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    200616-39-3

    Catalog No. EBD46432

    CAS 200616-39-3

    Name Fmoc-L-Glu(2-phenylisopropyloxy)-OH

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    Basic Information

    Synonyms: Fmoc-Glu(O-2-Phipr)-Oh N-[(9H-Fluoren-9-ylmethoxy)carbonyl]-L-glutamicacid5-(1-methyl-1-phenylethyl)ester Fmoc-L-Glu(2-phenylisopropyloxy)-OH

    Molecular Formula: C29H29NO6

    Molecular Weight: 487.54

    Categories: Medicinal Chemistry > Biochemicals and Life Science Reagents > Peptides and Peptidomimetics Medicinal Chemistry > Pharmaceutical Intermediates > Drug Synthesis Building Blocks

    Product Description:
    Fmoc-L-Glu(2-phenylisopropyloxy)-OH is a protected derivative of L-glutamic acid. Its structure features an Fmoc (9-fluorenylmethoxycarbonyl) group protecting the alpha-amino group and a 2-phenylisopropyl (O-2-Ph-i-Pr) ester protecting the side-chain gamma-carboxylic acid. This specific protection strategy renders the side chain orthogonal to standard Fmoc deprotection conditions. This compound is a specialized, non-natural amino acid building block primarily used in solid-phase peptide synthesis (SPPS) via the Fmoc strategy. The O-2-Ph-i-Pr protecting group on the glutamic acid side chain is stable under the basic conditions (e.g., piperidine) used to remove the Fmoc group during chain elongation. It is selectively cleaved under strong acid conditions, such as with hydrogen fluoride (HF) or trifluoromethanesulfonic acid (TFMSA), during the final global deprotection and cleavage from the resin. This allows for the controlled introduction of a free carboxylic acid functionality at a specific position in the peptide sequence post-synthesis. Its main application is in the research and development of complex peptides and peptidomimetics, where precise side-chain functionality is critical. It is a key reagent for introducing glutamic acid residues that require selective deprotection or for constructing peptides with branched or cyclic structures via side-chain ligation.
    Physical Properties

    Density: 1.249

    mg g kg ml l t