Fluorous substituent-based enantiomer and diastereomer separation: Orthogonal use of HPLC columns for the synthesis of nonproteinogenic polyfluoro amino acids and peptides

被引:21
作者
Tonoi, Takayuki [1 ]
Nishikawa, Aya [1 ]
Yajima, Tomoko [1 ]
Nagano, Hajime [1 ]
Mikami, Koichi [2 ]
机构
[1] Ochanomizu Univ, Dept Chem, Tokyo 1128610, Japan
[2] Tokyo Inst Technol, Dept Appl Chem, Tokyo 1528552, Japan
关键词
fluorine; racemates; amino acids; peptides;
D O I
10.1002/ejoc.200701052
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
variety of fluorine-containing amino acid and dipeptide precursors bearing different lengths of perfluoroalkyl chains were separated into their enantiorners and diastereomers, respectively, by the orthogonal use of fluorous and chiral HPLC columns. These results show the applicability of fluorous racemic mixture synthesis for various "fluorinated" chiral products without introducing conventional cleavable fluorous tags. ((c) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008).
引用
收藏
页码:1331 / 1335
页数:5
相关论文
共 39 条
[1]   Methodologies for generating solution-phase combinatorial libraries [J].
An, HY ;
Cook, PD .
CHEMICAL REVIEWS, 2000, 100 (09) :3311-3340
[2]  
Bein T, 1999, ANGEW CHEM INT EDIT, V38, P323, DOI 10.1002/(SICI)1521-3773(19990201)38:3<323::AID-ANIE323>3.0.CO
[3]  
2-4
[4]  
BEIN T, 1999, ANGEW CHEM, V111, P335
[5]  
Curran D. P., 2006, ANGEW CHEM, V118, P2483
[6]   Solution-phase mixture synthesis with fluorous tagging en route: Total synthesis of an eight-member stereoisomer library of passifloricins [J].
Curran, DP ;
Moura-Letts, G ;
Pohlman, M .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (15) :2423-2426
[7]  
CURRAN DP, 2004, HDB FLUOROUS CHEM, pCH8
[8]  
CURRAN DP, 2005, GREEN REACTION MEDIA
[9]   Mixture-based synthetic combinatorial libraries [J].
Houghten, RA ;
Pinilla, C ;
Appel, JR ;
Blondelle, SE ;
Dooley, CT ;
Eichler, J ;
Nefzi, A ;
Ostresh, JM .
JOURNAL OF MEDICINAL CHEMISTRY, 1999, 42 (19) :3743-3778
[10]   Fluorine in peptide design and protein engineering [J].
Jäckel, C ;
Koksch, B .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2005, 2005 (21) :4483-+