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    393568-74-6

    Catalog No. EBD3731025

    CAS 393568-74-6

    Name N-[(1,1-dimethylethoxy)carbonyl]-1-(triphenylmethyl)-D-Histidine

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    Basic Information

    Synonyms: N-[(1,1-dimethylethoxy)carbonyl]-1-(triphenylmethyl)-D-Histidine D-Histidine,N-[(1,1-dimethylethoxy)carbonyl]-1-(triphenylmethyl)- Boc-D-His(Trt)-OH

    Molecular Formula: C30H31N3O4

    Molecular Weight: 497.58

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

    Product Description:
    N-[tert-Butoxycarbonyl]-1-(triphenylmethyl)-D-histidine is a protected derivative of the amino acid D-histidine. It features two key protective groups: the tert-butoxycarbonyl (Boc) group on the amine and the triphenylmethyl (trityl, Trt) group on the imidazole ring of the histidine side chain. This specific protection scheme is crucial for the synthesis of peptides containing histidine residues, particularly in solid-phase peptide synthesis (SPPS). This compound serves as a specialized, high-purity building block for the controlled incorporation of D-histidine into peptide sequences. The Boc group is acid-labile, allowing for selective deprotection during chain elongation, while the Trt group protects the imidazole nitrogen from side reactions and is typically removed under mild acidic conditions. Its primary application is in the research and development of pharmaceutical peptides, where D-amino acids like D-histidine are used to enhance metabolic stability, alter receptor selectivity, or modulate the pharmacokinetic properties of therapeutic peptides. As a non-natural, enantiomerically pure amino acid derivative, it is a critical intermediate in producing peptides for drug discovery, especially in areas targeting GPCRs, enzymes, and as potential antimicrobial or diagnostic agents. Handling requires standard precautions for fine chemicals, including storage in a cool, dry place.
    Physical Properties
    mg g kg ml l t