(S)-Histidine:: the ideal precursor for a novel family of chiral aminoacid and peptidic ionic liquids

被引：51

作者：

Guillen, F

Brégeon, D

Plaquevent, JC

机构：

[1] Univ Rouen, IRCOF, UMR 6014, CNRS, F-76821 Mont St Aignan, France

[2] Univ Caen, ENSICAEN, LCMT, CNRS,UMR 6507, F-14050 Caen, France

来源：

TETRAHEDRON LETTERS | 2006年 / 47卷 / 08期

关键词：

histidine; aminoacid; peptide; chiral ionic liquid; imidazolium;

D O I：

10.1016/j.tetlet.2005.12.090

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

(S)-Histidine is shown to be a powerful chiral precursor for the construction of a new series of imidazolium-containing chiral ionic liquids, in which the chiral bifunctional unit of the aminoacid remains unchanged. These ionic materials can be used as building blocks for the synthesis of peptidic ionic liquids. (c) 2006 Elsevier Ltd. All rights reserved.

引用

收藏

页码：1245 / 1248

页数：4

相关论文

共 17 条

[1] Synthesis of chiral ionic liquids from natural amino acids [J].

Bao, WL ;

Wang, ZM ;

Li, YX .

JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (02) :591-593

[2] Chiral ionic liquids, a renewal for the chemistry of chiral solvents?: Design, synthesis and applications for chiral recognition and asymmetric synthesis [J].

Baudequin, C ;

Brégeon, D ;

Levillain, J ;

Guillen, F ;

Plaquevent, JC ;

Gaumont, AC .

TETRAHEDRON-ASYMMETRY, 2005, 16 (24) :3921-3945

[3] Ionic liquids and chirality: opportunities and challenges [J].

Baudequin, C ;

Baudoux, J ;

Levillain, J ;

Cahard, D ;

Gaumont, AC ;

Plaquevent, JC .

TETRAHEDRON-ASYMMETRY, 2003, 14 (20) :3081-3093

[4] Design and synthesis of novel ionic liquid/liquid crystals (IL 2Cs) with axial chirality [J].

Baudoux, J ;

Judeinstein, P ;

Cahard, D ;

Plaquevent, JC .

TETRAHEDRON LETTERS, 2005, 46 (07) :1137-1140

[5]

BOSMANN A, 2001, Patent No. 1003708

[6]

BREGEON D, IN PRESS ACS S SER

[7] PHENACYL-DIRECTED ALKYLATION OF IMIDAZOLES - A NEW REGIOSPECIFIC SYNTHESIS OF 3-SUBSTITUTED L-HISTIDINES [J].

CHIVIKAS, CJ ;

HODGES, JC .

JOURNAL OF ORGANIC CHEMISTRY, 1987, 52 (16) :3591-3594

[8] Design and synthesis of imidazolinium salts derived from (L)-valine. Investigation of their potential in chiral molecular recognition [J].

Clavier, H ;

Boulanger, L ;

Audic, N ;

Toupet, L ;

Mauduit, M ;

Guillemin, JC .

CHEMICAL COMMUNICATIONS, 2004, (10) :1224-1225

[9] Chiral ionic liquids: Synthesis and applications [J].

Ding, J ;

Armstrong, DW .

CHIRALITY, 2005, 17 (05) :281-292

[10] Room temperature ionic liquids from 20 natural amino acids [J].

Fukumoto, K ;

Yoshizawa, M ;

Ohno, H .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (08) :2398-2399