Dr. Gregory Friestad
Participation year
Project title

Synthesis of Tetrafibricin: C27-C40 Fragment


The platelet glyocoprotein (GP) IIb/IIIa is the site where tetrafibricin, a GPIIb/IIIa inhibitor, causes conformational changes to prevent platelet aggregation. Tetrafibricin is special for the fact that it is non-peptidic and therefore inhibits platelet aggregation more effectively than peptidic inhibitors. It will help cure various types of heart disease. The purpose of this research is to synthesize the C27-C40 fragment of Tetrafibricin using a series of chemical reactions such as Williamson ether synthesis, Swern oxidation, Julia coupling, nucleophilic addition of nitriles, DIBAL-H reduction and more. The first step of doing this is to take 1, 3-propanediol and protect one of its alcohols with p-methoxybenzyl chloride (PMBCI). The reaction was then worked up, the final product, 1-[(4-Methoxybenzyl) oxy]-3-propanol, was identifies by TLC and then collected using column chromatography. The Infrared Spectrum was taken to identify the compound. The Swern oxidation of the alcohol in, 1-[(4-Methoxybenzyl) oxy]-3-propanol to the aldehyde is still in progress and results have not been obtained. One of our near future goals is to synthesize the C35-C38 fragment and ultimately build up to the C27-C40 fragment.

Alfredo  Garcia
University of Iowa