Direct screening of chiral discrimination abilities of chiral hosts using mass spectrometry.
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.
Shizuma
Motohiro
M
Department of Biochemistry, Osaka Municipal Technical Research Institute, Morinomiya, Joto-ku, Osaka 5368553, Japan. shizuma@omtri.city.osaka.jp
Adachi
Hiroshi
H
Ono
Daisuke
D
Sato
Hirofumi
H
Nakamura
Masaki
M
D001592:Benzyl Alcohols / Q000737:chemistry; D045424:Complex Mixtures / Q000032:analysis* / Q000302:isolation & purification; D003903:Deuterium / Q000737:chemistry; D004987:Ethers / Q000737:chemistry; D005026:Ethylene Glycols / Q000737:chemistry; D013058:Mass Spectrometry; D013194:Staining and Labeling; D013237:Stereoisomerism; D013379:Substrate Specificity
D001592:Benzyl Alcohols; D045424:Complex Mixtures; D004987:Ethers; D005026:Ethylene Glycols; C013484:diethylene glycol; D003903:Deuterium; C046886:3-nitrobenzyl alcohol