The 2-(4-trifluoromethylphenylsulfonyl)ethoxycarbonyl (Tsc) amino-protecting group: Use in the solid-phase synthesis of pyrrole-imidazole polyamides

Jin Seok Choi, Younjoo Lee, Eunmyoung Kim, Nakcheol Jeong, Hosung Yu, Hogyu Han

    Research output: Contribution to journalArticlepeer-review

    11 Citations (Scopus)

    Abstract

    The development of the 2-(4-trifluoromethylphenylsulfonyl)ethoxycarbonyl (Tsc) function, a novel base-sensitive amino-protecting group, and its application to the preparation of DNA-binding polyamides are described. Pyrrole-imidazole polyamides were synthesized by an efficient solid-phase method under conditions compatible with Fmoc chemistry using two Tsc-protected amino acids, Tsc-Py-OH 1a and Tsc-Im-OH 1b.

    Original languageEnglish
    Pages (from-to)1607-1610
    Number of pages4
    JournalTetrahedron Letters
    Volume44
    Issue number8
    DOIs
    Publication statusPublished - 2003 Feb 17

    Bibliographical note

    Funding Information:
    This work was financially supported by the Basic Research (Grant No. 981-0302-009-2) and CRM programs from KOSEF. Fellowship support from the BK21 program (J.S.C., Y.L., E.K.) is gratefully acknowledged.

    Copyright:
    Copyright 2008 Elsevier B.V., All rights reserved.

    Keywords

    • Amino acid
    • Amino protecting group
    • DNA
    • Distamycin
    • Tsc group

    ASJC Scopus subject areas

    • Biochemistry
    • Drug Discovery
    • Organic Chemistry

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