Synthesis of Diketopiperazine and its Analogs
Mentor 1
Dr. Mahmun M. Hossain
Location
Union Wisconsin Room
Start Date
28-4-2017 1:30 PM
End Date
28-4-2017 4:00 PM
Description
Anticancer drug synthesis is a lengthy and expensive process with a numerous number of steps. Currently, most synthetic procedures for these drugs are hugely expensive and low yielding. The goal of this project is to develop new organic reactions and create the most cost and time effective synthetic routes. I have been working on synthesizing the first three steps of Tryprostatin. Tryprostatin is an inhibitor of microtubule assembly which is a process that all cancers must undergo to receive blood and nutrients from their host. This is an essential process for cancer growth and using Tryprostatin in conjunction with other drugs could make for an effective treatment. Our synthesis starts out with an amino acid salt (glycine ethyl ester hydrochloride), a readily available and cheap compound which is converted by various transformations to Tryprostatin. My task was to synthesize the three initial steps in the synthesis of Tryprostatin which are: the coupling reaction of F-moc Proline-OH with an amino acid salt, deprotection of F-moc and cyclization to get hexahydropyrrolo [1,2-a] pyrazine-1,4-dione, and the Boc protection of hexahydropyrrolo [1,2-a] pyrazine-1,4-dione. After completing each reaction, I identified my compounds with various techniques such as thin-layer chromatography, NMR spectroscopy, and mass spectrometry. I also used various purification techniques such as extraction, column chromatography, and recrystallization. I have been able to successfully synthesize the initially two steps of our synthetic route of producing Tryprostatin. This result is a stepping stone and encouragement in further pursuing our goal of producing a cost and time effective synthetic route.
Synthesis of Diketopiperazine and its Analogs
Union Wisconsin Room
Anticancer drug synthesis is a lengthy and expensive process with a numerous number of steps. Currently, most synthetic procedures for these drugs are hugely expensive and low yielding. The goal of this project is to develop new organic reactions and create the most cost and time effective synthetic routes. I have been working on synthesizing the first three steps of Tryprostatin. Tryprostatin is an inhibitor of microtubule assembly which is a process that all cancers must undergo to receive blood and nutrients from their host. This is an essential process for cancer growth and using Tryprostatin in conjunction with other drugs could make for an effective treatment. Our synthesis starts out with an amino acid salt (glycine ethyl ester hydrochloride), a readily available and cheap compound which is converted by various transformations to Tryprostatin. My task was to synthesize the three initial steps in the synthesis of Tryprostatin which are: the coupling reaction of F-moc Proline-OH with an amino acid salt, deprotection of F-moc and cyclization to get hexahydropyrrolo [1,2-a] pyrazine-1,4-dione, and the Boc protection of hexahydropyrrolo [1,2-a] pyrazine-1,4-dione. After completing each reaction, I identified my compounds with various techniques such as thin-layer chromatography, NMR spectroscopy, and mass spectrometry. I also used various purification techniques such as extraction, column chromatography, and recrystallization. I have been able to successfully synthesize the initially two steps of our synthetic route of producing Tryprostatin. This result is a stepping stone and encouragement in further pursuing our goal of producing a cost and time effective synthetic route.
