Bioinspired Chemical Approach for Synthesis of Allysine Pubblico
Shahin, Sophia (Spring 2024)
Abstract
In this study, we present a novel chemical method for synthesizing allysine, an aldehyde containing posttranslational modification catalyzed by lysyl oxidase. This chemistry offers the ability to selectively oxidize the side chain of dimethyl lysine to allysine. Through numerous linear and cyclic peptide examples, we demonstrate the high chemoselectivity this chemical method offers, portraying its broad utility. We also expanded this chemical method for use on tertiary amine- containing small molecules. To demonstrate the applications of our method, we diversified bioactive peptides with various affinity tags and fluorescent dyes. Finally, we showcase the potential of this method for developing cellular models for studying allysine-associated diseases.
Table of Contents
Introduction.....................................................................................................................1
Results and Discussion......................................................................................................6
Chapter 1: Background, inspiration, and approach................................................6
Chapter 2: Substrate scope of synthesizing allysine in linear and cyclic peptides...13
Chapter 3: Substrate scope for modification of small molecules...........................16
Chapter 4: Late-stage diversification of peptides via allysine with varying tags.....19
Chapter 5: Synthesis of allysine on solid support................................................20
Chapter 6: Cellular imaging applications of TACO reaction..................................23
Conclusion and Future Directions....................................................................................26
Acknowledgment of Contributions...................................................................................27
References......................................................................................................................28
Supplemental Information...............................................................................................30
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