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  • Title: [p-Sulfotetrafluorophenyl hydrophilic activated esters of amino acids in peptide synthesis].
    Author: Medvedkin VN, Zabolotskikh VF, Permiakov EA, Mitin IuV, Sorokina MN, Klimenko LV.
    Journal: Bioorg Khim; 1995 Sep; 21(9):684-90. PubMed ID: 8588813.
    Abstract:
    Highly reactive hydrophilic (i.e., water-soluble) p-sulfotetrafluorophenyl esters (Tfs esters) are proposed for peptide synthesis in aqueous and aqueous-organic media, as well as for protein and peptide partial synthesis in an aqueous medium. These esters can serve as a basis for creating a series of protein modifying reagents. As they are analogs of the widely used pentafluorophenyl esters, the Tfs esters possess a high reactivity coupled with good stability during storage. The expression for the reaction rate (for substrates AA1 and AA2) is shown to be v = k[Boc-AA1-OTfs][H-AA2-NH2]0.5 for both water and DMF, i.e., the reaction is not a simple second-order reaction. The reaction rate in water is only slightly lower than that in DMF.
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