The 4-tert-butylphenyl group as a simple tag for solution phase synthesis

被引:3
作者
Blodgett, J
Li, TY
机构
[1] Mississippi State Univ, Dept Chem, Mississippi State, MS 39762 USA
[2] Vanderbilt Univ, Dept Chem, Nashville, TN 37235 USA
关键词
solution phase synthesis; tag synthesis; liquid phase synthesis; cyclodextrin; affinity purification; affinity chromatography;
D O I
10.1016/j.tetlet.2004.07.010
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A solution phase synthesis strategy was investigated using 4-tert-butylphenyl group as the tag and a beta-cyclodextrin column as the affinity chromatographic support for the isolation of compounds containing the tag. It was found that compounds containing the tag have significantly longer retention times on the beta-cyclodextrin column than those compounds that do not have such a tag. The tag is chemically inert and can be introduced onto and removed from target compounds readily. This solution phase synthesis method was applied to the synthesis of some simple amino acid derivatives. (C) 2004 Elsevier Ltd. All rights reserved.
引用
收藏
页码:6649 / 6652
页数:4
相关论文
共 14 条
[1]   SEPARATION OF DRUG STEREOISOMERS BY THE FORMATION OF BETA-CYCLODEXTRIN INCLUSION COMPLEXES [J].
ARMSTRONG, DW ;
WARD, TJ ;
ARMSTRONG, RD ;
BEESLEY, TE .
SCIENCE, 1986, 232 (4754) :1132-1135
[2]   LIQUID-PHASE SYNTHESIS OF PEPTIDES [J].
BAYER, E ;
MUTTER, M .
NATURE, 1972, 237 (5357) :512-&
[3]   ADVANCES IN THE SYNTHESIS OF OLIGONUCLEOTIDES BY THE PHOSPHORAMIDITE APPROACH [J].
BEAUCAGE, SL ;
IYER, RP .
TETRAHEDRON, 1992, 48 (12) :2223-2311
[4]   Cholesterol recognition and binding by cyclodextrin dimers [J].
Breslow, R ;
Zhang, BL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (35) :8495-8496
[5]  
Curran DP, 2001, SYNLETT, P1488
[6]  
DANDAPANI S, 2004, TETRAHEDRON LETT, P45
[7]   A STRATEGY FOR THE SOLID-PHASE SYNTHESIS OF OLIGOSACCHARIDES [J].
DANISHEFSKY, SJ ;
MCCLURE, KF ;
RANDOLPH, JT ;
RUGGERI, RB .
SCIENCE, 1993, 260 (5112) :1307-1309
[8]   Soluble polymers as scaffolds for recoverable catalysts and reagents [J].
Dickerson, TJ ;
Reed, NN ;
Janda, KD .
CHEMICAL REVIEWS, 2002, 102 (10) :3325-3343
[9]   Design, synthesis, and evaluation of small-molecule libraries [J].
Ellman, JA .
ACCOUNTS OF CHEMICAL RESEARCH, 1996, 29 (03) :132-143
[10]  
MATSUI Y, 1985, TOP CURR CHEM, V128, P61