02 July 2015
Postdoc Jens Engel-Andreasen’s latest publication made the cover of The Journal of Organic Chemistry
A recent Full Article in The Journal of Organic Chemistry by lead author Jens Engel-Andreasen was selected for the cover illustration of the journal’s June 5th issue. The study was performed together with co-authors Kathrine Wich, Jonas S. Laursen, and Pernille Harris (from DTU) in the laboratory of Professor Christian A. Olsen at the Center for Biopharmaceuticals.
Peptoids constitute a class of peptidomimetics with potential as protease resistant, biologically active ligands. To harness the full potential of such compounds, however, detailed predictive insight into their propensity to adopt well-defined secondary structures is highly desirable. In this work, the authors presented an investigation of the effects of thioamides and/or fluorides in peptoid monomer model systems using chemical synthesis, NMR spectroscopy, and X-ray crystallography. They found that the steric environment surrounding the tertiary amide bonds is the key promoter of conformational preference.
The X-ray crystallographic interrogation of the model systems did not suggest the presence of stabilizing n → π* interactions unless the carbonyls were altered electronically by α-halogenation or thioamide formation. In addition to the role as investigative tools, these two types of modification may thus be utilized as stabilizers of secondary structure in future oligomer designs, such as cis-amide-based polypeptoid helices with biomedical potential.