Decomposition of protonated threonine, its stereoisomers, and its homologues in the gas phase: Evidence for internal backside displacement

Scott V. Serafin, Kangling Zhang, Luigi Aurelio, Andrew B. Hughes, Thomas Hellman Morton

Research output: Contribution to journalArticle

17 Scopus citations


Protonated threonine and its allo diastereomer exhibit different proportions of collisionally activated dissociation (CAD) product ions. N-Methylation attenuates these differences. Water loss from protonated allo-threonine gives protonated trans-3-methylaziridinecarboxylic acid via an internal SN2 pathway, rather than protonated vinylglycine.

Original languageEnglish (US)
Pages (from-to)1561-1564
Number of pages4
JournalOrganic Letters
Issue number10
StatePublished - May 13 2004
Externally publishedYes


ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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