Synthesis of a 56 component library of sugar beta-peptides
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Updated: Sep 30, 2026

Split-and-pool Synthesis and Characterization of Peptide Tertiary Amide Library
Published on: June 20, 2014
Anders Lohse1, Frank Schweizer, Ole Hindsgaul
1Department of Chemistry, University of Aarhus, DK-8000 Aarhus C., Denmark.
Abstract:
Many biological processes of vital importance are triggered by the molecular recognition of small carbohydrate units by proteins and receptors thus leading to the belief that carbohydrates could act as candidates for the design of new drugs. We have developed a new useful synthetic approach, which can be applied in a combinatorial manner, giving access to 1,1-di-substituted pyrans projecting amide side chains in both the alpha- and beta-directions. Thus, treatment of the readily accessible hemiketal (1) with TFA followed by trimethylsilyl trifluoromethanesulfonate (TMSOTf) in the presence of a nitrile gives dihydrooxazinones (2) via a new type of modified intramolecular Ritter reaction. The dihydrooxazinones (2) can either be isolated or used directly in reactions with a broad variety of amines. Final deprotection furnishes the 1,1-di-substituted sugar beta-peptides having the general structure (4).
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