113858-79-0Relevant articles and documents
Enantioselective complexation of carbohydrate or crown ether hosts with organic ammonium ion guests detected by FAB mass spectrometry
Sawada, Masami,Okumura, Yasuo,Shizuma, Motohiro,Takai, Yoshio,Hidaka, Yukio,Yamada, Hitoshi,Tanaka, Takanori,Kaneda, Takahiro,Hirose, Keiji,Misumi, Soichi,Takahashi, Shigetoshi
, p. 7381 - 7388 (1993)
Enantioselective host-guest complexation has been demonstrated by FAB mass spectrometry. Among several carbohydrates, a modified β-mannofuranoside 6b as well as chiral crown ethers 10 and 13, differentiates a chiral ammonium ion guest such as the (1-(1-naphthyl)ethyl)ammonium ion. The relative peak intensity (RPI) method has been applied to the evaluation of such diastereomeric complex ions where the peak intensity of the target host (M)-guest (A+) complex ion I((M+A)+) is compared to that of the internal standard host (R)-guest (A+) ion I((R+A)+): the RPI value = I((M+A)+)/I((R+A)+). The present enantioselectivity is characterized by the RPI ratio value I((M+A(R))+)/I((M+A(S))+) in the range 1.2-1.6 (1.0 ± 0.1 nonenantioselectivity). The observed preference of the (R)-enantiomer guest is compatible with model examinations and related coloration results. With chiral crown ether 13, a close correspondence exists between the FABMS/RPI enantioselection and that of strictly related solution-phase energetics in association equilibria. The usefulness of the RPI method is also shown by comparison to the relevant equilibrium constants (NMR titration) in solution.