Enantioselective glucosylation of (R,S)-1-phenylethanol by the cultured suspension cells of higher plants

Chemistry Letters

Volumn , Issue 8, 1996, Pages 719-720

  Lee, Ym Sook ^b   Ito, Diana I ^a   Koya, Kazuhiko ^a   Izumi, Shunsuke ^a   Hirata, Toshifumi ^a  

^a HIROSHIMA UNIVERSITY   (Japan)

^b Kyungnam University   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0030495848     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.1996.719     Document Type: Article

References (22)

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10. 12 supplemented with 3% sucrose and 10 mM 2,4-dichlorophenoxy acetic acid (2,4-D). Green cells were obtained by culturing the white cells under illumination (4000 lux) in MS medium with 1% sucrose and 5 mM 2,4-D. The flasks were shaken on a rotary shaker (75 rpm) at 25°C.
11. T. Hirata, T. Aoki, Y. Hirano, T. Ito, and T. Suga, Bull. Chem. Soc. Jpn., 54, 3527 (1981).
12. T. Murashige and F. Skoog, Physiol. Plant., 15, 473 (1962).
13. 15 supplemented with 3% of sucrose and 10 mM 2,4-D under illumination (4000 lux). The flasks were shaken on a rotary shaker (75 rpm) at 25°C.
14. H. Hamada, Y. Fuchikami, Y. Ikematsu, T. Hirata, H. Williams, and A. I. Scott, Phytochemistry, 37, 1037 (1994).
15. R. U. Schenk and A. C. Hildebrand, Can. J. Botany, 50, 199 (1972).
16. 2O and EtOAc. The aqueous layer was further extracted with BuOH. The filtered medium was extracted with EtOAc and then with BuOH. The BuOH extracts from both cells and culture medium gave compound 3 by column chromatography on silica gel.
17. Y. Ooi, N. Mitsuo, and T. Satoh, Chem. Pharm. Bull., 33, 5547 (1985).
18. 3) δ 78.1 (C-1), 24.3 (C-2), 143.3 (C-3), 128.2 (C-4, 8), 126.7 (C-5, 7), 127.6 (C-6), 101.5 (C-1′), 73.4 (C-2′), 76.4 (C-3′), 69.5 (C-4′), 75.5 (C-5′), 61.5 (C-6′).
19. 3): δ 75.6 (C-1), 22.2 (C-2), 142.0 (C-3), 128.6 (C-4, 8), 126.5 (C-5, 7), 127.8 (C-6), 99.7 (C-1′), 73.3 (C-2′), 76.2 (C-3′), 69.3 (C-4′), 75.3 (C-5′), 61.2 (C-6′).
20. Glucoside 3 was incubated for 22 h at 37°C with 93U β-glucosidase from sweet almond and 0.8 ml phosphate buffer (0.1 M, pH 6.0). The mixture was extracted with ether and the crude product was purified by TLC to give 1-phenylethanol.
21. 1H NMR of 3 were used for the determination of the diastereomeric excess. The enantiomeric compositions of the aglycone moieties were confirmed by analysis of the hydrolyzed alcohol with GLC on CP-cyclodextrin-β-236-M19 column.
22. T. Suga, T. Hirata, and S. Izumi, Phytochemistry, 25, 2791 (1986).