Solid-Phase Synthesis of Water-Soluble Helically Folded Hybrid α‑Amino Acid/Quinoline Oligoamides

We report here a solid phase synthesis methodology that allows the incorporation of α-amino acids (X) into quinoline (Q) oligoamide foldamer sequences. Water-soluble hybrid oligoamides based on the XQ 2 trimer repeat motif were shown to adopt helical conformations presenting α-amino acid side chains...

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Veröffentlicht in:	Journal of organic chemistry 2016-02, Vol.81 (3), p.1137-1150
Hauptverfasser:	Hu, Xiaobo, Dawson, Simon J, Nagaoka, Yui, Tanatani, Aya, Huc, Ivan
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Sprache:	eng
Schlagworte:	Chemical Sciences Organic chemistry
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container_end_page	1150
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container_title	Journal of organic chemistry
container_volume	81
creator	Hu, Xiaobo Dawson, Simon J Nagaoka, Yui Tanatani, Aya Huc, Ivan
description	We report here a solid phase synthesis methodology that allows the incorporation of α-amino acids (X) into quinoline (Q) oligoamide foldamer sequences. Water-soluble hybrid oligoamides based on the XQ 2 trimer repeat motif were shown to adopt helical conformations presenting α-amino acid side chains in a predictable linear array on one face of the helix. In contrast, sequences based on the XQ dimer motif expressed less well-defined behavior, most likely due to local conformational variability precluding long-range order. Also presented is a full structural investigation by NMR of a dodecameric XQ 2 -type foldamer containing four different amino acid residues (Lys, Ala, Asp, and Ser).
doi_str_mv	10.1021/acs.joc.5b02671
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Org. Chem</addtitle><date>2016-02-05</date><risdate>2016</risdate><volume>81</volume><issue>3</issue><spage>1137</spage><epage>1150</epage><pages>1137-1150</pages><issn>0022-3263</issn><eissn>1520-6904</eissn><abstract>We report here a solid phase synthesis methodology that allows the incorporation of α-amino acids (X) into quinoline (Q) oligoamide foldamer sequences. Water-soluble hybrid oligoamides based on the XQ 2 trimer repeat motif were shown to adopt helical conformations presenting α-amino acid side chains in a predictable linear array on one face of the helix. In contrast, sequences based on the XQ dimer motif expressed less well-defined behavior, most likely due to local conformational variability precluding long-range order. 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title	Solid-Phase Synthesis of Water-Soluble Helically Folded Hybrid α‑Amino Acid/Quinoline Oligoamides
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