylmethoxycarbonyl (Fmoc) protecting group and the side chain is defined by a Prg (propargylglycine-like) functionality that introduces a chemically addressable handle for subsequent transformations. The molecule contains the canonical amino acid stereocenter at the alpha carbon, preserving L-configuration for stereochemically controlled peptide bond formation. The carboxylic acid remains available for coupling chemistry, while the side-chain propargyl-type motif can participate in orthogonal reactions such as click-type conjugations or selective derivatization after deprotection or under mild conditions. This protected amino acid scaffold is therefore positioned as a chiral peptide building block and synthetic intermediate for constructing functionalized peptide analogs and downstream chemical libraries.
1. Peptide Synthesis
Fmoc-alpha-Prg-L-Ala-OH supports automated and manual solid-phase peptide synthesis workflows by combining an Fmoc-protected alpha-amine with a free carboxylic acid for amide bond formation at the alanine position. The L-stereochemistry at the alpha carbon aligns with standard peptide coupling stereochemical outcomes, while the Prg side-chain functionality can be retained through coupling steps and later converted into orthogonal functionalities. Fmoc deprotection strategies enable sequential chain elongation, and the side-chain handle can be exploited for late-stage functionalization of the assembled peptide. Downstream peptide construction can thus generate Prg-bearing alanine segments for structure-activity relationship studies and functional peptide library generation.
2. Side-Chain Functionalization
Fmoc-alpha-Prg-L-Ala-OH is suited to side-chain functionalization programs because the Prg-derived propargyl-type motif provides a reactive chemical handle orthogonal to the protected amino acid backbone. The presence of an Fmoc group allows controlled timing of deprotection, enabling side-chain derivatization either after peptide assembly or on the free amino acid derivative depending on the chosen synthetic sequence. The carboxylic acid enables conversion into activated intermediates for further transformations, while the stereodefined alanine core helps maintain consistent spatial presentation in resulting conjugates. Functionalized products can be used to access labeled peptides, clickable linkers, or chemically modified amino acid analogs for biochemical research and applied materials chemistry.
3. Chemical Biology Conjugation
Fmoc-alpha-Prg-L-Ala-OH can be applied in chemical biology and biomolecule modification workflows where orthogonal conjugation chemistry is required after peptide incorporation. The Prg side-chain functionality can serve as a site for subsequent conjugation steps, enabling attachment of probes, affinity tags, or imaging handles to peptide-based scaffolds while keeping the peptide backbone compatible with standard coupling chemistry. The Fmoc-protected alpha-amine provides a protected, synthesis-ready format that supports controlled incorporation into peptide constructs before conjugation. Resulting Prg-functionalized peptide conjugates can be used for mechanistic studies, binding assays, and reagent preparation in biochemical research settings that rely on defined attachment points.
4. Peptidomimetics And SAR
Fmoc-alpha-Prg-L-Ala-OH is relevant to peptidomimetic and structure-activity relationship (SAR) programs because it introduces a stereodefined alanine residue bearing a chemically addressable side chain that can be transformed into diverse functional groups. The protected amino acid format supports incorporation into peptide analogs where the Fmoc strategy enables iterative assembly of analog series with consistent stereochemical control. The Prg handle can be used to generate a range of substituents that modulate polarity, steric profile, or conjugation capacity, supporting systematic SAR investigations through parallel synthesis. Downstream derivatives can serve as chemically defined intermediates for evaluating structure-function relationships in peptide-like scaffolds and biomolecular recognition studies.
5. Process Chemistry Intermediate
Fmoc-alpha-Prg-L-Ala-OH functions as a chiral, protected amino acid intermediate for fine chemical synthesis and process chemistry routes that require stable handling of an L-amino acid building block. The Fmoc protecting group provides a robust protection strategy for the alpha-amino functionality during coupling and intermediate formation, while the free carboxylic acid supports conversion to activated species for downstream manufacturing steps. The side-chain Prg functionality can be carried through controlled synthetic stages and then converted into targeted derivatives using orthogonal transformation logic aligned with protecting-group compatibility. Industrially, the compound can be utilized as a reproducible input for producing functionalized peptide building blocks, specialty chemical intermediates, and chemically addressable amino acid derivatives used in larger-scale synthesis programs.
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