Title

Synthesis and NMR Characterization of Oligoresorcinol Precursors

Lead Author Major

Biochemistry

Lead Author Status

Junior

Format

Poster Presentation

Faculty Mentor Name

Andreas Franz

Faculty Mentor Department

Chemistry

Graduate Student Mentor Name

Tre Andang

Graduate Student Mentor Department

Chemistry

Abstract/Artist Statement

The structure of the DNA double helix has drawn growing interest to many researchers since it has been discovered. My research focuses on the synthesis of precursors of oligoresorcinols, which have been found to form double helices in water. Resorcinol, a meta-isomer of benzenediol, is an organic compound that is a white, water-soluble solid. Clinically, it is used in the treatment of skin disorders and infections such as acne, dermatitis, eczema, and warts.[1] Oligoresorcinols are multiple resorcinols attached to each other to form a long strand. The double-helical oligoresorcinols formed in water can be unwound by β-cyclodextrin (β-CD), which results in single strands of oligoresorcinols.[2] Oligoresorcinols are significant in that they detect oligosaccharides, multiple monosaccharides connected to each other. Not only could this provide insight into the biological functions of saccharides, but it also promotes the development of chemotherapy, since saccharides play essential roles in various cellular activities such as intercellular recognition[3]. Oligoresorcinols recognize oligosaccharides through noncovalent interactions in the water when it forms a double helix, which unravels and entwines upon complexation with specific oligosaccharides with a particular chain length and glycosidic linkage pattern.[4]We will expand on this research by synthesizing different chain lengths of oligoresorcinols and testing their ability to detect different oligosaccharides in water. To achieve this, the Suzuki cross-coupling reaction will be used to synthesize oligoresorcinols. This is a reaction of an organoborane with an organohalide, forming a carbon-carbon bond to give the coupled product while using a palladium catalyst and base. The expected result is that the double-helical oligoresorcinols will be able to detect different types of oligosaccharides in the solution. In the future, NMR will be used to confirm the detection of oligosaccharides by oligoresorcinols.

[1] “Resorcinol.” National Center for Biotechnology Information. PubChem Compound Database, U.S. National Library of Medicine, pubchem.ncbi.nlm.nih.gov/compound/Resorcinol.

[2] Goto, Hidetoshi, et al. “Supramolecular Control of Unwinding and Rewinding of a Double Helix of Oligoresorcinol Using Cyclodextrin/Adamantane System.” Journal of the American Chemical Society 129 (2007): 109–112.

[3] Goto, Hidetoshi, et al. “Supramolecular Control of Unwinding and Rewinding of a Double Helix of Oligoresorcinol Using Cyclodextrin/Adamantane System.” Journal of the American Chemical Society 129 (2007): 109–112.

[4] Goto, Hidetoshi, et al. “Double Helical Oligoresorcinols Specifically Recognize Oligosaccharides via Heteroduplex Formation through Noncovalent Interactions in Water.” Journal of the American Chemical Society 129 (2007): 9168–9174.

Location

Virtual

Start Date

25-4-2020 1:00 PM

End Date

25-4-2020 3:00 PM

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Apr 25th, 1:00 PM Apr 25th, 3:00 PM

Synthesis and NMR Characterization of Oligoresorcinol Precursors

Virtual

The structure of the DNA double helix has drawn growing interest to many researchers since it has been discovered. My research focuses on the synthesis of precursors of oligoresorcinols, which have been found to form double helices in water. Resorcinol, a meta-isomer of benzenediol, is an organic compound that is a white, water-soluble solid. Clinically, it is used in the treatment of skin disorders and infections such as acne, dermatitis, eczema, and warts.[1] Oligoresorcinols are multiple resorcinols attached to each other to form a long strand. The double-helical oligoresorcinols formed in water can be unwound by β-cyclodextrin (β-CD), which results in single strands of oligoresorcinols.[2] Oligoresorcinols are significant in that they detect oligosaccharides, multiple monosaccharides connected to each other. Not only could this provide insight into the biological functions of saccharides, but it also promotes the development of chemotherapy, since saccharides play essential roles in various cellular activities such as intercellular recognition[3]. Oligoresorcinols recognize oligosaccharides through noncovalent interactions in the water when it forms a double helix, which unravels and entwines upon complexation with specific oligosaccharides with a particular chain length and glycosidic linkage pattern.[4]We will expand on this research by synthesizing different chain lengths of oligoresorcinols and testing their ability to detect different oligosaccharides in water. To achieve this, the Suzuki cross-coupling reaction will be used to synthesize oligoresorcinols. This is a reaction of an organoborane with an organohalide, forming a carbon-carbon bond to give the coupled product while using a palladium catalyst and base. The expected result is that the double-helical oligoresorcinols will be able to detect different types of oligosaccharides in the solution. In the future, NMR will be used to confirm the detection of oligosaccharides by oligoresorcinols.

[1] “Resorcinol.” National Center for Biotechnology Information. PubChem Compound Database, U.S. National Library of Medicine, pubchem.ncbi.nlm.nih.gov/compound/Resorcinol.

[2] Goto, Hidetoshi, et al. “Supramolecular Control of Unwinding and Rewinding of a Double Helix of Oligoresorcinol Using Cyclodextrin/Adamantane System.” Journal of the American Chemical Society 129 (2007): 109–112.

[3] Goto, Hidetoshi, et al. “Supramolecular Control of Unwinding and Rewinding of a Double Helix of Oligoresorcinol Using Cyclodextrin/Adamantane System.” Journal of the American Chemical Society 129 (2007): 109–112.

[4] Goto, Hidetoshi, et al. “Double Helical Oligoresorcinols Specifically Recognize Oligosaccharides via Heteroduplex Formation through Noncovalent Interactions in Water.” Journal of the American Chemical Society 129 (2007): 9168–9174.