ISSN print edition: 0366-6352 ISSN electronic edition: 1336-9075 Registr. No.: MK SR 9/7 Published monthly

Mild Pfitzner—Moffat oxidation of the (1→3)-β-D -glucan from Saccharomyces cerevisiae

D. Zeković, M. Radulović, A. Nastasović, M. M. Vrvić, D. Jakovljević, and G. Kogan

Alltech, Inc., North American Bioscience Center, Nicholasville, KY 40356, USA

E-mail: grigorij.kogan@savba.sk

Received: 25 October 2005  Revised: 20 February 2006  Accepted: 27 February 2006

Abstract: The structure of the cell wall glucan isolated from the industrial strain of Saccharomyces cerevisiae was characterized as to be composed of a linear (1→3)-β-D-glucan chain with single β-D-glucopyranosyl residues attached to every ninth backbone unit by (1→6)-glycosidic linkages. Mild oxidation of this β-D-glucan with a dimethyl sulfoxide—acetic anhydride reagent yielded an “oxidized” glucan with aldehyde groups introduced at C-6 and carbonyl oxygens located at C-2 and C-4 of the glucopyranosyl rings. The conversion of the oxidized glucan into the polyoxime was used to study the progress of oxidation and to establish the carbonyl groups distribution in this new reactive polysaccharide derived from baker’s yeast cell wall.

Keywords: saccharides - Saccharomyces cerevisae - Pfitzner—Moffat oxidation - biologically and medicinally active compounds

Full paper is available at www.springerlink.com.

DOI: 10.2478/s11696-006-0043-7

Chemical Papers 60 (3) 243–248 (2006)