Chem 242 @ Dickinson

An Amino Acid Primer

Today was the start of Chapter 26, in which we study amino acids and the compounds they make. There was a great deal of factual information today, including some basic nomenclature. We also saw the basic structure of peptides (in which amino acids are strung together in a chain) and made a note on how the peptide bond has limited ability to rotate. Finally, we saw how to draw amino acids as Fischer projections, in the standard biochemist's configuration.

We spent the last part of the lecture looking at how to synthesize amino acids; here we saw a number of familiar reactions including the Hell-Volhard-Zelinski and Gabriel reactions, a variant of the malonate ester synthesis called the amidomalonate synthesis (with alkylation, hydrolysis, and decarboxylation steps) and reductive elimination. The problem with all of these is that the product amino acids are racemic. I showed how to resolve the mixture into separable diastereomers by treatment with a chiral base but you are still wasting half of the product if you do that. On Friday our first subject will be how to create a single chiral center with no waste of materials.

posted by DCChem @ 9:46 AM