High-throughput synthesis and analysis of acylated cyanohydrins

被引:23
作者
Hamberg, Anders
Lundgren, Stina
Wingstrand, Erica
Moberg, Christina [1 ]
Hult, Karl
机构
[1] KTH Sch Chem Sci & Engn, SE-10044 Stockholm, Sweden
[2] AlbaNova Univ Ctr, Dept Biochem, Sch Biotechnol, SE-10691 Stockholm, Sweden
关键词
asymmetric synthesis; cyanohydrins; enantioselectivity; enzymes; high-throughput screening; microreactors;
D O I
10.1002/chem.200601638
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The yields and optical purities of products obtained from chiral Lewis acid/Lewis base-catalysed additions of alpha-ketonitriles to prochiral aldehydes could be accurately determined by an enzymatic method. The amount of remaining aldehyde was determined after its reduction to an alcohol, whilst the two product enantiomers were analysed after subsequent hydrolysis first by the (S)-selective Candida antarctica lipase B and then by the unselective pig liver esterase. The method could be used for analysis of products obtained from a number of aromatic aldehydes and aliphatic ketonitriles. Microreactor technology was successfully combined with high-throughput analysis for efficient catalyst optimization.
引用
收藏
页码:4334 / 4341
页数:8
相关论文
共 75 条
[1]   EMDee: An enzymatic method for determining enantiomeric excess [J].
Abato, P ;
Seto, CT .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (37) :9206-9207
[2]  
[Anonymous], 1997, ANGEW CHEM
[3]  
[Anonymous], ANGEW CHEM
[4]  
[Anonymous], ANGEW CHEM
[5]  
[Anonymous], ANGEW CHEM
[6]   Enantioselective catalysis and analysis on a chip [J].
Belder, D ;
Ludwig, M ;
Wang, LW ;
Reetz, MT .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (15) :2463-2466
[7]   The fabrication of micro-porous silica structures for micro-reactor technology [J].
Christensen, PD ;
Johnson, SWP ;
McCreedy, T ;
Skelton, V ;
Wilson, NG .
ANALYTICAL COMMUNICATIONS, 1998, 35 (10) :341-343
[8]   A chemosensor-based approach to catalyst discovery in solution and on solid support [J].
Copeland, GT ;
Miller, SJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (17) :4306-4307
[9]   Fast parallel enantiomeric analysis of unmodified amino acids by sensing with fluorescent β-cyclodextrins [J].
Corradini, R ;
Paganuzzi, C ;
Marchelli, R ;
Pagliari, S ;
Sforza, S ;
Dossena, A ;
Galaverna, G ;
Duchateau, A .
JOURNAL OF MATERIALS CHEMISTRY, 2005, 15 (27-28) :2741-2746
[10]  
Dahmen S, 2001, SYNTHESIS-STUTTGART, P1431