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Seven differently glycosidated sugar amino acids (SSAs) derived from glucosamine have been prepared. Following standard solution-phase peptide-coupling procedures, the glycosidated 2-amino-2-deoxy-D- glucopyranosiduronic acids were condensed with natural amino acids to furnish useful heterodi- and -trimeric building blocks to be used in peptide synthesis. Combinations of these building blocks yielded hetero-oligomeric peptides with two sugar amino acid units in different distances to each other. These were prepared to evaluate the influence of glycosidic side chains on the peptide backbone. Conformations of selected examples were examined by means of ROESY spectroscopy in combination with molecular dynamics (MD) simulations and circular-dichroism (CD) studies.
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Reference：
Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics