- A Sustainable One-Pot, Two-Enzyme Synthesis of Naturally Occurring Arylalkyl Glucosides
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A sustainable, convenient, scalable, one-pot, two-enzyme method for the glucosylation of arylalkyl alcohols was developed. The reaction scheme is based on a transrutinosylation catalyzed by a rutinosidase from A. niger using the cheap commercially available natural flavonoid rutin as glycosyl donor, followed by selective “trimming” of the rutinoside unit catalyzed by a rhamnosidase from A. terreus. The process was validated with the syntheses of several natural bioactive glucosides, which could be isolated in up to 75 % yield without silica-gel chromatography.
- Bassanini, Ivan,Krejzová, Jana,Panzeri, Walter,Monti, Daniela,K?en, Vladimir,Riva, Sergio
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p. 2040 - 2045
(2017/05/16)
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- Simple preparation of phenylpropenoid β-D-glucopyranoside congeners by Mizoroki-Heck type reaction using organoboron reagents
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Palladium(II)-catalyzed carbon-carbon bond formation between allyl 2,3,4,6-tetra-O-acetyl-β-d-glucopyranoside (3) and arylboronic acid congeners gave the corresponding cinnamyl 2,3,4,6-tetra-O-acetyl- β-d-glucopyranosides (4a-m) in good yield. Among them, coupling products 4a-m were converted to not only the naturally occurring phenylpropenoid β-d-glucopyranoside analogues (1a-e) but also the unnaturally ones (1f-m).
- Kishida, Masashi,Akita, Hiroyuki
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p. 10559 - 10568
(2007/10/03)
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- Simple synthesis of phenylpropenoid β-D-glucopyranoside congeners based on Mizoroki-Heck type reaction of organoboron reagents
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Palladium(II)-catalyzed carbon-carbon bond formation between allyl 2,3,4,6-tetra-O-acetyl-β-d-glucopyranoside (3) and phenylboronic acid congeners gave the phenylpropenoid 2,3,4,6-tetra-O-acetyl-β-d- glucopyranoside (4a-f) in good yield. Among them, compounds 4a-c were converted to the naturally occurring phenylpropenoid β-d-glucopyranoside analogues (1a-c).
- Kishida, Masashi,Akita, Hiroyuki
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p. 4123 - 4125
(2007/10/03)
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- Chemoenzymatic syntheses of naturally occurring β-glucosides
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Enzymatic glycosidation of the various kinds of primary alcohols 5, 7, 9, 11, 13 and 15 and 4-nitrophenyl-β-D-glucopyranoside 4 using β- glucosidase from almonds gave stereoselectively β-D-glucosides 6, 8, 10, 12, 14 and 16 including the naturally occurring β-glucosides in moderate yield. Among them, the β-glucosides 6, 8 and 10 were converted to the cyanoglycosides, rhodiocyanoside A 20a, osmaronin 24a and sutherlandin 29, respectively.
- Akita, Hiroyuki,Kurashima, Katsumi,Nakamura, Takuya,Kato, Keisuke
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p. 2429 - 2439
(2007/10/03)
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- GLYCOSIDES OF CINNAMYL ALCOHOL FROM THE RHIZOMES OF Rhodiola rosea
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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).
- Zapesochnaya, G. G.,Kurkin, V. A.
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p. 685 - 688
(2007/10/02)
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