Event Title

Copper-free Sonogashira Reaction to Modify the Tyrosine Residues on Silk Proteins

Research Mentor(s)

Amanda Murphy

Description

Here we explore the use of a copper-free Sonogashira reaction using a palladium catalyst to modify the tyrosine residues on silkworm silk proteins. Utilizing this cross coupling reaction, alkynes with specific functions can be introduced to silk in order to broaden the capabilities of silk proteins in biological systems. A halogenation reaction to iodinate tyrosine was first developed using the mild iodinating reagent bis(pyridine)iodonium(I) tetrafluoroborate (IPy2BF4). After that, a variety of reaction conditions were explored for the cross-coupling reactions. Qualitative information on the reaction progress collected via X-ray photoelectron spectroscopy (XPS) and infrared spectroscopy (IR) will be presented.

Document Type

Event

Start Date

May 2018

End Date

May 2018

Department

Chemistry

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.

Language

English

Format

application/pdf

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May 16th, 12:00 PM May 16th, 3:00 PM

Copper-free Sonogashira Reaction to Modify the Tyrosine Residues on Silk Proteins

Here we explore the use of a copper-free Sonogashira reaction using a palladium catalyst to modify the tyrosine residues on silkworm silk proteins. Utilizing this cross coupling reaction, alkynes with specific functions can be introduced to silk in order to broaden the capabilities of silk proteins in biological systems. A halogenation reaction to iodinate tyrosine was first developed using the mild iodinating reagent bis(pyridine)iodonium(I) tetrafluoroborate (IPy2BF4). After that, a variety of reaction conditions were explored for the cross-coupling reactions. Qualitative information on the reaction progress collected via X-ray photoelectron spectroscopy (XPS) and infrared spectroscopy (IR) will be presented.