Synthesis and conformational analysis of neoglycoconjugates derived from O- and S-glucose

• Published in: Carbohydrate research Vol. 373; pp. 1 - 8
• Main Authors: Rojas, Víctor, Carreras, Javier, Corzana, Francisco, Avenoza, Alberto, Busto, Jesús H., Peregrina, Jesús M.
• Format: Journal Article
• Language: English
• Published: OXFORD Elsevier Ltd 24.05.2013; Elsevier
• Subjects: Biochemistry & Molecular Biology; Carbohydrate Conformation; Carbohydrates; Chemistry; Chemistry Techniques, Synthetic; Chemistry, Applied; Chemistry, Organic; Conformation analysis; Cross-coupling; Cysteine - chemistry; Glucose - chemistry; Glycoconjugates; Glycoconjugates - chemical synthesis; Glycoconjugates - chemistry; Life Sciences & Biomedicine; Magnetic Resonance Spectroscopy; Molecular Dynamics Simulation; NMR spectroscopy; Physical Sciences; Science & Technology; Serine - chemistry; Conformation analysis; Carbohydrates; Cross-coupling; Glycoconjugates; NMR spectroscopy; SER; OLIGOSACCHARIDES; MOLECULAR-MECHANICS; LINKED GLYCOPEPTIDES; NMR; THIOOLIGOSACCHARIDES; DYNAMICS; BINDING; GLYCOSYL AMINO-ACIDS; GLYCOBIOLOGY
• ISSN: 0008-6215; 1873-426X
• DOI: 10.1016/j.carres.2013.02.013

[Display omitted] • The synthesis and the conformational analysis of four novel neoglycopeptides derived from glucose are described. • These neoglycopeptides incorporate both S- and O-glycosidic linkages. • The sugar and peptide moieties are linked by a four-atom carbon spacer. • The linker allows the carbohydrate to explore a wide-ranging conformational space. Using olefin metathesis as a key step, four neoglycoconjugates incorporating α-O-glucose, α-S-glucose or β-S-glucose as a carbohydrate unit and l-serine or l-cysteine as an amino acid moiety have been synthesized. The four-atom carbon spacer allows the carbohydrate to explore a wide-ranging conformational space, which may have important implications for the molecular recognition of these molecules.