title: Orthogonally Protected Furanoid Sugar Diamino Acids for Solid-Phase Synthesis of Oligosaccharide Mimetics.
abstract: Sugar diamino acids (SDAs), which differ from the widely used sugar amino acids in the presence of a second amino group connected to the carbohydrate core, share structural features of both amino acids and carbohydrates. They can be used for the preparation of linear and branched amide-linked oligosaccharide mimetics. Such oligomers carry free amino groups, which are positively charged at neutral pH, in a spatially defined way and, thus, represent a potential class of aminoglycoside mimetics. We report here the first examples of orthogonally protected furanoid SDAs and their use in solid-phase synthesis. Starting from d-glucose, we developed a divergent synthetic route to three derivatives of 3,5-diamino-3,5-dideoxy-d-ribofuranose. These building blocks are compatible with solid-phase peptide synthesis following the 9-fluorenylmethoxycarbonyl (Fmoc) strategy, which we demonstrate by the synthesis of an SDA tetramer.
authors.affiliation: †Fachbereich Chemie and Konstanz Research School Chemical Biology (KoRS-CB), Universität Konstanz, 78457 Konstanz, Germany.|‡Department of Chemistry, Sacred Heart College (M. G. University), Kochi 682013, India.
authors.forename: Franklin
authors.initials: F
authors.lastname: John
authors.affiliation: †Fachbereich Chemie and Konstanz Research School Chemical Biology (KoRS-CB), Universität Konstanz, 78457 Konstanz, Germany.
authors.forename: Valentin
authors.initials: V
authors.lastname: Wittmann
mesh_terms: D000606:Amino Sugars / Q000138:chemical synthesis* / Q000737:chemistry; D032701:Biomimetics; D005449:Fluorenes / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D009844:Oligosaccharides / Q000138:chemical synthesis* / Q000737:chemistry; D010455:Peptides / Q000737:chemistry*; D060327:Solid-Phase Synthesis Techniques; D013400:Sugar Acids / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: C000604322:3,5-diamino-3,5-dideoxy-d-ribofuranose; D000606:Amino Sugars; D005449:Fluorenes; D009844:Oligosaccharides; D010455:Peptides; D013400:Sugar Acids; C054007:1-(9-fluorenyl)methyl chloroformate