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Direct screening of chiral discrimination abilities of chiral hosts using mass spectrometry
Author(s) -
Shizuma Motohiro,
Adachi Hiroshi,
Ono Daisuke,
Sato Hirofumi,
Nakamura Masaki
Publication year - 2009
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/chir.20586
Subject(s) - chemistry , diastereomer , enantiomer , deuterium , chiral derivatizing agent , enantiomeric excess , mass spectrum , diethylene glycol , chiral column chromatography , racemic mixture , isopropyl , mass spectrometry , chromatography , stereochemistry , organic chemistry , enantioselective synthesis , ethylene glycol , catalysis , physics , quantum mechanics
A simultaneous estimation of the chiral discrimination abilities of several chiral hosts was demonstrated on the basis of one mass spectrum. The chiral host mixture, including H 1 , H 2 , H 3 ···, and H m (m: number of hosts) was prepared by etherification of several chiral alcohols with bistosylate of diethylene glycol. An equimolar mixture of a deuterium‐labeled ( S )‐ and unlabeled ( R )‐enantiomer of an amino acid isopropyl ester hydrochloride (G S ‐dn + Cl − and G R + Cl − , n: number of deuterium atoms) was added to the chiral host mixture, and the FAB mass spectrum was measured to evaluate the chiral discrimination ability of each host in the mixture without isolation. The chiral discrimination ability of each host toward the guest is represented by the relative peak intensity of the diastereomeric complex ion pair, I (H m + G R ( + / I (H m + G S ‐dn ) + (= I R /I S‐dn value). Several new hosts showed good chiral discrimination toward the guest. Chirality, 2009. © 2008 Wiley‐Liss, Inc.