Highly efficient synthesis of DNA-binding hairpin polyamides via the use of a new triphosgene coupling strategy

Wu Su; Stephen J Gray; Ruggero Dondi; Glenn Burley

doi:10.1021/ol9015139

Highly efficient synthesis of DNA-binding hairpin polyamides via the use of a new triphosgene coupling strategy

Wu Su, Stephen J Gray, Ruggero Dondi, Glenn Burley

Pure And Applied Chemistry

Research output: Contribution to journal › Article › peer-review

25 Citations (Scopus)

Abstract

A facile and highly efficient solid phase synthesis method is reported for the preparation of hairpin DNA-binding polyamides using the cost-effective
triphosgene (BTC) activating agent. Difficult polyamide sequences were prepared from N-methylimidazole (Im) and N-methylpyrrole (Py) building blocks with high stepwise yields (>98%) using Boc chemistry. The versatility of the triphosgene coupling approach was also demonstrated for the first time on aryl hydrazine resins to afford biomedically relevant tail-truncated polyamides in excellent isolated yields.

Original language	English
Pages (from-to)	3910-3913
Number of pages	4
Journal	Organic Letters
Volume	11
Issue number	17
Early online date	11 Aug 2009
DOIs	https://doi.org/10.1021/ol9015139
Publication status	Published - 3 Sept 2009

Keywords

solid phase synthesis
hairpin DNA-binding polyamides
polyamide sequences

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10.1021/ol9015139

New Molecular Tools For The 21st Century: Molecular Design Of New DNA-Based Devices
Burley, G. (Principal Investigator)
EPSRC (Engineering and Physical Sciences Research Council)
1/04/12 → 31/03/13
Project: Research Fellowship

Cite this

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title = "Highly efficient synthesis of DNA-binding hairpin polyamides via the use of a new triphosgene coupling strategy",

abstract = "A facile and highly efficient solid phase synthesis method is reported for the preparation of hairpin DNA-binding polyamides using the cost-effective triphosgene (BTC) activating agent. Difficult polyamide sequences were prepared from N-methylimidazole (Im) and N-methylpyrrole (Py) building blocks with high stepwise yields (>98%) using Boc chemistry. The versatility of the triphosgene coupling approach was also demonstrated for the first time on aryl hydrazine resins to afford biomedically relevant tail-truncated polyamides in excellent isolated yields.",

keywords = "solid phase synthesis , hairpin DNA-binding polyamides , polyamide sequences ",

author = "Wu Su and Gray, {Stephen J} and Ruggero Dondi and Glenn Burley",

year = "2009",

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doi = "10.1021/ol9015139",

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T1 - Highly efficient synthesis of DNA-binding hairpin polyamides via the use of a new triphosgene coupling strategy

AU - Su, Wu

AU - Gray, Stephen J

AU - Dondi, Ruggero

AU - Burley, Glenn

PY - 2009/9/3

Y1 - 2009/9/3

N2 - A facile and highly efficient solid phase synthesis method is reported for the preparation of hairpin DNA-binding polyamides using the cost-effective triphosgene (BTC) activating agent. Difficult polyamide sequences were prepared from N-methylimidazole (Im) and N-methylpyrrole (Py) building blocks with high stepwise yields (>98%) using Boc chemistry. The versatility of the triphosgene coupling approach was also demonstrated for the first time on aryl hydrazine resins to afford biomedically relevant tail-truncated polyamides in excellent isolated yields.

AB - A facile and highly efficient solid phase synthesis method is reported for the preparation of hairpin DNA-binding polyamides using the cost-effective triphosgene (BTC) activating agent. Difficult polyamide sequences were prepared from N-methylimidazole (Im) and N-methylpyrrole (Py) building blocks with high stepwise yields (>98%) using Boc chemistry. The versatility of the triphosgene coupling approach was also demonstrated for the first time on aryl hydrazine resins to afford biomedically relevant tail-truncated polyamides in excellent isolated yields.

KW - solid phase synthesis

KW - hairpin DNA-binding polyamides

KW - polyamide sequences

U2 - 10.1021/ol9015139

DO - 10.1021/ol9015139

M3 - Article

SN - 1523-7060

VL - 11

SP - 3910

EP - 3913

JO - Organic Letters

JF - Organic Letters

IS - 17

ER -

Highly efficient synthesis of DNA-binding hairpin polyamides via the use of a new triphosgene coupling strategy

Abstract

Keywords

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New Molecular Tools For The 21st Century: Molecular Design Of New DNA-Based Devices

Cite this