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Catalysts for C-N Bond Formation, Polymers for the Delivery of mRNA, and Metal-Ligand Mediated Mechanical Gradient Formation

  • Author(s): Oldenhuis, Nathan John
  • Advisor(s): Guan, Zhibin
  • Dong, Vy M
  • et al.
Creative Commons Attribution 4.0 International Public License
Abstract

In this dissertation, I will discuss the primary authored papers I have published over my time at UCI. They cover a broad range of topics, including catalysis, drug delivery, and dynamic materials.

Chapter 1 is a modified version of a yet to be published book chapter I have written. It will discuss green methodology for the construction of amide bonds compared to commonly used methods, which generally produce stoichiometric amounts of waste.

Chapter 2 is reproduced from a published manuscript that describes a catalytic system using a PNP type pincher complex, Ru-Macho, which was discovered to produce amides via dehydrogenative coupling of alcohols and amines. This methodology allows for the creation of secondary and tertiary amides as well as imines, producing only hydrogen and water as the by-products.

Chapter 3 is reproduced from a published manuscript that describes a catalytic system using a PNP type pincher complex, Ru-Macho, which was discovered to produce alpha chiral amines via a hydrogen borrowing methodology from secondary alcohols and Ellman’s tert butanesufinylamide. This methodology allows for the creation of high value added alpha chiral amines, producing only water as the by-product.

Chapter 4 is reproduced from a published manuscript that describes the development of a dendronized polymer system for the delivery of mRNA to immortalized and primary cells in vitro. In the past decade mRNA delivery has emerged as a promising way to modulate protein expression without the need for plasmid DNA transfections. In spite of this need, there are very few synthetic vectors currently available for mRNA delivery. We developed a vector, which was able to deliver both eGFP and Luc-2 mRNA to 3T3, DC 2.4, and bone marrow derived dendritic cells.

Chapter 5 is a yet to be published manuscript which, describes the formation of a biomimetic synthetic mechanical gradient material. Large changes in material stiffness at interfaces often causes manifestation of damage at the interface during stressing of the material. In order to solve this problem, we have developed a synthetic mechanical gradient material based of the metal ligand interaction found in the polychaete worm jaw. Using metal imidazole based materials previously studied in the lab, we were able to create a material with a continuous metal gradient of over 2 orders of magnitude in Young’s modulus.

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