Studies in Organic Synthesis and Conformational Analysis

Pomona College, Claremont CA

Investigators

Abstract

With this Research at Undergraduate Institutions award, the Organic and Macromolecular Chemistry Program provides renewed support for the research of Professor Daniel J. O'Leary, of the Department of Chemistry at Pomona College. Professor O'Leary will carry out a number of synthetic and conformational studies, addressing issues of hydrogen bonding and polypeptide conformation. Isotopic perturbation techniques for hydrogen bond detection by NMR will be applied to the analysis of arrays of hydrogen bonds involving hydroxyl groups, and the utility of tritium NMR for detecting OH/OH hydrogen bonds will be assayed. The possibility of using hydrogen bond-mediated scalar couplings to assign the relative stereochemistry of acyclic 1,3-diols will be explored, and analysis of isotopic perturbation of the rotameric distribution of methyl groups in compounds supporting N--DH2C interactions may lead to direct NMR techniques for the configurational assignment of chiral methyl groups (R-CHDT). Solution conformations of conformationally constrained polypeptides and their unconstrained analogs will be analyzed for cross-linked 3/10 helical peptides synthesized via an olefin metathesis approach. With the support of a Research at Undergraduate Institutions award from the Organic and Macromolecular Chemistry Program, Professor Daniel J. O'Leary, of the Department of Chemistry at Pomona College, is carrying out a program of synthesis and analytical methods to study hydrogen bonds and other novel weak inter- and intramolecular interactions. Water is the fundamental biological solvent, and proteins, nucleic acids, and sugars are the three fundamental biopolymers. All three rely on hydrogen bonds and directed non-covalent interactions to attain their optimal structures. Understanding the nature of the interactions that control their structures is of fundamental importance, and forms the basis of Professor O'Leary's studies, which are carried out with undergraduate students under this Research at Undergraduate Institutions award.