Abstract
Gas-phase deprotonation reactions of cytochrome c ions by chiral amines (2-butylamine and 1-amino-2-propanol) exhibit strong chiral specificity. The R-isomer of 2-butylamine is at most 10 times more reactive than the S-isomer. With 1-amino-2-propanol, the R-isomer is as much as two times more reactive than the S isomer. The specificity decreases with increasing charge states. For the 12+ state, the (2R)-2-butylamine is only 50% more reactive than the S isomer, compared to 10 times for the 9+ state. Reactions of the racemic mixture of 1-amino-2-propanol and double resonance experiments suggest a complicated proton transfer mechanism possibly involving a diadducted intermediate - the protein with two alkyl amine adducts. Variable temperature experiments are also performed to illustrate the presence of a barrier in the proton transfer reaction.
Original language | English (US) |
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Pages (from-to) | 401-412 |
Number of pages | 12 |
Journal | International Journal of Mass Spectrometry |
Volume | 185 |
DOIs | |
State | Published - 1999 |
Keywords
- Chiral recognition
- Deprotonation reaction
- Gas phase
ASJC Scopus subject areas
- Physical and Theoretical Chemistry
- Spectroscopy
- Condensed Matter Physics
- Instrumentation