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Synlett 2010(10): 1544-1548  
DOI: 10.1055/s-0029-1219925
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

Solid-Phase Synthesis of (ω-Aminoalkyl)peptoids Using Azide Chemistry

Daniel Fritz, Stefan Bräse*
Karlsruhe Institute of Technology, Institute of Organic Chemistry, Fritz-Haber-Weg 6, 76131 Karlsruhe, Germany
Fax: +49(721)6088581; e-Mail: braese@kit.edu;
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Publication History

Received 7 March 2010
Publication Date:
10 May 2010 (online)

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Abstract

Functionalized (ω-aminoalkyl)peptoids - useful molecular transporters for drugs and probes into cells - have been synthesized by a combined microwave-assisted sub-monomer peptoid synthesis with 1-amino-ω-azidoalkanes and a subsequent reduction of the azide moiety on solid supports. This method enables the preparation of unprecedented chiral amino-functionalized and PEG-type peptoids. Both the scope and limitations of this process are presented herein.

Key words

peptoid - amines - azides - peptidomimetic transporters - solid-phase synthesis - microwave synthesis - protecting groups

    References and Notes

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8

CAUTION: Short chained 1-halo-ω-azidoalkanes might be explosive. We recommend the use of alkanes with at least six carbon atoms in case diazidoalkanes are formed. For a discussion, see ref. 9