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

doi:10.1021/ol049700p

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 journal › Article › peer-review

18 Scopus citations

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 S_N2 pathway, rather than protonated vinylglycine.

Original language	English (US)
Pages (from-to)	1561-1564
Number of pages	4
Journal	Organic Letters
Volume	6
Issue number	10
DOIs	https://doi.org/10.1021/ol049700p
State	Published - May 13 2004
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol049700p

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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.",

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T2 - Evidence for internal backside displacement

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AU - Zhang, Kangling

AU - Aurelio, Luigi

AU - Hughes, Andrew B.

AU - Morton, Thomas Hellman

PY - 2004/5/13

Y1 - 2004/5/13

N2 - 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.

AB - 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.

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

Abstract

ASJC Scopus subject areas

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