Multimatrix Variation Matrix-Assisted Laser Desorption/Ionization Mass Spectrometry as a Tool for Determining the Bonding of Nitrogen Atoms in Alkaloids.

Autor: Yamagaki T; Bioorganic Research Institute, Suntory Foundation for Life Sciences, 8-1-1 Seikadai, Seika-cho, Soraku-gun, Kyoto 619-0284, Japan., Osawa T; Bioorganic Research Institute, Suntory Foundation for Life Sciences, 8-1-1 Seikadai, Seika-cho, Soraku-gun, Kyoto 619-0284, Japan., Fujikawa K; Bioorganic Research Institute, Suntory Foundation for Life Sciences, 8-1-1 Seikadai, Seika-cho, Soraku-gun, Kyoto 619-0284, Japan., Watanabe T; Bioorganic Research Institute, Suntory Foundation for Life Sciences, 8-1-1 Seikadai, Seika-cho, Soraku-gun, Kyoto 619-0284, Japan., Sugahara K; Bioorganic Research Institute, Suntory Foundation for Life Sciences, 8-1-1 Seikadai, Seika-cho, Soraku-gun, Kyoto 619-0284, Japan.
Jazyk: angličtina
Zdroj: Journal of the American Society for Mass Spectrometry [J Am Soc Mass Spectrom] 2022 Dec 07; Vol. 33 (12), pp. 2243-2249. Date of Electronic Publication: 2022 Nov 15.
DOI: 10.1021/jasms.2c00221
Abstrakt: The reactivity of alkaloids in dehydrogenation was investigated using multimatrix variation matrix-assisted laser desorption/ionization mass spectrometry (MALDI-MS) of over 20 different alkaloids with six matrices. The dehydrogenated molecular ions [M - H] + generated by in-source decay were detected in the MALDI mass spectra of some types of alkaloids such as reserpine. The dehydrogenation proceeded at the cyclic tertiary amine rather than double-bonded nitrogen atoms and indole rings involved in the electron-delocalized systems. The stable protonated primary amines hindered dehydrogenation. The laser-induced dehydrogenation correlated with the chemical properties and structures of alkaloids. Alkaloids were classified into three types by the ratio of dehydrogenation by comparing the relative abundances of [M - H] + , [M] •+ , and [M + H] + ions in α-cyano-4-hydroxycinnamic acid and 5-formylsalicylic acid matrices. Structural isomers were also discriminated by this method of analyzing the three molecular ions' ratio using multimatrix variation MALDI-MS.
Databáze: MEDLINE
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