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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