Synthesis and NMR analysis of intramolecular hydrogen bonding in inositol-based triols and tetrols

CHED 875

Alexander J. Pickrell and Daniel J. O'Leary. Department of Chemistry, Pomona College, 645 North College Avenue, Claremont, CA 91711
Hydrogen bonding plays a vital role in numerous biological and chemical reactions, as well as affecting conformations of various biochemical molecules. Various derivatives of myo-inositol monoorthoformate containing unique 1,3-diaxial intramolecular hydrogen bonding networks have been prepared for NMR analysis. We have synthesized and analyzed a symmetric tetrol as well as a triol containing a network of OH/OH/OH hydrogen bonds. Specifically, titrations have been done in order to measure deuterium isotope effects in the proton NMR spectra. These titrations employ the addition of exchangeable deuterons and the hydrogen-bond mediated isotope effects arise as chemical shift perturbations in the hydroxyl resonances. Our preliminary measurements suggest that this approach can be used to detect a contiguous array of four hydroxyl groups.