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. Author manuscript; available in PMC: 2013 Jul 24.

Published in final edited form as: J Comb Chem. 2010 Jan-Feb;12(1):111–118. doi: 10.1021/cc9001586

Fig. 4 — Stereoview of an overlap of an amphiphatic α-helix with two valine in i and i+6 positions (orange sticks) with a Gewald thiophene-derived dipeptide mimetic (blue sticks). The small molecule derived from aldehyde A7, cyanoacetamide B23, sulfur was deprotected and N-acylated and then energy minimized using MOLOC software.²⁸ An important feature of the Gewald-thiophene derivatives of cyanoacetamides is the intramolecular hydrogen bonding of the 2-amino group with the 3-amide carbonyl, reducing the conformational freedom of the amide group considerably. In support of the above hypothetical structure, the intramolecular hydrogen bridge can be seen in most of the published x-ray structure analysis.⁴

Fig. 4 — Stereoview of an overlap of an amphiphatic α-helix with two valine in i and i+6 positions (orange sticks) with a Gewald thiophene-derived dipeptide mimetic (blue sticks). The small molecule derived from aldehyde A7, cyanoacetamide B23, sulfur was deprotected and N-acylated and then energy minimized using MOLOC software.²⁸ An important feature of the Gewald-thiophene derivatives of cyanoacetamides is the intramolecular hydrogen bonding of the 2-amino group with the 3-amide carbonyl, reducing the conformational freedom of the amide group considerably. In support of the above hypothetical structure, the intramolecular hydrogen bridge can be seen in most of the published x-ray structure analysis.⁴