Title

Synthesis of a Benzoboroxole for the Molecular Recognition of Carbohydrates

Faculty Sponsor

Dr. Kevin Jantzi

College

Arts and Sciences

Department/Program

Chemistry

ORCID Identifier(s)

Agnel Rahul Rayan

Document Type

Poster Presentation

Celebration Date

Summer 7-28-2015

Abstract

Synthesis of boronolectins as a sensor for the recognition of carbohydrates in vivo has significant applications in biochemical and biomedical science. Modern techniques for recognition of carbohydrates in vivo no longer rely on non-covalent interactions like hydrogen bonding, with the target, due to the competition of the sensor with both target and the excess of water in the living system. The first step of the synthesis, the reaction between glycine methyl ester and methyl amine for the formation of glycine methyl amide, was achieved with an 89% yield. The second step of the synthesis was the reaction between the glycine methyl amine and pivalaldehyde in the presence of a catalyst (ytterbium trifalate) for the formation of a lactam. The failure of this reaction was hypothesized to be due to the improper catalyst used. The reaction could be performed better if a Bronsted lowry acid (HCl) was used instead of the lewis acid (ytterbium) to check the viability of the reaction and be able to finish the synthesis.

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