Intramolecular Hydrogen Bonds in Hydroxy Acids.

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Hydroxy acids are compounds of considerable interest due to their occurence and function in living species. Glycolic acid, for instance, is an important intermediate in the photorespiratory carbon oxidation cycle in higher plants and algae; gamma-hydroxybutyric acid is one of the few compounds that are able to pass the barrier between blood and brain and has been detected in the brain of mammals, where it is synthetisized and used for neuromodulatory purposes. Polymers of glycolic acid or copolymers of glycolic acid and lactic acid are biodegradable and utilized in medicine for absorbable sutures, as carriers for drug delivery systems, and for prostheses.

In the context of the present studies (FWF-projects P8053 and P9095), hydroxy acids were of interest mainly in comparison with the corresponding omega-amino acids. The primary focus was on the various intramolecular interactions, which were studied via quantum chemical ab initio calculations.

The following pages give selected results of glycolic acid, beta-hydroxypropionic acid, gamma-hydroxybutyric acid, and delta-hydroxypentanoic acid. Each page is devoted to a single hydroxy acid and contains several illustrative pictures of relevant conformers. Although most of the information is contained in the text, so that a text-only browser is basically sufficient, these pictures will help in understanding. Therefore, if your browser can load pictures, you might want to turn that option on. The bottom of each page provides links for forward and backward browsing and, in the center entry, an interface to the literature data base of the Institute of Physical and Theoretical Chemistry. Activation of this interface produces an up-to-date list of publications and theses that relate to the specific compound.

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