Issue 21, 2016
From the journal:

Chemical Communications

Hydrogen bonding to carbonyl oxygen of nitrogen-pyramidalized amide – detection of pyramidalization direction preference by vibrational circular dichroism spectroscopy†

Siyuan Wang,‡ab   Tohru Taniguchi,‡c   Kenji Monde,c   Masatoshi Kawahata,d   Kentaro Yamaguchi,d   Yuko Otani*a  and  Tomohiko Ohwada*a  

* Corresponding authors

a Graduate School of Pharmaceutical Sciences, University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033, Japan
E-mail: otani@mol.f.u-tokyo.ac.jp, ohwada@mol.f.u-tokyo.ac.jp

b Research Foundation Itsuu Laboratory, C1232 Kanagawa Science Park R & D Building, 3-2-1 Sakado, Takatsu-ku, Kawasaki, Kanagawa 213-0012, Japan

c Frontier Research Center for Post-Genome Science and Technology, Faculty of Advanced Life Science, Hokkaido University, Kita 21 Nishi 11, Sapporo 001-0021, Japan

d Faculty of Pharmaceutical Sciences at Kagawa Campus, Tokushima Bunri University, 1314-1 Shido, Sanuki, Kagawa 769-2193, Japan

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.

Graphical abstract: Hydrogen bonding to carbonyl oxygen of nitrogen-pyramidalized amide – detection of pyramidalization direction preference by vibrational circular dichroism spectroscopy

  • This article is part of the themed collection: Foldamers
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Article information

DOI
https://doi.org/10.1039/C6CC00284F
Article type
Communication
Submitted
12 Phe 2016
Accepted
12 Kol 2016
First published
18 Kol 2016
This article is Open Access
Creative Commons BY license

Chem. Commun., 2016,52, 4018-4021

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Hydrogen bonding to carbonyl oxygen of nitrogen-pyramidalized amide – detection of pyramidalization direction preference by vibrational circular dichroism spectroscopy

S. Wang, T. Taniguchi, K. Monde, M. Kawahata, K. Yamaguchi, Y. Otani and T. Ohwada, Chem. Commun., 2016, 52, 4018 DOI: 10.1039/C6CC00284F

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