150995-11-2Relevant articles and documents
Preparation of Tea Aroma Precursor Glycosides: An Efficient and Sustainable Approach via Chemical Glycosidation
Li, Tianlu,Li, Tong,Zhang, Youqin,Schmidt, Richard R.,Peng, Peng
, p. 2320 - 2327 (2022/02/23)
Tea aroma precursor glycosides are plant-derived natural products with great economic value. However, the preparation of these glycosides remains largely overlooked in the past decades. Herein, we report a mild, efficient, and sustainable chemocatalytic procedure for the production of tea aroma precursor glycosides. During the study of the glycosidation, the catalysts were found to be decisive in the product formation favoring different reaction pathways; in addition, the influence of molecular sieves was elucidated. With regard to these findings, the serious problem of the competing orthoester formation side reaction was successfully overcome with low catalyst loading (1 mol %) and the use of 5 ? molecular sieves, leading to the preparation of a variety of tea aroma precursor β-d-glucopyranosides and β-primeverosides on a gram scale in high yields in an economical way. Taken together, the current approach features catalytic glycosidation with non-toxic and low-cost catalysts, demonstrates highly favorable greenness and sustainability, and promises industrial production of tea aroma precursor glycosides.
Efficient synthesis of β-primeverosides as aroma precursors by transglycosylation of β-diglycosidase from Penicillium multicolor
Tsuruhami, Kazutaka,Mori, Shigeharu,Sakata, Kanzo,Amarume, Satoshi,Saruwatari, Shigetaka,Murata, Takeomi,Usui, Taichi
, p. 849 - 863 (2007/10/03)
The enzyme activity transferring a β-primeverosyl unit was found from culture filtrates of Penicillium multicolor IAM7153 and was useful for synthesizing a series of β-primeverosides via a β-primeverosyl transfer reaction in an aqueous-organic biphasic system. With the acceptors benzyl alcohol, 2-phenylethanol, and (Z)-3-hexenol, the enzyme induced the transfer products benzyl, 2-phenylethyl, and (Z)-3-hexyl β-primeverosides in high yields of 51% to 70% based on the donor added. When geraniol and eugenol were used as acceptors, the corresponding geranyl and eugenyl β-primeverosides were obtained in lower yields of 8% to 12%. The enzyme was an excellent tool for producing naturally occurring β-primeverosides on a mmol scale. Copyright Taylor & Francis LLC.
