EnantioselectivePhotolysis and Quantitative Chiral Analysis of Tryptophan Complexed With Alkali‐Metalized L‐Serine in the Gas Phase. Issue 5 (1st April 2015)

• Record Type: Journal Article
• Authors: Fujihara, Akimasa; Maeda, Naoto; Hayakawa, Shigeo
• Is Part Of: Chirality. Volume 27:Issue 5(2015)
• Page Start: 349
• Page End: 352
• Publication Date: 2015-04-01
• Subjects: Chirality -- Periodicals; Pharmaceutical chemistry -- Periodicals; 541.22
• DOI: 10.1002/chir.22442
• Languages: English
• ISSNs: 0899-0042

Abstract

<abstract abstract-type="main"> <title>Abstract</title> <p>The <named-content content-type="reactionType" xlink:type="simple" xmlns:xlink="http://www.w3.org/1999/xlink">enantioselective</named-content><named-content content-type="reactionType" xlink:type="simple" xmlns:xlink="http://www.w3.org/1999/xlink">photolysis</named-content> of a cold gas‐phase noncovalent complex of tryptophan with alkali‐metalized L‐serine, M<sup>+</sup>(L‐Ser)(Trp) (M = Na and Li), was examined using a tandem mass spectrometer containing a variable‐temperature ion trap. CO<sub>2</sub> loss from Trp in the clusters was enantiomerically selective in ultraviolet excitation with linearly polarized light. M<sup>+</sup>(L‐Ser) promoted the <named-content content-type="reactionType" xlink:type="simple" xmlns:xlink="http://www.w3.org/1999/xlink">enantioselective</named-content><named-content content-type="reactionType" xlink:type="simple" xmlns:xlink="http://www.w3.org/1999/xlink">photolysis</named-content> of Trp as a chiral auxiliary. The <named-content content-type="reactionType" xlink:type="simple" xmlns:xlink="http://www.w3.org/1999/xlink">enantioselective</named-content><named-content content-type="reactionType" xlink:type="simple" xmlns:xlink="http://www.w3.org/1999/xlink">photolysis</named-content> of the D‐enantiomer was applied to a quantitative chiral analysis, in which the optical purity of tryptophan could be determined by measuring the relative abundance ratio <italic>R</italic> of the <named-content content-type="reactionType" xlink:type="simple" xmlns:xlink="http://www.w3.org/1999/xlink">enantioselective</named-content> CO<sub>2</sub> loss to the chiral‐independent evaporation of L‐Ser in a single photodissociation mass spectrum of M<sup>+</sup>(L‐Ser)(Trp). <italic>Chirality 27:349–352, 2015</italic>. © 2015 Wiley Periodicals, Inc.</p> </abstract>