The ability of GH 39 beta-D-Xylosidase (XylBH39) from Bacillus halodurans to catalyze transxylosylation reactions, particularly for the production of alkyl xylosides, has been investigated using p-nitrophenyl (pNP) beta-D-xylopyranoside, xylobiose and xylotriose. Furthermore wheat bran, being rich in xylo-oligosaccharides after enzymatic treatment with an endoxylanase. was used as a source of xylosyl donors. The autocondensation of pNP beta-D-Xylopyranoside was characterized by poor regioselectivity and the production of a variety of short (di- and trimers) oligosaccharides. Compared to xylobiose, xylotriose was a better donor molecule for XylBH39-mediated transxylosylation of primary alcohols presenting chain length from 1- to 5-carbon atoms. Using a wheat bran hydrolysate, generated using an endoxylanase, it was possible to perform XylBH39-mediated transxylosylation of propan-1-ol to produce propyl beta-D-xylopyranoside. This enzymatic process led to synthesis of 0.9 g of propyl beta-D-Xylopyranoside from 20 g of destarched wheat bran.