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    269078-69-5

    Catalog No. EBD2328307

    CAS 269078-69-5

    Name Fmoc-(2R,5S)-5-phenyl-pyrrolidine-2-carboxylic acid

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    Basic Information

    Synonyms: Fmoc-(2R,5S)-5-phenyl-pyrrolidine-2-carboxylicacid (2R,5S)-Fmoc-5-Phenyl-Pyrrolidine-2-CarboxylicAcid

    Molecular Formula: C26H23NO4

    Molecular Weight: 413.47

    MDL Number: MFCD01074695

    Categories: Medicinal Chemistry > Pharmaceutical Intermediates > Heterocyclic Intermediates Medicinal Chemistry > Biochemicals and Life Science Reagents > Peptides and Peptidomimetics

    Product Description:
    Fmoc-(2R,5S)-5-phenylpyrrolidine-2-carboxylic acid is a chiral, non-proteinogenic amino acid derivative. Its structure features a pyrrolidine ring substituted with a phenyl group at the 5-position and a carboxylic acid group at the 2-position, which is protected by a fluorenylmethyloxycarbonyl (Fmoc) group on the nitrogen. This specific stereochemistry (2R,5S) is crucial for its intended applications. This compound is primarily employed as a specialized building block in solid-phase peptide synthesis (SPPS). The Fmoc protecting group is standard for temporary N-terminal protection, allowing for iterative coupling cycles under mild basic conditions. The constrained, rigid structure of the phenyl-substituted pyrrolidine ring is designed to introduce conformational restrictions into synthetic peptides, which is a key strategy in medicinal chemistry for developing peptide-based therapeutics, enzyme inhibitors, or probes with enhanced metabolic stability, potency, and selectivity. Its use is almost exclusively within pharmaceutical research and development for constructing peptidomimetics and investigating structure-activity relationships (SAR). It is not a commodity chemical or a general-purpose synthetic reagent, but a high-value, application-specific intermediate for advanced peptide chemistry.
    Physical Properties
    mg g kg ml l t