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    273222-05-2

    Catalog No. EBD2321411

    CAS 273222-05-2

    Name (2R,4R)-4-Alloc-amino-1-Fmoc-Pyrrolidine-2-carboxylic acid

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    Basic Information

    Synonyms: 1,2-Pyrrolidinedicarboxylicacid,4-[[(2-propen-1-yloxy)carbonyl]amino]-,1-(9H-fluoren-9-ylmethyl)ester,(2S,4R)-

    Molecular Formula: C24H24N2O6

    Molecular Weight: 436.46

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

    Product Description:
    (4R)-1-Fmoc-4-(allyloxycarbonylamino)-L-proline is a protected L-proline derivative. Its structure features an L-proline core with two key protective groups: an Fmoc (9-fluorenylmethoxycarbonyl) group on the nitrogen of the pyrrolidine ring and an Alloc (allyloxycarbonyl) group on the side-chain amine at the 4-position. This specific combination of orthogonal protecting groups is crucial for its primary application. This compound is a specialized building block in solid-phase peptide synthesis (SPPS). The Fmoc group is acid-stable but base-labile, allowing for its selective removal during standard Fmoc-based SPPS cycles. Conversely, the Alloc group on the side chain is stable under basic conditions but can be selectively removed under mild, neutral conditions using palladium catalysis. This orthogonality enables the synthesis of complex peptides, particularly those containing cyclic structures or requiring selective side-chain modifications, such as stapled peptides or peptides with post-translational modifications at specific proline residues. Its use is predominantly in advanced peptide research and the development of peptide-based therapeutics. The compound is not a general-purpose reagent but a high-value, application-specific intermediate designed for constructing sophisticated peptide architectures in medicinal chemistry and chemical biology.
    Physical Properties
    mg g kg ml l t