title: Hydrogen bonding to carbonyl oxygen of nitrogen-pyramidalized amide - detection of pyramidalization direction preference by vibrational circular dichroism spectroscopy.
abstract: Nitrogen-pyramidalization of amide increases electron density on nitrogen and decreases that on carbonyl oxygen. We identified hydrogen-bonding to carbonyl of nitrogen-pyramidalized bicyclic β-proline derivatives by crystallography, and by NMR and vibrational circular dichroism (VCD) spectroscopy in solution. Such hydrogen-bonding can switch the preferred nitrogen-pyramidalization direction, as detected by VCD spectroscopy.
authors.affiliation: Graduate School of Pharmaceutical Sciences, University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033, Japan. otani@mol.f.u-tokyo.ac.jp ohwada@mol.f.u-tokyo.ac.jp and Research Foundation Itsuu Laboratory, C1232 Kanagawa Science Park R & D Building, 3-2-1 Sakado, Takatsu-ku, Kawasaki, Kanagawa 213-0012, Japan.
authors.forename: Siyuan
authors.initials: S
authors.lastname: Wang
authors.affiliation: Frontier Research Center for Post-Genome Science and Technology, Faculty of Advanced Life Science, Hokkaido University, Kita 21 Nishi 11, Sapporo 001-0021, Japan.
authors.forename: Tohru
authors.initials: T
authors.lastname: Taniguchi
authors.affiliation: Frontier Research Center for Post-Genome Science and Technology, Faculty of Advanced Life Science, Hokkaido University, Kita 21 Nishi 11, Sapporo 001-0021, Japan.
authors.forename: Kenji
authors.initials: K
authors.lastname: Monde
authors.affiliation: Faculty of Pharmaceutical Sciences at Kagawa Campus, Tokushima Bunri University, 1314-1 Shido, Sanuki, Kagawa 769-2193, Japan.
authors.forename: Masatoshi
authors.initials: M
authors.lastname: Kawahata
authors.affiliation: Faculty of Pharmaceutical Sciences at Kagawa Campus, Tokushima Bunri University, 1314-1 Shido, Sanuki, Kagawa 769-2193, Japan.
authors.forename: Kentaro
authors.initials: K
authors.lastname: Yamaguchi
authors.affiliation: Graduate School of Pharmaceutical Sciences, University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033, Japan. otani@mol.f.u-tokyo.ac.jp ohwada@mol.f.u-tokyo.ac.jp.
authors.forename: Yuko
authors.initials: Y
authors.lastname: Otani
authors.affiliation: Graduate School of Pharmaceutical Sciences, University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033, Japan. otani@mol.f.u-tokyo.ac.jp ohwada@mol.f.u-tokyo.ac.jp.
authors.forename: Tomohiko
authors.initials: T
authors.lastname: Ohwada
mesh_terms: D000577:Amides / Q000737:chemistry*; D002942:Circular Dichroism; D006860:Hydrogen Bonding; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D009584:Nitrogen / Q000737:chemistry*; D010100:Oxygen / Q000737:chemistry*; D011743:Pyrimidines / Q000737:chemistry*
chemical_list: D000577:Amides; D011743:Pyrimidines; C030986:pyrimidine; D009584:Nitrogen; D010100:Oxygen