Enantioselective glucosylation of (±)-secondary alcohols with plant glucosyltransferases

Tetrahedron Asymmetry

Volumn 15, Issue 15, 2004, Pages 2319-2321

  Shimoda, Kei ^a   Kubota, Naoji ^a   Hamada, Hiroki ^b  

^a OITA UNIVERSITY   (Japan)

^b OKAYAMA UNIVERSITY OF SCIENCE   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DERIVATIVE; GLUCOSIDE; GLUCOSYLTRANSFERASE;

ARTICLE; CATHARANTHUS ROSEUS; ENANTIOSELECTIVITY; ENZYME SYNTHESIS; GLYCOSYLATION; NONHUMAN; PLANT CELL CULTURE; PRIORITY JOURNAL; PROTEIN EXPRESSION; TOBACCO;

EID: 4143149941     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetasy.2004.06.022     Document Type: Article

References (24)

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13. 5 by the same procedure: GTF-II, monomeric form with molecular mass of ca. 51 kDa
14. 7 Each suspension cells were incubated on a rotary shaker (75 rpm) at 25°C for 3 weeks prior to use for enzyme preparation
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20. 12,13
21. Product glucosides were incubated with almond-β-glucosidase (90 U) and 1 mL of phosphate buffer (0.1 M, pH 6.0) at 37 A°C for 24 h. After 24 h incubation, the glucosides were completely hydrolyzed to the alcohols as judged by HPLC and TLC analyses of the reaction mixture. The reaction mixture was extracted with diethyl ether to give a crude alcohol fraction, which was purified by column chromatography on silica gel with pentane-ethyl acetate (9:1, v/v) to yield the hydrolyzed alcohols
22. -1). Retention times for alcohols 1-5 in the GLC were as follows: (S)- and (R)-1, 9.7 and 10.2 min; (S)- and (R)-2, 12.6 and 13.2 min; (R)- and (S)-3, 15.1 and 16.5 min; (1S,2R,5S)- and (1R,2S,5R)-4, 20.0 and 20.3 min; (1S,2S)- and (1R,2R)-5, 27.7 and 28.9 min
23. 2 [ α ] D 20 = - 22 }. The optical rotation data of the products 6-9 could not be obtained due to the low transformation rate and lack of products
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