Bile acid scaffolds in supramolecular chemistry: The interplay of design and synthesis

被引:80
作者
Davis, Anthony P. [1 ]
机构
[1] Univ Bristol, Sch Chem, Bristol BS8 1TS, Avon, England
来源
MOLECULES | 2007年 / 12卷 / 09期
关键词
supramolecular chemistry; steroids; anion recognition; carbohydrate; recognition; stereoselective synthesis;
D O I
10.3390/12082106
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
Since early work in the 1980s, the bile acids have become well established as building blocks for supramolecular chemistry. The author's laboratory has specialised in converting cholic acid, the archetypal bile acid, into macrocyclic and acyclic receptors for anions and carbohydrates. This review highlights the synthetic aspects of this work, especially the use of modem synthetic methodology to perform less obvious structural transformations.
引用
收藏
页码:2106 / 2122
页数:17
相关论文
共 53 条
[1]  
Ayling AJ, 2002, CHEM-EUR J, V8, P2197, DOI 10.1002/1521-3765(20020503)8:9<2197::AID-CHEM2197>3.0.CO
[2]  
2-J
[3]   New "cholapod" anionophores; high-affinity halide receptors derived from cholic acid [J].
Ayling, AJ ;
Pérez-Payán, MN ;
Davis, AP .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (50) :12716-12717
[4]  
Baragaña B, 2002, CHEM-EUR J, V8, P2931, DOI 10.1002/1521-3765(20020703)8:13<2931::AID-CHEM2931>3.0.CO
[5]  
2-H
[6]   A trifunctional steroid-based scaffold for combinatorial chemistry [J].
Barry, JF ;
Davis, AP ;
Perez-Payas, MN ;
Elsegood, MRJ ;
Jackson, RFW ;
Gennari, C ;
Piarulli, U ;
Gude, M .
TETRAHEDRON LETTERS, 1999, 40 (14) :2849-2852
[7]  
BARTON DHR, 1989, TETRAHEDRON, V45, P3741
[8]   The "triamino-analogue'' of methyl allocholate; a rigid, functionalised scaffold for supramolecular chemistry [J].
Bhattarai, Khadga M. ;
del Amo, Vicente ;
Magro, Germinal ;
Sisson, Adam L. ;
Joos, Jean-Baptiste ;
Charmant, Jonathan P. H. ;
Kantacha, Anob ;
Davis, Anthony P. .
CHEMICAL COMMUNICATIONS, 2006, (22) :2335-2337
[9]   A new generation of ''cholaphanes'': Steroid-derived macrocyclic hosts with enhanced solubility and controlled flexibility [J].
Bhattarai, KM ;
Davis, AP ;
Perry, JJ ;
Walter, CJ ;
Menzer, S ;
Williams, DJ .
JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (24) :8463-8473
[10]   SYNTHESIS OF STEROIDAL CYCLODIMERS FROM CHOLIC-ACID - A MOLECULAR FRAMEWORK WITH POTENTIAL FOR RECOGNITION AND CATALYSIS [J].
BONARLAW, RP ;
DAVIS, AP .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1989, (15) :1050-1052