Title

Synthesis of Uncommon 6,6-linked Disaccharides Analogs

Poster Number

20

Lead Author Major

Biochemistry and Pre-Dentistry/Biological Sciences

Format

Poster Presentation

Faculty Mentor Name

Andreas H. Franz

Faculty Mentor Department

Chemistry

Abstract/Artist Statement

Unexplored disaccharide analogs for future studies of their biological functions as glycosidase inhibitors were investigated. In particular, uncommon 6,6-linked disaccharide analogs bound by ester, thioester, and amide functional groups were prepared and characterized. Synthesis of the 6,6 ester linked disaccharide was performed via a Lewis acidpromoted ring opening of tri-O-acetyl-β- glucopyranurono-6,1-lactone using benzyl-2,3,4- tri-O-benzyl-ß-D-glucopyranose as the nucleophile. The 6,6 thioester linked disaccharide was attempted by converting 1,2,3,4-tetra-O-benzyl-ß-D-glucopyranose into 1,2,3,4-tetra-O-benzyl-ß-6-thioester Dglucopyranose under Mitsonobu reaction conditions. Synthesis of amide linked disaccharides was also attempted by attacking 1,2,3,4-tetra-O-benzyl- ß-D-glucuronic acid with 1,2,3,4-tetra-O-benzyl- 6-amino-ß-Dglucopyranose. The resulting products were analyzed and characterized using ElectroSpray Ionization (ESI) mass spectrometry and Nuclear Magnetic Resonance (NMR) spectroscopy.

Location

DeRosa University Center, Ballroom

Start Date

30-4-2016 1:30 AM

End Date

30-4-2016 3:30 PM

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Apr 30th, 1:30 AM Apr 30th, 3:30 PM

Synthesis of Uncommon 6,6-linked Disaccharides Analogs

DeRosa University Center, Ballroom

Unexplored disaccharide analogs for future studies of their biological functions as glycosidase inhibitors were investigated. In particular, uncommon 6,6-linked disaccharide analogs bound by ester, thioester, and amide functional groups were prepared and characterized. Synthesis of the 6,6 ester linked disaccharide was performed via a Lewis acidpromoted ring opening of tri-O-acetyl-β- glucopyranurono-6,1-lactone using benzyl-2,3,4- tri-O-benzyl-ß-D-glucopyranose as the nucleophile. The 6,6 thioester linked disaccharide was attempted by converting 1,2,3,4-tetra-O-benzyl-ß-D-glucopyranose into 1,2,3,4-tetra-O-benzyl-ß-6-thioester Dglucopyranose under Mitsonobu reaction conditions. Synthesis of amide linked disaccharides was also attempted by attacking 1,2,3,4-tetra-O-benzyl- ß-D-glucuronic acid with 1,2,3,4-tetra-O-benzyl- 6-amino-ß-Dglucopyranose. The resulting products were analyzed and characterized using ElectroSpray Ionization (ESI) mass spectrometry and Nuclear Magnetic Resonance (NMR) spectroscopy.