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Synfacts 2007(4): 0437-0437  
DOI: 10.1055/s-2007-968299
Polymer-Supported Synthesis
© Georg Thieme Verlag Stuttgart · New York

PEG-co-Oligo(p-benzamide)s Prepared on a Peptide Synthesizer

Contributor(s):Yasuhiro Uozumi, Yoichi M. A. Yamada
H. M. König, T. Gorelik, U. Kolb, A. F. M. Kilbinger*
Johannes Gutenberg-Universität Mainz, Germany
Supramolecular PEG-co-Oligo(p-benzamide)s Prepared on a Peptide Synthesizer
J. Am. Chem. Soc.  2007,  129:  704-708  
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Publication History

Publication Date:
23 March 2007 (online)

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Key words

automated synthesis - peptide synthesizer - oligo(p-benzamide)s - rod-coil conformation - aggregation

Significance

The first example of an automated oligo(p-benzamide) (OPBA) synthesis was demonstrated by use of a conventional peptide synthesizer employing a standard Fmoc-peptide synthesis protocol. Thus, an amino acid derivative 1 and Wang resin were subjected to the automatic peptide synthesizer to give a Wang resin supported OPBA heptamer 3g. Esterifcation of 3g with 4-pentynoyl chloride followed by cyclization with PEG-supported azide gave a Wang resin-PEG-supported OPBA heptamer 4. Acidic treatment of 4 afforded a PEG-supported OPBA heptamer 5.

Comment

The N-deprotected block co-oligomer 5 adopted a thermodynamically preferred rod-coil conformation and showed strong aggregation which was observed in chloroform, toluene and water.

TEM observation of 5 revealed rigid rod-like micelles stretching over several hundred nanometers.

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