The Organic Synthesis Program supports Professor Daniel J. O'Leary, of the Department of Chemistry at Pomona College, with a Research in Undergraduate Institutions award for his studies of the synthesis and conformational analysis of novel carbohydrate and polypeptide structures. Working with undergraduate researchers, Professor O'Leary investigates the pattern of hydrogen bonding networks in partially isotopically exchanged diols designed to form intramolecular hydrogen bonds, using NMR isotopic perturbation techniques and appropriate theoretical analysis to reveal hydrogen bonds and their arrays. In order to probe the extent to which long-range interactions help stabilize or destabilize carbohydrate conformations in solution, Professor O'Leary synthesizes oligosaccharides as models for hyaluronic acid and examines their conformational preferences. Synthesis of carbocyclic analogs of malformin A1, a bicyclic pentapeptide containing a cyclo-cystine structural element, helps to address the unusual conformational behavior of this naturally occurring substance. Professor Daniel J. O'Leary, of the Department of Chemistry at Pomona College, is supported by the Organic Synthesis Program with a Research in Undergraduate Institutions award for his studies of the three-dimensional shapes (conformations) of biologically relevant molecules in solution. Through the synthesis of comparatively simple model compounds and the use of nuclear magnetic resonance techniques, Professor O'Leary probes the factors controlling the specific shapes adopted by these molecules and, by inference, the larger molecules for which they serve as models. These studies, carried out by undergraduate researchers, are expected to answer questions regarding the effects of various groupings of atoms within molecules on their conformational behavior, an issue of fundamental importance in a wide range of fields, from biology to physical chemistry.
