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Titolo:
ENANTIOSELECTIVE COMPLEXATION OF CARBOHYDRATE OR CROWN-ETHER HOSTS WITH ORGANIC AMMONIUM ION GUESTS DETECTED BY FAB MASS-SPECTROMETRY
Autore:
SAWADA M; OKUMURA Y; SHIZUMA M; TAKAI Y; HIDAKA Y; YAMADA H; TANAKA T; KANEDA T; HIROSE K; MISUMI S; TAKAHASHI S;
Indirizzi:
OSAKA UNIV,INST SCI & IND RES IBARAKI OSAKA 567 JAPAN
Titolo Testata:
Journal of the American Chemical Society
fascicolo: 16, volume: 115, anno: 1993,
pagine: 7381 - 7388
SICI:
0002-7863(1993)115:16<7381:ECOCOC>2.0.ZU;2-O
Fonte:
ISI
Lingua:
ENG
Soggetto:
FAST-ATOM-BOMBARDMENT; ALKALI-METAL-IONS; GAS-PHASE; CHIRAL RECOGNITION; CATION COMPLEXES; SEMIEMPIRICAL CALCULATIONS; ABSOLUTE-CONFIGURATION; INCLUSION COMPLEXES; METHYL GLYCOSIDES; PODAND IONOPHORES;
Tipo documento:
Article
Natura:
Periodico
Settore Disciplinare:
Science Citation Index Expanded
Citazioni:
115
Recensione:
Indirizzi per estratti:
Citazione:
M. Sawada et al., "ENANTIOSELECTIVE COMPLEXATION OF CARBOHYDRATE OR CROWN-ETHER HOSTS WITH ORGANIC AMMONIUM ION GUESTS DETECTED BY FAB MASS-SPECTROMETRY", Journal of the American Chemical Society, 115(16), 1993, pp. 7381-7388

Abstract

Enantioselective host-guest complexation has been demonstrated by FABmass spectrometry. Among several carbohydrates, a modified beta-mannofuranoside 6b as well as chiral crown ethers 10 and 13, differentiatesa chiral ammonium ion guest such as the (1-(1-naphthyl)ethyl)ammoniumion. The relative peak intensity (RPI) method has been applied to theevaluation of such diastereomcric complex ions where the peak intensity of the target host (M)-guest (A+) complex ion I((M+A)+) is comparedto 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 examinationsand 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.

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Documento generato il 06/07/20 alle ore 05:17:30