34047-83-1Relevant academic research and scientific papers
A novel strategy to improve the aromatic alcohols tolerance of enzyme for preparative-scale synthesis of natural glycosides
Zhou, Youzhi,Zhao, Lu,Liu, Ke,Zhang, Jinsong,Chu, Jianlin,He, Bingfang
, p. 9 - 12 (2017/08/22)
Aromatic alcohols are liable to result in enzyme inactivation. A novel strategy was established for improving the aromatic alcohol tolerance of β-galactosidase (BMG) from Bacillus megaterium YZ08. The half-life of BMG in 200 mM vanillyl alcohol solution was dramatically increased by 9–123 times with the addition of hydrophilic solvents. In 30% DMSO, the reaction concentration of aromatic alcohol could reach up to 300–400 mM, and 0.85–2.44 g of natural glycosides were successfully obtained in 100 mL-scale. The simple and effective strategy shows potential applications when dealing with the preparative-scale exploitation of enzymatic reactions.
Alkenyl β-d-galactopyranoside derivatives as efficient chiral templates in stereoselective cyclopropanation and epoxidation reactions
Vega-Perez, Jose M.,Perinan, Ignacio,Palo-Nieto, Carlos,Vega-Holm, Margarita,Iglesias-Guerra, Fernando
experimental part, p. 81 - 95 (2010/04/06)
The synthesis of a wide range of alkenyl 4,6-O-(S)-benzylidene-β-d-galactopyranosides is described. The cyclopropanation and epoxidation reactions of these compounds were developed. Cyclopropanation reactions took place with high stereoselectivity giving diastereomeric excesses of up to 100%. As a part of our aim in studying hydroxyl-directed reactions, their epoxidation with m-CPBA was carried out. High diastereomeric excesses (80-100%) were obtained when the hydroxyl group at C-2 of the auxiliary was unprotected. The β-d-galactopyranoside moiety constitutes as an interesting auxiliary, due to its efficient chirality transfer capability as well as providing a way to obtain a variety of glycolipid derivatives.
GLYCOSIDES OF CINNAMYL ALCOHOL FROM THE RHIZOMES OF Rhodiola rosea
Zapesochnaya, G. G.,Kurkin, V. A.
, p. 685 - 688 (2007/10/02)
Three new cinnamyl alcohol glycosides have been isolated for the first time from the rhizomes of roseroot stonecrop Rhodiola rosea L. (Sedum rosea).On the basis of chemical transformations and the results of UV, IR, PMR, and mass spectroscopy the following structures are proposed for the compounds isolated: rozin - trans-cinnamyl O-β-D-glucopyranoside; rozavin - trans-cinnamyl O-(6'-O-α-L-arabinopyranosyl-β-D-glucopyranoside); and rozarin - trans-cinnamyl O-(6'-O-α-L-arabinofuranosyl-β-D-glucopyranoside).
