Original scientific paper

GC-MS Characterization of Acetylated β-D-glucopyranosides: Transglucosylation of Volatile Alcohols Using Almond β-glucosidase

Igor Jerković ; Department of Organic Chemistry and Natural Products, Faculty of Chemical Technology, University of Split, N. Tesle 10/V, 21 000 Split, Croatia
Josip Mastelić ; Department of Organic Chemistry and Natural Products, Faculty of Chemical Technology, University of Split, N. Tesle 10/V, 21 000 Split, Croatia

Abstract

β-D-Glucopyranosides of pentan-1-ol, (±)-pentan-2-ol, hexan-1-ol, octan-1-ol, benzyl alcohol, 2-phenylethanol, (±)-2-phenyl-propan-1-ol, 3-phenyl-propan-1-ol, geraniol and nerol were synthesized by transglucosylation of the respective alcohols with cellobiose using almond β-glucosidase. The reaction was carried out in acetonitrile with acetate buffer (vol. ratio 9:1), with the yields 14.4–45.0 %. Transglucosylation was not enantioselective. The products were characterized by GC-MS analysis of prepared tetraacetyl glucosides. Fragment ion characteristics of the aglucone moiety are present in all mass spectra, along with the fragments obtained from acetylated glucose. Acetylated glucosides are separable on HP-101 column (even diastereomeric tetraacetyl β-glucosides of enantiomeric alcohols).

Keywords

transglucosylation; β -glucosidase; tetraacetyl glucosides; GC-MS

Hrčak ID:

102954

URI

https://hrcak.srce.hr/102954

Publication date:

25.10.2004.

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