pH-dependent mutarotation of 1-thioaldoses in water. Unexpected behavior of (2s)-D-aldopyranoses.
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.
Caraballo
Rémi
R
KTH-Royal Institute of Technology, Department of Chemistry, Teknikringen 30, S-10044 Stockholm, Sweden.
Deng
Lingquan
L
Amorim
Luis
L
Brinck
Tore
T
Ramström
Olof
O
D002236:Carbohydrate Conformation; D005690:Galactose / Q000031:analogs & derivatives* / Q000737:chemistry*; D006863:Hydrogen-Ion Concentration; D012399:Rotation; D014867:Water / Q000737:chemistry*
D014867:Water; D005690:Galactose