Infrared spectroscopic confirmation of [alpha]-lactone formation in the dissociation of a gaseous amino acid

The product obtained upon collision-induced dissociation of sulfonated phenylalanine in the gas phase has been investigated by using infrared multiphoton dissociation spectroscopy with a free-electron laser. This confirms that the product formed by loss of ammonia from the amino acid is the [alpha]-...

Full description

Saved in:
Bibliographic Details
Published in:Journal of physical organic chemistry 2017-02, Vol.30 (2)
Main Authors: Wenthold, Paul G, Koirala, Damodar, Somogyi, Arpad, Poutsma, J C
Format: Article
Language:English
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:The product obtained upon collision-induced dissociation of sulfonated phenylalanine in the gas phase has been investigated by using infrared multiphoton dissociation spectroscopy with a free-electron laser. This confirms that the product formed by loss of ammonia from the amino acid is the [alpha]-lactone, as had been deduced previously based on qualitative analysis and electronic structure calculations. Spectroscopically, the structure is confirmed by the presence of the carbonyl stretching peak at 1915cm-1 and supported by excellent agreement between the predicted and observed S-O stretching bands. The agreement between predicted relative intensities is not as good, but can be attributed to the nonlinear process of IRMPD. Copyright © 2016 John Wiley & Sons, Ltd.
ISSN:0894-3230
1099-1395
DOI:10.1002/poc.3606