The identification of 1,3-oxazolidine-2-thiones and 1,3-thiazolidine-2-thiones from the reaction of glucose with benzyl isothiocyanate.
The structure of interaction products resulting from the reaction of unmodified glucose with benzyl isothiocyanate is reported. Prior to their identification, the main products of this reaction were isolated using solid-phase extraction (SPE) as well as preparative HPLC. They were then identified by NMR and MS as 3-benzyl-4-hydroxy-5-(D-arabino-1,2,3,4-tetrahydroxybutyl)-1,3-oxazolidine-2-thione, 3-benzyl-4-hydroxy-4-hydroxymethyl-5-(D-erythro-1,2,3-trihydroxypropyl)-1,3-oxazolidine-2-thione, N-benzyl-(D-gluco-4,5-dihydroxy-6-hydroxymethyl-tetrahydropyrano)[2,3-b]oxazolidine-2-thione and 3-benzyl-4-(N-benzyl amino)-5-(D-arabino-1,2,3,4-tetrahydroxybutyl)-1,3-thiazolidine-2-thione. The identity of the last compound was secured by X-ray crystal structure data.
Kruse
Hans-P
HP
University of Potsdam, Institute of Nutritional Science, Arthur-Scheunert-Allee 114-116, D-14558 Nuthetal, Germany. hpkruse@rz.uni-potsdam.de
Heydenreich
Matthias
M
Engst
Wolfram
W
Schilde
Uwe
U
Kroll
Juergen
J
D002851:Chromatography, High Pressure Liquid; D018360:Crystallography, X-Ray; D005947:Glucose / Q000737:chemistry*; D017879:Isothiocyanates / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D015394:Molecular Structure; D013871:Thiones / Q000032:analysis* / Q000138:chemical synthesis / Q000737:chemistry* / Q000302:isolation & purification
D017879:Isothiocyanates; D013871:Thiones; C031403:benzyl isothiocyanate; D005947:Glucose