2032
S.-X. Song et al. / Bioorg. Med. Chem. Lett. 22 (2012) 2030–2032
Z.; Gao, L.-X.; Shi, X.-X.; Tang, Y.; Xie, J.; Li, J.; Chen, G.-R.; Chen, K.
Acknowledgments
Glycoconjugate J. 2011, 28, 493.
11. Toshima, K.; Tatsuta, K. Chem. Rev. 1993, 93, 1503.
12. Cinget, F.; Schmidt, R. R. Synlett 1993, 168.
13. Kasuya, M. C. Z.; Ikeda, M.; Hashimoto, K.; Sato, T.; Hatanaka, K. J. Carbohydr.
Chem. 2005, 24, 705.
14. Plettenburg, O.; Mui, C.; Bodmer-Narkevitch, V.; Wong, C.-H. Adv. Synth. Catal.
2002, 344, 622.
Project supported by National Natural Science Foundation of
China (Grant No. 21176076, No. 30801405), National Basic
Research Program of China (No. 2007CB914201), Shanghai Science
and Technology Community (No. 10410702700), Chinese Academy
of Sciences (No. KSCX2-EW-R-15) and China Postdoctoral Science
Foundation (2011M500069).
15. Zhang, X.; Kamiya, T.; Otsubo, N.; Ishida, H.; Kiso, M. J. Carbohydr. Chem. 1999,
18, 225.
16. General procedure for the glycosylation: To
a soln. of peracetyl-b-D-O-
galactopyranoside (1 equiv) and the fatty alcohol (2 equiv) in dry MeCN
(10 mL), was added BF3ꢀEt2O (1 equiv). This mixture was transferred to the
microwave oven with rigorous stirring for 12 min at 120 °C (ramp time:
10 min). Solvent was removed in vacuum, and the resulting residue was
diluted with EtOAC and washed successively with sat. NaHCO3 and brine. The
combined organic layer was dried over NaSO4, filtered, concentrated in vacuum
Supplementary data
Supplementary data associated with this article can be found, in
to give
a crude mixture residue which was separated by column
chromatography.
17. General procedure for the deacetylation: To a soln. of peracetyl galactolipid
(1 equiv) in 6 mL MeOH, was added NH3ꢀH2O (3 equiv) and the mixture was
stirred at reflux for 3 h. After removal of the solvent in vacuum, the resulting
References and notes
1. (a) Wu, D.; Fujio, M.; Wong, C.-H. Bioorg. Med. Chem. 2008, 16, 1073; (b) Ricci, J.;
Park, J.; Chung, W.-Y.; Park, K.-K.; Jung, M. Bioorg. Med. Chem. Lett. 2010, 20,
6858; (c) Chen, W.; Xia, C.; Cai, L.; Wang, P. G. Bioorg. Med. Chem. Lett. 2010, 20,
3859.
2. Kuriyama, I.; Musumi, K.; Yonezawa, Y.; Takemura, M.; Maeda, N.; Iijima, H.;
Hada, T.; Yoshida, H.; Mizushina, Y. J. Nutr. Biochem. 2005, 16, 594.
3. Meada, N.; Kokai, Y.; Ohtani, S.; Sahara, H.; Kumamoto-Yonezawa, Y.;
Kuriyama, I.; Hada, T.; Sato; Noriyuki; Yoshida, H.; Mizushina, Y. Lipids 2008,
43, 741.
residue was directly purified by column chromatography. n-Hexacanyl a-D-
galactopyranoside (22a): From compound 15a (649 mg, 1.1 mmol), column
chromatography (CH2Cl2/MeOH = 6:1) afforded compound 22a quantitatively
as a white solid. Rf = 0.60 (CH2Cl2/MeOH = 6:1). ½a D25
ꢁ
= +99.2 (c = 0.1, MeOH).
1H NMR (400 MHz, CDCl3): d = 4.91 (s, 1H), 4.06 (s, 1H), 3.92 (d, J = 8.0 Hz, 1H),
3.83–3.74 (m, 3H), 3.70 (dd, J = 15.9, 7.0 Hz, 1H), 3.55–3.49 (m, 2H), 1.62–1.55
(m, 2H), 1.24 (br s, 26H), 0.86 (t, J = 6.8 Hz, 3H). 13C NMR (400 MHz, CDCl3):
d = 98.6, 70.6, 69.9, 69.8, 69.2, 68.4, 61.9, 31.8, 29.6, 29.5, 29.4, 29.3, 26.0, 22.5,
14.0. HRESIMS m/z: [M+Na]+ calcd. for C22H44O6: 427.3036; found: 427.3039.
4. (a) Li, R.; Manela, J.; Kong, Y.; Ladisch, S. J. Biol. Chem. 2000, 275, 34213; (b)
Fürstner, A. Eur. J. Org. Chem. 2004, 943.
5. Lule, P.; Pérez Gutierrez, R. M. Pharm. Biol. 2005, 43, 313.
6. Samadder, P.; Bittman, R.; Byun, H.-S.; Arthur, G. Biochem. Cell Biol. 2009, 87,
401.
7. Nagano, T.; Pospíšil, J.; Chollet, G.; Schulthoff, S.; Hickmann, V.; Moulin, E.;
Hermann, J.; Müller, R.; Fürstner, A. Chem. Eur. J. 2009, 15, 9697.
8. Jung, M.; Lee, Y.; Moon, H.-I.; Jung, Y.; Jung, H.; Oh, M. Eur. J. Med. Chem. 2009,
44, 3120.
n-Hexadecanyl a-D-galactopyranoside (22b): From compound 15b (996 mg,
0.8 mmol), column chromatography (CH2Cl2/MeOH = 6:1) afforded compound
22b quantitatively as a white solid. Rf = 0.54 (CH2Cl2/MeOH = 6:1). 1H NMR
(400 MHz, DMSO-d6): d = 4.76 (d, J = 4.3 Hz, 1H), 4.65 (d, J = 5.1 Hz, 1H), 4.53 (t,
J = 5.7 Hz, 1H), 4.31 (d, J = 4.5 Hz, 1H), 4.04 (d, J = 7.3 Hz, 1H), 3.74–3.69 (m,
1H), 3.62 (d, J = 2.8 Hz, 1H), 3.52 (dd, J = 11.6, 5.5 Hz, 1H), 3.46 (dd, J = 10.9,
5.6 Hz, 1H), 3.42–3.38 (m, 1H), 3.32–3.25 (m, 3H), 1.52–1.47 (m, 2H), 1.24 (br s,
26H), 0.85 (t, J = 6.8 Hz, 3H).
18. MTT assay: Cell lines were seeded onto a 96-well plate at a concentration of
9. (a) Song, S.-X.; Zhang, H.-L.; Kim, C.-G.; Sheng, L.; He, X.-P.; Long, Y.-T.; Li, J.;
Chen, G.-R. Tetrahedron 2010, 66, 9974; (b) Zhang, H.-L.; He, X.-P.; Sheng, L.;
Yao, Y.; Zhang, W.; Shi, X.-X.; Li, J.; Chen, G.-R. Mol. Divers. 2011, 15, 889.
10. (a) Yang, J.-W.; He, X.-P.; Li, C.; Gao, L.-X.; Sheng, L.; Xie, J.; Shi, X.-X.; Tang, Y.;
Li, J.; Chen, G.-R. Bioorg. Med. Chem. Lett. 2011, 21, 1092; (b) He, X.-P.; Deng, Q.;
Gao, L.-X.; Li, C.; Zhang, W.; Zhou, Y.-B.; Tang, Y.; Shi, X.-X.; Xie, J.; Li, J.; Chen,
G.-R.; Chen, K. Bioorg. Med. Chem. 2011, 19, 3892; (c) He, X.-P.; Li, C.; Wang, Z.-
2000 cells/well and incubated at 37 °C in 5% CO2 for 24 h.
concentrations of the test compounds were added and the plate was
incubated at 37 °C for 72 h before 40 L MTT (5 mg/mL)/well was added.
After 3 h incubation, the medium was removed and 100 L DMSO was added
to each well. The absorbance was measured on SpectraMax 340 microplate
reader at 550 nm with a reference at 690 nm. The optical density of the result
in MTT assay was directly proportional to the number of viable cells.
A range of
l
l