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 Citations (Scopus)

Abstract

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
Volume6
Issue number10
DOIs
StatePublished - May 13 2004
Externally publishedYes

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water loss
Stereoisomerism
methylation
Threonine
proportion
Gases
dissociation
vapor phases
Decomposition
decomposition
acids
Methylation
products
ions
Ions
Acids
Water
vinylglycine

ASJC Scopus subject areas

  • Molecular Medicine

Cite this

Decomposition of protonated threonine, its stereoisomers, and its homologues in the gas phase : Evidence for internal backside displacement. / Serafin, Scott V.; Zhang, Kangling; Aurelio, Luigi; Hughes, Andrew B.; Morton, Thomas Hellman.

In: Organic Letters, Vol. 6, No. 10, 13.05.2004, p. 1561-1564.

Research output: Contribution to journalArticle

Serafin, Scott V. ; Zhang, Kangling ; Aurelio, Luigi ; Hughes, Andrew B. ; Morton, Thomas Hellman. / Decomposition of protonated threonine, its stereoisomers, and its homologues in the gas phase : Evidence for internal backside displacement. In: Organic Letters. 2004 ; Vol. 6, No. 10. pp. 1561-1564.
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