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Date Permissions Signed

11-23-2021

Date of Award

Fall 2021

Document Type

Masters Thesis

Department or Program Affiliation

Chemistry

Degree Name

Master of Science (MS)

Department

Chemistry

First Advisor

Murhpy, Amanda R.

Second Advisor

Larsen, Michael B.

Third Advisor

Vyvyan, James R.

Abstract

Suzuki-Miyaura cross-coupling reactions were used to modify the tyrosine residues on Bombyx mori silkworm silk proteins using a water-soluble palladium catalyst. Utilizing this cross-coupling reaction, molecules with specific functions can be introduced to silk in order to broaden the capabilities of silk proteins in biological systems. Model reactions using tyrosine derivatives were first screened to optimize reaction conditions. For these reactions, a variety of aryl boronic acids, solvents, buffers and temperature ranges were explored. Qualitative information on the reaction progress was collected via high performance liquid chromatography (HPLC), mass spectrometry (MS) and nuclear magnetic resonance (NMR). Reactions were then applied to silk proteins. Iodination and cross-coupling modifications of silk were characterized with NMR, UV-vis, ion-exchange chromatography (IEC) and infrared spectroscopy (IR). Overall, the research demonstrates the ability to modify silk fibroin using Suzuki-Miyaura reactions following successful iodination of the protein.

Type

Text

Keywords

silk protein, aqueous Suzuki-Miyaura, palladium-mediated, tyrosine

Publisher

Western Washington University

OCLC Number

1287024951

Subject – LCSH

Proteins--Chemical modification; Silk; Paladium catalysts

Format

application/pdf

Genre/Form

masters theses

Language

English

Rights

Copying of this document in whole or in part is allowable only for scholarly purposes. It is understood, however, that any copying or publication of this document for commercial purposes, or for financial gain, shall not be allowed without the author’s written permission.

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