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Chemistry Letters
Volumn 37, Issue 5, 2008, Pages 556-557
Synthesis of unnatural mono- and oligosaccharides of farnesol, geraniol, and (S)-Perillyl Alcohol by Biocatalytic Glycosylations
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EID: 45449106872     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.2008.556     Document Type: Article
Times cited : (6)
References (17)
  • 4
    • 0038308362 scopus 로고    scopus 로고
    • S. M. Meadows, D. Mulkerin, J. Berlin, H. Bailey, J. Kolesar, D. Warren, J. P. Thomas, Int. J. Gastrointest. Cancer 2002, 32, 125;
    • S. M. Meadows, D. Mulkerin, J. Berlin, H. Bailey, J. Kolesar, D. Warren, J. P. Thomas, Int. J. Gastrointest. Cancer 2002, 32, 125;
  • 15
    • 45449110094 scopus 로고    scopus 로고
    • Biotransformation of substrates with plant cell cultures was carried out as follows. Prior to this experiment, 100 g of cultured plant cells were individually transplanted to 1-L conical flasks containing 500 mL of Murashige and Skoog's medium (pH 5.7, The cells were grown for an additional 1 month on a rotary shaker (120 rpm) at 25 °C in the dark. Substrate (a total amount of 10 mmol) was administered to ten 1-L conical flasks (1 mmol/flask) containing the suspension cultured cells. After incubation of the cultures for 3 days on a rotary shaker (120 rpm, the cells and medium were separated by filtration with suction. The cells were homogenized (×3) with MeOH. The MeOH-extract was concentrated, and the residue was partitioned between H2O and EtOAc. The H2O layer was applied to a Diaion HP-20 column and the column was washed with H2O followed by elution with MeOH. The MeOH eluate was subjected to HPLC [column: YMC-Pack R&D ODS column 150
    • 2O (3:7, v/v); detection: UV (280 nm); flow rate: 1.0mL/min] to give products.
  • 16
    • 45449109675 scopus 로고    scopus 로고
    • Spectral data for new compounds; product 4: HRFABMS: m/z 407.2411 [M+ Na, 1HNMR (400 MHz, CD3OD, δ; 1.61 (6H, s, H-13, 14, 1.67 (3H, s, H-12, 1.69 (3H, s, H-15, 2.05 (4H, m, H-8, 9, 2.11 (4H, m, H-4, 5, 3.16-3.36 (4H, m, H-2′, 3′, 4′, 5′, 3.67 (1H, dd, J, 12.0, 5.6Hz, H-6a, 3.86 (1H, dd, J= 12.4, 2.4Hz, H-6b, 4.23 (1H, d, J, 8.0Hz, H-1a, 4.28 (1H, d, J, 8.0Hz, H-1′, 4.34 (1H, d, J, 8.0Hz, H-1b, 5.10 (2H, t, J, 7.0Hz, H-6, 10, 5.37 (1H, t, J, 7.0Hz, H-2, 13CNMR (100 MHz, CD3OD, δ 16.5 (C-14, 17.8 (C-15, 25.9 (C-12, 27.4 (C-5, 27.8 (C-9, 40.8 (C-4, 41.0 (C-8, 62.8 (C-6′, 66.3 (C-4′, 71.7 (C-2′, 75.0 (C-5′, 77.9 (C-3′, 102.7 (C-1′, 121.5 (C-2, 125.0 (C-6, C-10, 132.4 (C-7, C-11, 141.7 (C-3, Product 5: HRFABMS: m/z 339.1790 [M, Na, 1HNMR CD3
    • 3OD): δ 20.9 (C-10), 27.5 (C-6), 28.8 (C-5), 31.7 (C-3), 42.5 (C-4), 62.2 (C-6″, C-6‴), 62.7 (C-6′ 71.5 (C-4‴), 73.3 (C-5″), 73.8 (C-2″), 74.2 (C-2‴), 74.5 (C-7), 74.7 (C-3‴, C-5‴), 74.9 (C-2′75.1 (C-3″), 76.5 (C-5′77.8 (C-3′), 81.3 (C-4′, C-4″). 102.6 (C-1‴), 102.8 (C-1′, C-1″), 109.1 (C-9), 125.9 (C-2), 135.4 (C-1), 150.9 (C-8).
  • 17
    • 45449110095 scopus 로고    scopus 로고
    • Glycosylation with CGTase was carried out as follows. To a solution containing 10 mL of 25 mM sodium phosphate buffer (pH 7.0), 0.5 mmol of perillyl β-D-glucoside (6), and 5 g of soluble starch was added 300 units of CGTase from Bacillus macerans. After incubation of the mixture for 24 h at 40°C, the mixture was centrifuged at 3000 g for 10 min. The supernatant was subjected to Sephadex G-25 column chromatography. The glycoside fractions were lyophilized and purified by preparative HPLC to give products.
    • Glycosylation with CGTase was carried out as follows. To a solution containing 10 mL of 25 mM sodium phosphate buffer (pH 7.0), 0.5 mmol of perillyl β-D-glucoside (6), and 5 g of soluble starch was added 300 units of CGTase from Bacillus macerans. After incubation of the mixture for 24 h at 40°C, the mixture was centrifuged at 3000 g for 10 min. The supernatant was subjected to Sephadex G-25 column chromatography. The glycoside fractions were lyophilized and purified by preparative HPLC to give products.

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