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Tetrahedron Lett. 2010 Jul 21;51(29):3724-3727.

Design and Synthesis of Functionalized Trisaccharides as p53-Peptide Mimics.

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1
Department of Chemistry and Chemical Biology, Harvard University, 12 Oxford St., Cambridge, MA and Department of Biological Cellular and Molecular Pharmacology, Harvard Medical School, Longwood, Boston, MA.

Abstract

Oligosaccharides represent potentially useful scaffolds for the development of peptidomimetics. We report here the design and synthesis of functionalized trisaccharides modeled after an α-helical 15-mer peptide region of p53 which binds to its cellular regulator MDM2. The trisaccharide scaffold was obtained efficiently by applying the sulfoxide glycosylation reaction as a key methodology.

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