Cellular uptake and saccharide chain elongation of "fluoro-amphiphilic" glycosides

被引:15
作者
Kasuya, MCZ
Ito, A
Cusi, R
Sato, T
Hatanaka, K
机构
[1] Univ Tokyo, Inst Ind Sci, Meguro Ku, Tokyo 1538505, Japan
[2] Keio Univ, Grad Sch Sci & Engn, Kouhoku Ku, Yokohama, Kanagawa 2238522, Japan
关键词
D O I
10.1246/cl.2005.856
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Fluoro-amphiphilic glycosides are practical alternatives for the preparation of oligosaccharides. Fluoro-amphiphilic saccharide primers possessing a hydrophilic sugar moiety and a fluorous tag could be taken up by cells and elongated by cellular enzymes. The elongated products were released by cells to the culture medium and could be easily separated from other components by simple extraction with a fluorous solvent.
引用
收藏
页码:856 / 857
页数:2
相关论文
共 13 条
[1]   Fluorous synthesis with fewer fluorines (light fluorous synthesis): separation of tagged from untagged products by solid-phase extraction with fluorous reverse-phase silica gel [J].
Curran, DP ;
Luo, ZY .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (39) :9069-9072
[2]   Tris(2-(perfluorohexyl)ethyl)tin hydride: A new fluorous reagent for use in traditional organic synthesis and liquid phase combinatorial synthesis [J].
Curran, DP ;
Hadida, S .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (10) :2531-2532
[3]   Fluorous phase chemistry: a new industrial technology [J].
Dobbs, AP ;
Kimberley, MR .
JOURNAL OF FLUORINE CHEMISTRY, 2002, 118 (1-2) :3-17
[4]   Introduction - Fluorous chemistry: from biphasic catalysis to a parallel chemical universe and beyond [J].
Gladysz, JA ;
Curran, DP .
TETRAHEDRON, 2002, 58 (20) :3823-3825
[5]   Fluorous-tagged compound: a viable scaffold to prime oligosaccharide synthesis by cellular enzymes [J].
Kasuya, MCZ ;
Cusi, R ;
Ishihara, O ;
Miyagawa, A ;
Hashimoto, K ;
Sato, T ;
Hatanaka, K .
BIOCHEMICAL AND BIOPHYSICAL RESEARCH COMMUNICATIONS, 2004, 316 (03) :599-604
[6]   Azido glycoside primer: a versatile building block for the biocombinatorial synthesis of glycosphingolipid analogues [J].
Kasuya, MCZ ;
Wang, LX ;
Lee, YC ;
Mitsuki, M ;
Nakajima, H ;
Miura, Y ;
Sato, T ;
Hatanaka, K ;
Yamagata, S ;
Yamagata, T .
CARBOHYDRATE RESEARCH, 2000, 329 (04) :755-763
[7]   Fluorous mixture synthesis: A fluorous-tagging strategy for the synthesis and separation of mixtures of organic compounds [J].
Luo, ZY ;
Zhang, QS ;
Oderaotoshi, Y ;
Curran, DP .
SCIENCE, 2001, 291 (5509) :1766-1769
[8]   A new fluorous/organic amphiphilic ether solvent, F-626: execution of fluorous and high temperature classical reactions with convenient biphase workup to separate product from high boiling solvent [J].
Matsubara, H ;
Yasuda, S ;
Sugiyama, H ;
Ryu, I ;
Fujii, Y ;
Kita, K .
TETRAHEDRON, 2002, 58 (20) :4071-4076
[9]   Glycosylation of lactosylceramide analogs in animal cells: Amphipathic disaccharide primers for glycosphingolipid synthesis [J].
Miura, Y ;
Yamagata, T .
BIOCHEMICAL AND BIOPHYSICAL RESEARCH COMMUNICATIONS, 1997, 241 (03) :698-703
[10]   Glycosylation of amphipathic lactoside primers with consequent inhibition of endogenous glycosphingolipid synthesis [J].
Nakajima, H ;
Miura, Y ;
Yamagata, T .
JOURNAL OF BIOCHEMISTRY, 1998, 124 (01) :148-156