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Synthesis and Chiral Recognition of Optically Active Isocyanurate Having Amino Acid Units.

Accession number;99A0228200

Title;Synthesis and Chiral Recognition of Optically Active Isocyanurate Having Amino Acid Units.

Author; SUGIMOTO HIROSHI (Sci. Univ. of Tokyo, Fac. of Eng.) YAMANE YUKA (Sci. Univ. of Tokyo, Fac. of Eng.) INOUE SHOHEI (Sci. Univ. of Tokyo, Fac. of Eng.)

Journal Title;Abstracts. Symposium on Biofunctional Chemistry

Journal Code:L0836A

ISSN:

VOL.13th;NO.;PAGE.34-36(1998)

Figure&Table&Reference;

Pub. Country;Japan

Language;Japanese

Abstract;The novel optically active isocyanurate was synthesized from tris(2-carboxyethyl) isocyanurate and L-leucine methyl ester by the amide bond formation. The interaction between the isocyanurate and binaphthol was evaluated by 1H-NMR spectroscopy. In the spectrum of the isocyanurate and racemic binaphthol at the molar ratio of 2:3 in CDCl3, the signal assignable to the OH groups of binaphthol shifted downfield from that of binaphthol alone (.DELTA. 5.0ppm) and splitted in two singlets (.DELTA. 5.5 and 5.6ppm). On the other hand, in the spectrum of the isocyanurate and R-binaphthol, a signal appeared at .DELTA. 5.5ppm. Consequently, optically active isocyanurate is considered to discriminate the enantiomers of binaphthol. In sharp contrast, the 1H-NMR spectrum of methoxycarbonyl-L-leucine methyl ester and racemic binaphthol showed a signal at .DELTA. 5.3ppm. These results indicate that it is necessary for three L-leucine units to be organized on isocyanurate ring in order to recognize the enantiomers of binaphthol separately. (author abst.)

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