The use of natural and unnatural amino acids has many applications, some of which include mutagenesis, drug design and delivery, and tissue engineering. However, there is a challenge in their efficient creation. One synthetic method relies on metal complexation of a glycine Schiff’s Base to protect the amino and carboxyl groups of the glycine. While there have been a number of modifications of the ligand system employed by this method, recent alterations have included the incorporation of various electron withdrawing groups. These alterations are hypothesized to increase the acidity of the C-H bond on the α-carbon of the glycine, thus allowing for milder conditions thus increasing the generality and efficiency of the method. To test this hypothesis, a series of glycine metal complexes have been synthesized. Challenges in the method development process will be discussed in detail. The results of the changes in pKa with the addition of electron withdrawing groups to the metal complexed Schiff’s Base of glycine by spectroscopic methods will be presented.

Spectroscopic methods of analysis for the determination of the pKa’s of glycine metal complexes

ACS Spring 2022

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