Convenient synthesis of alkyl and phenylalkyl β-d-glucopyranosides using facile and novel biocatalysts of plant origin

Abstract

Several kinds of fruit and vegetable seed meals were examined as the novel biocatalysts for the synthesis of alkyl and phenylalkyl glycosides, an important group of nonionic surfactants, from d-glucose and primary alcohols. The crude enzymes from prune and black plum seeds displayed comparable or slightly higher catalytic efficiency and better operational stability as compared to those from apple and peach seeds. These alkyl glycosides were synthesized with the yields of 14–78% using prune seed meals. In addition, synthetic yields of alkyl and phenylalkyl glycosides decreased dramatically with the elongation of the chain of the primary alcohols. In the synthesis of octyl β-d-glucopyranoside, the maximal yield of 14% was obtained with prune seed meals. However, in the synthesis of ethyl, propyl and butyl β-d-glucopyranoside with the same catalyst, the yields were 78%, 69% and 53%, respectively, which were much higher than that of octyl β-d-glucopyranoside. Enzymatic synthesis of butyl β-d-glucopyranoside was conducted on a 0.9g scale, with an average isolated yield of 30% for the first two batches.