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Issue 19, 2011
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Efficient and versatile COMU-mediated solid-phase submonomer synthesis of arylopeptoids (oligomeric N-substituted aminomethyl benzamides)

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Abstract

The development of a highly efficient methodology for solid-phase synthesis of para- and meta-arylopeptoids (oligomeric N-substituted aminomethyl benzamides) with free acids or free amides at the C-terminus is described. The arylopeptoids were synthesised by means of a convenient submonomer protocol in which the arylopeptoid residues were created in an iterative manner on the growing chain using an acylation–substitution cycle. The uronium salt COMU was found to be the most efficient reagent for ensuring fast and clean couplings of the benzoic acid building blocks.

Graphical abstract: Efficient and versatile COMU-mediated solid-phase submonomer synthesis of arylopeptoids (oligomeric N-substituted aminomethyl benzamides)

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Publication details

The article was received on 09 May 2011, accepted on 06 Jul 2011 and first published on 12 Aug 2011


Article type: Paper
DOI: 10.1039/C1OB05729D
Org. Biomol. Chem., 2011,9, 6832-6843

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    Efficient and versatile COMU-mediated solid-phase submonomer synthesis of arylopeptoids (oligomeric N-substituted aminomethyl benzamides)

    T. Hjelmgaard, S. Faure, D. Staerk, C. Taillefumier and J. Nielsen, Org. Biomol. Chem., 2011, 9, 6832
    DOI: 10.1039/C1OB05729D

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