Copper-free Sonogashira Reaction to Modify the Tyrosine Residues on Silk Proteins
Research Mentor(s)
Murphy, Amanda R.
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
Genre/Form
student projects, posters
Subjects – Topical (LCSH)
Palladium catalysts; Silk; Natural products--Synthesis
Type
Image
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
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.