Presentation Title

Synthesis of Unnatural Amino Acids Using a Chiral Auxiliary

Faculty Mentor

Jeffrey Cannon

Start Date

18-11-2017 12:30 PM

End Date

18-11-2017 1:30 PM

Location

BSC-Ursa Minor 140

Session

Poster 2

Type of Presentation

Poster

Subject Area

physical_mathematical_sciences

Abstract

Abstract: Amino acids comprise a family of ubiquitous molecules that achieve a variety of functions in all living organisms. The goal of this study is to find a straightforward synthesis of unnatural amino acids (UAAs) with the aid of a stereochemistry-directing auxiliary, known as the Ellman auxiliary. Utilizing enolate alkylation techniques to generate amino acids that contain unique side chains necessary for biological activity serves as a proof of concept for the ability to create these unnatural products in a stereocontrolled manner. From here, the pathway may be simplified using the Ireland–Claisen rearrangement, one of the most effective carbon–carbon bond formation reactions in organic chemistry. Thus far, this work has produced high yields via the enolate reaction with tolerance for multiple electrophiles and functional groups. This proven chemistry will allow for testing the scope of this reaction with a larger array of electrophiles in order to test the breadth of application for this specific alkylation process. Future studies will seek to discover the range of product possibilities and functional group tolerance that this synthesis will allow. Additionally, currently ongoing investigation of the Ireland–Claisen rearrangement will provide a reliable, fast, and stereospecific synthetic route. This process could streamline the development of amino acids that are not encoded naturally by DNA and can be used downstream in the development of new pharmaceuticals.

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Nov 18th, 12:30 PM Nov 18th, 1:30 PM

Synthesis of Unnatural Amino Acids Using a Chiral Auxiliary

BSC-Ursa Minor 140

Abstract: Amino acids comprise a family of ubiquitous molecules that achieve a variety of functions in all living organisms. The goal of this study is to find a straightforward synthesis of unnatural amino acids (UAAs) with the aid of a stereochemistry-directing auxiliary, known as the Ellman auxiliary. Utilizing enolate alkylation techniques to generate amino acids that contain unique side chains necessary for biological activity serves as a proof of concept for the ability to create these unnatural products in a stereocontrolled manner. From here, the pathway may be simplified using the Ireland–Claisen rearrangement, one of the most effective carbon–carbon bond formation reactions in organic chemistry. Thus far, this work has produced high yields via the enolate reaction with tolerance for multiple electrophiles and functional groups. This proven chemistry will allow for testing the scope of this reaction with a larger array of electrophiles in order to test the breadth of application for this specific alkylation process. Future studies will seek to discover the range of product possibilities and functional group tolerance that this synthesis will allow. Additionally, currently ongoing investigation of the Ireland–Claisen rearrangement will provide a reliable, fast, and stereospecific synthetic route. This process could streamline the development of amino acids that are not encoded naturally by DNA and can be used downstream in the development of new pharmaceuticals.