- Preparation of Tea Aroma Precursor Glycosides: An Efficient and Sustainable Approach via Chemical Glycosidation
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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.
- Li, Tianlu,Li, Tong,Zhang, Youqin,Schmidt, Richard R.,Peng, Peng
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p. 2320 - 2327
(2022/02/23)
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- Tea leaf perfumery precursor glucoside and synthesizing method thereof
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The invention relates to a tea leaf perfumery precursor glucoside and a synthesizing method thereof. The synthesizing method comprises the following steps of synthesizing ten glucosides including aromatic alcohol ( alkanol )-beta -D-glucosides and aromatic alcohol (alkanol )-beta -D-primrose indicans. The synthesizing method disclosed by the invention is a glucoside synthesizing method which is good in selectivity, high in production rate and low in cost.
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Paragraph 0109-0111; 0116-0117
(2020/07/02)
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- Chemoenzymatic synthesis of naturally occurring (Z)-3-hexenyl 6-O-glycosyl-β-d-glucopyranosides
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Direct β-glucosidation between cis-3-hexen-1-ol and d-glucose (5) using the immobilized β-glucosidase from almonds with the synthetic prepolymer ENTP-4000 gave (Z)-3-hexenyl β-d-glucoside (1) in 17% yield. The coupling of the (Z-3-hexenyl O-β-d-glucopyran
- Kishida, Masashi,Fujii, Mikio,Ida, Yoshiteru,Akita, Hiroyuki
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p. 2127 - 2137
(2007/10/03)
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- Efficient synthesis of β-primeverosides as aroma precursors by transglycosylation of β-diglycosidase from Penicillium multicolor
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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.
- Tsuruhami, Kazutaka,Mori, Shigeharu,Sakata, Kanzo,Amarume, Satoshi,Saruwatari, Shigetaka,Murata, Takeomi,Usui, Taichi
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p. 849 - 863
(2007/10/03)
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