title: Automated Solution-Phase Synthesis of β-1,4-Mannuronate and β-1,4-Mannan.
abstract: The first automated solution-phase synthesis of β-1,4-mannuronate and β-1,4-mannan oligomers has been accomplished by using a β-directing C-5 carboxylate strategy. By utilizing fluorous-tag assisting purification after repeated reaction cycles, β-1,4-mannuronate was synthesized up to a hexasaccharide with limited loading of a glycosyl donor (up to 3.5 equiv) for each glycosylation cycle due to the homogeneous solution-phase reaction condition. After a global reduction of the uronates, the β-1,4-mannan hexasaccharide was obtained, thereby demonstrating a new approach to β-mannan synthesis.
authors.affiliation: †Department of Chemistry, Iowa State University, Ames, Iowa 50011, United States.
authors.forename: Shu-Lun
authors.initials: SL
authors.lastname: Tang
authors.affiliation: †Department of Chemistry, Iowa State University, Ames, Iowa 50011, United States.|‡Department of Chemistry, Indiana University, Bloomington, Indiana 47405, United States.
authors.forename: Nicola L B
authors.initials: NL
authors.lastname: Pohl
mesh_terms: D001331:Automation; D006603:Hexuronic Acids / Q000138:chemical synthesis* / Q000737:chemistry; D008351:Mannans / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D012996:Solutions
chemical_list: D006603:Hexuronic Acids; D008351:Mannans; D012996:Solutions; C081692:beta-1,4-mannan