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

doi:10.1016/S0040-4039(03)00010-8

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 journal › Article › peer-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 language	English
Pages (from-to)	1607-1610
Number of pages	4
Journal	Tetrahedron Letters
Volume	44
Issue number	8
DOIs	https://doi.org/10.1016/S0040-4039(03)00010-8
Publication status	Published - 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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10.1016/S0040-4039(03)00010-8

Cite this

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

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.",

keywords = "Amino acid, Amino protecting group, DNA, Distamycin, Tsc group",

author = "Choi, {Jin Seok} and Younjoo Lee and Eunmyoung Kim and Nakcheol Jeong and Hosung Yu and Hogyu Han",

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.",

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doi = "10.1016/S0040-4039(03)00010-8",

language = "English",

volume = "44",

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T1 - The 2-(4-trifluoromethylphenylsulfonyl)ethoxycarbonyl (Tsc) amino-protecting group

T2 - Use in the solid-phase synthesis of pyrrole-imidazole polyamides

AU - Choi, Jin Seok

AU - Lee, Younjoo

AU - Kim, Eunmyoung

AU - Jeong, Nakcheol

AU - Yu, Hosung

AU - Han, Hogyu

N1 - 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.

PY - 2003/2/17

Y1 - 2003/2/17

N2 - 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.

AB - 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.

KW - Amino acid

KW - Amino protecting group

KW - DNA

KW - Distamycin

KW - Tsc group

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U2 - 10.1016/S0040-4039(03)00010-8

DO - 10.1016/S0040-4039(03)00010-8

M3 - Article

AN - SCOPUS:0037450391

SN - 0040-4039

VL - 44

SP - 1607

EP - 1610

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 8

ER -

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

Abstract

Bibliographical note

Keywords

ASJC Scopus subject areas

Access to Document

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