title: pH-dependent mutarotation of 1-thioaldoses in water. Unexpected behavior of (2s)-D-aldopyranoses.
abstract: The pH-dependent mutarotation of 1-thioaldopyranoses in aqueous media has been investigated. Anomerization readily occurred at lower and neutral pH for all aldopyranoses studied, whereas mainly for (2S)-D-aldopyranoses at higher pH. 1-Thio-D-mannopyranose and 1-thio-D-altropyranose showed very strong pH dependence where the anomeric equilibrium ratios changed dramatically from a preference for the β-anomer at lower pH to the α-anomer at higher pH.
authors.affiliation: KTH-Royal Institute of Technology, Department of Chemistry, Teknikringen 30, S-10044 Stockholm, Sweden.
authors.forename: Rémi
authors.initials: R
authors.lastname: Caraballo
authors.forename: Lingquan
authors.initials: L
authors.lastname: Deng
authors.forename: Luis
authors.initials: L
authors.lastname: Amorim
authors.forename: Tore
authors.initials: T
authors.lastname: Brinck
authors.forename: Olof
authors.initials: O
authors.lastname: Ramström
mesh_terms: D002236:Carbohydrate Conformation; D005690:Galactose / Q000031:analogs & derivatives* / Q000737:chemistry*; D006863:Hydrogen-Ion Concentration; D012399:Rotation; D014867:Water / Q000737:chemistry*
chemical_list: D014867:Water; D005690:Galactose