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11. Role of the solvent on the stability of cycloserine under ESI-MS conditions.

Author

Fraschetti C, Filippi A, Mannina L, Sobolev AP, and Speranza M

Subjects
Acetonitriles chemistry, Cycloserine analysis, Dimerization, Drug Stability, Magnetic Resonance Spectroscopy, Methanol chemistry, Cycloserine chemistry, Solvents chemistry, Spectrometry, Mass, Electrospray Ionization methods
Abstract

The effects of methanol (M) and acetonitrile (A) on the stability of cycloserine (1) have been studied. InfraRed Multiphoton PhotoDissociation (IRMPD) spectroscopy of the ionic species from electrospray ionization tandem mass spectrometry (ESI-MS) of 1/M and 1/A solutions points to extensive dimerization of 1 to cis-3,6-bis(aminooxymethyl)-2,5-piperidinedione (2), while the same process is not observed in the ESI-MS of 1/M solutions. 1D and 2D nuclear magnetic resonance experiments confirmed these findings by showing that partial dimerization of 1 actually takes place at room temperature in acetonitrile even before ESI-MS analysis. Comparison of nuclear magnetic resonance and IRMPD spectroscopic data from the same 1/A solution suggests that dimerization of cycloserine is enhanced in the ESI source., (Copyright © 2014 John Wiley & Sons, Ltd.)

Published
2014
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