Peptide mimics to control protein functions on the surface of proteins

2016 Fiscal Year Final Research Report

• Project/Area Number: 26293002
• Research Category: Grant-in-Aid for Scientific Research (B)
• Allocation Type: Partial Multi-year Fund
• Section: 一般
• Research Field: Chemical pharmacy
• Research Institution: The University of Tokyo
• Principal Investigator: OHWADA Tomohiko 東京大学, 薬学研究科(研究院), 教授 (20177025)
• Research Collaborator: FIRMAN ; INOMATA Satoru ; ZHAI Luhan ; OCAMPO Diego ; OTANI Yuko ; IKEDA Hirotaka ; KAWAHATA Masatoshi ; YAMAGUCHI Kentaro
• Project Period (FY): 2014-04-01 – 2017-03-31
• Keywords: ペプチド / 水素結合 / ヘリックス / S-NO化

Outline of Final Research Achievements

The amide bond is a key linkage in proteins, peptides and peptide mimics, serving to connect two neighbouring amino acids or analogues. Most amide bonds are planar, but nonplanar amide structures have been suggested to occur even in proteins and peptides. Although the magnitude of nonplanarity found in proteins and peptides is not large, some nonplanar amides with distinct ground states have been reported. In such non-planar amides, the nitrogen atom gains a partial sp3-character (i.e., nitrogen-pyramidalization), and at the same time bond-twisting occurs. While hydrogen-bonding to the pyramidalized electron-rich nitrogen atom has been experimentally and computationally investigated, there has been little study on the possibility of hydrogen bonding to the electron-deficient carbonyl oxygen atom of non-planar amides. We studied hydrogen bonding of 7-azabicyclo[2.2.1]heptane amides, which are chemically stable and intrinsically nonplanar.

Free Research Field

化学系薬学（有機化学）