Chiral recognition and the deprotonation reaction of gas-phase cytochrome c ions

Shuinu Gong, Elvira Camara, Fei He, M. Kirk Green, Carlito B Lebrilla

Research output: Contribution to journalArticle

26 Scopus citations

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 languageEnglish (US)
Pages (from-to)401-412
Number of pages12
JournalInternational Journal of Mass Spectrometry
Volume185
DOIs
StatePublished - 1999

Keywords

  • Chiral recognition
  • Deprotonation reaction
  • Gas phase

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Spectroscopy
  • Condensed Matter Physics
  • Instrumentation

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