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Synthesis and Isolation of an Orthoamide Carbocation Metalloenzyme Mimic Building Block
Poster   Open access

Synthesis and Isolation of an Orthoamide Carbocation Metalloenzyme Mimic Building Block

Emily Twitchell and Megan Brown
University of West Florida Libraries
Summer Undergraduate Research Program (University of West Florida, Pensacola, Florida, 08/2024)
08/2024

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Abstract

Macrocyclic polyamines are important building blocks as ligands for biomimetic chemistry to develop inhibitors that target specific enzymes. Our goal is to synthesize 1,4,8-triazacycloundecane (TACU) (Figure 1), a small molecule mimic of the active site of a Zn(II) containing metalloenzyme, carboxypeptidase A (CPA) (Figure 1).1 In this presentation, we however report the synthesis of a carbocation intermediate (Figure 2) during the TACU synthesis in an attempt to isolate and study its X-ray crystal structure so that we can understand the possible reasons for the low literature-reported yields of 50-60% for TACU.1
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