Circular dichroism readout of sugar recognition in the cleft of a fused-pyridine receptor

Shun Ichi Tamaru, Seiji Shinkai, Alisher B. Khasanov, Thomas W. Bell

Research output: Contribution to journalArticle

36 Citations (Scopus)

Abstract

Dicarboxamide host 2 forms 1:1 complexes with n-octyl pyranosides derived from D-glucose, D-mannose, D-galactose, D-fucose, D-lyxose, and D-arabinose. Association constants (Ka) in the range of 77-940 M-1 were measured in chloroform by means of induced circular dichroism and fluorescence spectroscopy. Variations in Ka values correspond qualitatively to expected differences in hydrogen-bonding abilities of guest hydroxyl groups. Induced circular dichroism effects for complexes of saccharides bearing equatorial 3-OH, 4-OH, and 6-OH groups show that the host chromophore is twisted in a P-helical conformation. A structural model is proposed that is also consistent with the results of previous studies involving complexation of dicarboxylic acid 1 with cationic saccharides in methanol.

Original languageEnglish
Pages (from-to)4972-4976
Number of pages5
JournalProceedings of the National Academy of Sciences of the United States of America
Volume99
Issue number8
DOIs
Publication statusPublished - Apr 16 2002

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All Science Journal Classification (ASJC) codes

  • General

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