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- W2893418429 abstract "Tigecycline is an antibacterial drug in the tetracycline class. In electrospray mass spectrometry both singly-protonated (MH+) and doubly-protonated molecules (MH22+) are formed in abundance. The major fragmentation reactions of the molecular ions in both charge states take place around the amido group at the C2-position on the A-ring and the t-butylamino group of the side chain at the C9-position on the D-ring. Deuterium labeling reveals that losses of ammonia from C2 and isobutene from C9 from both MH+ and MH22+ take place in a consecutive fashion, and elimination of the constitutive t-butylamine as a distinct neutral species does not occur as suggested intuitively. In addition, it is found that the elimination of isobutene from MH22+ is more than 10-fold as much as that from MH+ relative to the ammonia loss. This suggests that in the “double engine” molecular ion (MH22+), the first protonation occurs on the N,N-dimethylamino substituent on the A-ring, responsible for the loss of ammonia from the adjacent C2-amido group, and the second protonation occurs on the t-butylamino moiety on the D-ring to initiate the removal of isobutene. Since these two reactions are also observed with the “single engine” molecular ion (MH+), it is clear that upon the first neutral loss (either ammonia or isobutene), a proton is required to travel across the tetracycline core to trigger the second neutral loss. Multistage mass spectrometry confirms that the structure of the final product ion is the same regardless of the order in which the two neutral species are eliminated, supporting the requirement for a long-range proton migration." @default.
- W2893418429 created "2018-10-05" @default.
- W2893418429 creator A5091740382 @default.
- W2893418429 date "2018-11-01" @default.
- W2893418429 modified "2023-09-23" @default.
- W2893418429 title "Dissociative protonation and long-range proton migration: The chemistry of singly- and doubly-protonated tigecycline" @default.
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- W2893418429 doi "https://doi.org/10.1016/j.ijms.2018.09.025" @default.
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