Highly enantioselective DNA-based catalysis

被引:159
作者
Roelfes, G [1 ]
Boersma, AJ [1 ]
Feringa, BL [1 ]
机构
[1] Univ Groningen, Stratingh Inst, Dept Organ Chem, Groningen, Netherlands
关键词
D O I
10.1039/b516552k
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A new approach to DNA-based asymmetric catalysis is presented, which gives rise to very high enantioselectivities (up to 99% ee) in the copper catalyzed Diets-Alder reaction in water.
引用
收藏
页码:635 / 637
页数:3
相关论文
共 25 条
[1]   CRYSTAL STRUCTURE OF IODIBOS-(2,2'-BIPYRIDYL)COPPER(II) IODIDE [J].
BARCLAY, GA ;
KENNARD, CHL ;
HOSKINS, BF .
JOURNAL OF THE CHEMICAL SOCIETY, 1963, (DEC) :5691-&
[2]   STRUCTURAL RESEARCH ON MIXED THIOCYANATE COPPER(II) COMPLEXES WITH MULTIDENTATE LIGANDS CONTAINING NITROGEN AS DONOR ATOM - CRYSTAL AND MOLECULAR-STRUCTURES OF ISOTHIOCYANATO[NN'-BIS(2-PYRIDYLMETHYLENE)TETRAMETHYLENEDIAMINE]COPPER(II) THIOCYANATE AND OF BIS(ISOTHIOCYANATO)[2-(2-PYRIDYL)BENZIMIDAZOLE]COPPER(II)C [J].
BATTAGLIA, LP ;
BELICCHIFERRARI, M ;
BONAMARTINICORRADI, A ;
GASPARRIFAVA, G ;
PELIZZI, C ;
VIDONITANI, ME .
JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS, 1976, (21) :2197-2202
[3]   Recognition and reaction of metallointercalators with DNA [J].
Erkkila, KE ;
Odom, DT ;
Barton, JK .
CHEMICAL REVIEWS, 1999, 99 (09) :2777-2795
[4]   A ribozyme for the aldol reaction [J].
Fusz, S ;
Eisenführ, A ;
Srivatsan, SG ;
Heckel, A ;
Famulok, M .
CHEMISTRY & BIOLOGY, 2005, 12 (08) :941-950
[5]   Directed evolution of nucleic acid enzymes [J].
Joyce, GF .
ANNUAL REVIEW OF BIOCHEMISTRY, 2004, 73 :791-836
[6]  
Lu Y, 2002, CHEM-EUR J, V8, P4589
[7]   Effects of Lewis acid-surfactant-combined catalysts on aldol and Diels-Alder reactions in water [J].
Manabe, K ;
Mori, Y ;
Kobayashi, S .
TETRAHEDRON, 1999, 55 (37) :11203-11208
[8]   Covalent Schiff base catalysis and turnover by a DNAzyme:: A M2+ independent AP-endonuclease mimic [J].
May, JP ;
Ting, R ;
Lermer, L ;
Thomas, JM ;
Roupioz, Y ;
Perrin, DM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (13) :4145-4156
[9]   Design of copper DNA intercalators with leishmanicidal activity [J].
Navarro, M ;
Cisneros-Fajardo, EJ ;
Sierralta, A ;
Fernández-Mestre, M ;
Silva, P ;
Arrieche, D ;
Marchán, E .
JOURNAL OF BIOLOGICAL INORGANIC CHEMISTRY, 2003, 8 (04) :401-408
[10]   A systematic study of ligand effects on a Lewis-acid-catalyzed Diels-Alder reaction in water. Water-enhanced enantioselectivity [J].
Otto, S ;
Engberts, JBFN .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (29) :6798-6806