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 stron...

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Veröffentlicht in:	Journal of organic chemistry 2010-09, Vol.75 (18), p.6115-6121
Hauptverfasser:	Caraballo, Rémi, Deng, Lingquan, Amorim, Luis, Brinck, Tore, Ramström, Olof
Format:	Artikel
Sprache:	eng
Schlagworte:	Anomeric equilibrium Anomerization Aqueous media Carbohydrate Conformation Carbohydrates with 4, 5, 6, ... C atoms, dissacharides and oligosaccharides Carbohydrates. Nucleosides and nucleotides Chemistry Exact sciences and technology Galactose - analogs & derivatives Galactose - chemistry Hydrogen-Ion Concentration Kemi Mannopyranose Mutarotation NATURAL SCIENCES NATURVETENSKAP Neutral pH Organic chemistry PH dependence PH-dependent Preparations and properties Rotation Water - chemistry
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Zusammenfassung:	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.
ISSN:	0022-3263 1520-6904 1520-6904
DOI:	10.1021/jo100826e