151843-05-9Relevant articles and documents
Transglycosylation Forms Novel Glycoside Ethyl α-Maltoside and Ethyl α-Isomaltoside in Sake during the Brewing Process by α-Glucosidase A of Aspergillus oryzae
Kojima, Yusuke,Honda, Chihiro,Kobayashi, Izumi,Katsuta, Ryo,Matsumura, Satomi,Wagatsuma, Izumi,Takehisa, Maya,Shindo, Hitoshi,Hosaka, Masaru,Nukada, Tomoo,Tokuoka, Masafumi
, p. 1419 - 1426 (2020)
Sake, the Japanese rice wine, contains a variety of oligosaccharides and glucosides produced by fungal enzymes during the brewing process. This study investigates the effect of knocking out the Aspergillus oryzae α-glucosidase (agdA) gene on the transglycosylation products in brewed sake. In addition to α-ethyl glucoside and α-glyceryl glucoside, the amount of two compounds that have molecular mass values similar to that of ethyl maltose decreased by agdA gene knockout. Both compounds were synthesized, in vitro, from maltose and ethanol with purified agdA. Nuclear magnetic resonance analysis identified the two compounds as ethyl α-maltoside and ethyl α-isomaltoside, respectively, which are novel compounds in sake as well as in the natural environment. Quantitative analysis of 111 commercially available types of sake showed that these novel compounds were widely present at concentrations of several hundred mg/L, suggesting that both of them are ones of the common glycosides in sake.
Protection-free synthesis of alkyl glycosides under hydrogenolytic conditions
Ishihara, Masaki,Takagi, Yuka,Li, Gefei,Noguchi, Masato,Shoda, Shin-Ichiro
, p. 1235 - 1237 (2013/10/22)
A convenient protection-free synthetic route for the preparation of alkyl glycosides has been developed. The alcoholysis of one-step preparable glycosyl donors, 4,6-dibenzyloxy-1,3,5-triazin-2-yl (DBT) glycosides, under hydrogenolytic conditions gave the corresponding glycosides in good yields without the addition of any acid promoters. The method could be successfully applied to the glycosylation of an acidlabile oligosaccharide.
