Rapid enantiomeric determination of α-hydroxy acids by electrospray ionization tandem mass spectrometry

Peer Reviewed: Chiral analysis by MS

“…Applications are already wide-ranging (18,19,(22)(23)(24) and useful for recognition and quantitative determination of various chiral molecules, such as amino acids, dipeptides, ␣-hydroxy acids, atenolol, propranolol, carbohydrates, norepinephrine, DOPA, and isoproterenol. Extensions to new classes of analytes and metal ions, including Au(I), Pd(II), and Ca(II), are of interest, in addition to the work underway on Ni(II), Fe(II), Zn(II), Cu(II), and Co(II).…”

Stereoselectivity in the collision-activated reactions of gas phase salt complexes

“…These differences can be exploited (i.e., by comparison to data for known standards) and used to determine the enantiomeric purity of a sample. Cooks [3][4][5][6][7][8][9][10][11][12][13][14][15][16], Dearden , , Speranza [27][28][29][30][31][32][33][34][35], and others have provided useful examples of this approach to stereochemical analysis.Along with methods for analyzing the enantiomeric purity of products, there is a growing need for the development of new reaction processes that are stereoselective. In general, these processes have been probed in the condensed phase, but there is no reason why mass spectrometry could not also be used to screen gas phase reactions for stereoselectivity [35,36].…”

“…These differences can be exploited (i.e., by comparison to data for known standards) and used to determine the enantiomeric purity of a sample. Cooks [3][4][5][6][7][8][9][10][11][12][13][14][15][16], Dearden , Lebrilla [21][22][23][24][25][26], Speranza [27][28][29][30][31][32][33][34][35], and others have provided useful examples of this approach to stereochemical analysis.…”

Quantitative determination of the enantiomeric composition of panthotenic acid solutions: a mass spectrometry experiment

“…It is possible to group the methods used for chiral recognition and for quantification of enantiomeric excess by mass spectrometry into four wide types: (a) generation of hostguest diasteromeric adducts using a chiral guest; 4,5 (b) determination of rates of ion/molecule reactions between an enantiomeric guest and a host molecule; 6 (c) collisioninduced dissociation (CID) of diasteromeric adducts in a MS/MS experiment; 7 (d) utilization of the kinetic method [8][9][10][11][12] to quantify the MS/MS chiral effect. 13 This last methodology has been successfully applied to quantitative analysis of aminoacids, 13,14 α-hydroxyacids, 15 sugars 16 and some drugs [17][18][19] and has been shown to be fast and to require very small amounts of sample.…”

“…These references were chosen since (a) they can be easily obtained in enantiomerically pure form; and (b) in previous studies, some of these compounds proved to be useful as reference compounds in chiral analysis. 15,17,18 Four divalent metal cations (M = Ca 2+ , Cu 2+ , Ni 2+ , Zn 2+ ) were selected as the central metal ions owing to their well-known ability to form complexes with oxygen and nitrogencontaining compounds, as well as to their recent use in chiral analysis of several compounds by the kinetic method. 13,[15][16][17][18][19] …”