DataVXThe Journal of Physical Chemistry LettersPaper
journal article·2024-07-11Open access

The Gas Phase Protonation Sites of Six Naturally Occurring Nicotinoids

Yuika Okura, Garrett D. Santis, Keisuke Hirata, Sotiris S. Xantheas, Masaaki Fujii, Shun-Ichi Ishiuchi

The Journal of Physical Chemistry Letters· Volume 15· Issue 27
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Source abstract

Abstract

The gas phase protonation sites of six naturally occurring nicotinoids, namely nicotine (NIC), nornicotine (NOR), anabasine (ANB), anatabine (ANT), cotinine (COT), and myosmine (MYO), consisting of a common Pyridine and differing non -Pyridine rings, have been determined for the first time at the physiological temperature from cryogenic ion trap infrared spectroscopy and electronic structure calculations. The protonation site on either of these two rings is related to the nicotinoid’s biological activity. At room temperature, NIC is a mixture of Pyridine and Pyrrolidine ( non -Pyridine) protomers, whereas NOR, ANB, ANT, and COT are pure Pyridine protomers and finally MYO is mostly a Pyroline ( non -Pyridine) protomer. The nearly planar structure of MYO-H +, induced by the presence of a conjugated π system and confirmed from calculations and the UV absorption spectra, breaks from the trends observed for NIC, NOR, and ANB, since its structure is drastically different from the structures of the other nicotinoids.
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Research context

OpenAlex topics: Nicotinic Acetylcholine Receptors Study · Mass Spectrometry Techniques and Applications · Synthesis and Biological Evaluation

SciVX discovery tags are terminology-based. OpenAlex topics are source-provided classifications.

Affiliations

Department of Chemistry, School of Science, Tokyo Institute of Technology, 2-12-1 4259 Ookayama, Meguro-ku, Tokyo 152855, Japan

Department of Chemistry, University of Washington, Seattle, Washington 98195, United States

World Research Hub Initiative (WRHI), Institute of Innovation Research, Tokyo Institute of Technology, 4259 Nagatsuta-cho, Midori-ku, Yokohama 226-8503, Japan

Advanced Computing, Mathematics and Data Division, Pacific Northwest National Laboratory, 902 Battelle Boulevard, P.O. Box 999, MS J7-10 Richland, Washington 99352, United States

Computational and Theoretical Chemistry Institute (CTCI), Pacific Northwest National Laboratory, Richland, Washington 99352, United States

Laboratory for Chemistry and Life Science, Institute of Innovative Research, Tokyo Institute of Technology, 4259 Nagatsuta-cho, Midori-ku, Yokohama 226-8503, Japan

Research and Development Initiative, Chuo University, 1-13-27 Kasuga, Bunkyo-ku, Tokyo 112-8551, Japan

Funding

Japan Society for the Promotion of Science · Office of Science

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