Aromatic oligoureas: Enforced folding and assisted cyclization

被引:76
作者
Zhang, AM [1 ]
Han, YH
Yamato, K
Zeng, XC
Gong, B
机构
[1] SUNY Buffalo, Dept Chem, Buffalo, NY 14260 USA
[2] Univ Nebraska, Dept Chem, Lincoln, NE 68588 USA
关键词
D O I
10.1021/ol0526322
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Aromatic oligoureas are forced into well-defined conformation by incorporated intramolecular hydrogen bonds. Shape-persistent tetraureas macrocycles were obtained in a one-step [2 + 2] reaction in good yields.
引用
收藏
页码:803 / 806
页数:4
相关论文
共 16 条
[1]   Interconversion of single and double helices formed from synthetic molecular strands [J].
Berl, V ;
Huc, I ;
Khoury, RG ;
Krische, MJ ;
Lehn, JM .
NATURE, 2000, 407 (6805) :720-723
[2]  
BOCIJEN A, 1999, EUR J ORG CHEM, P2127
[3]   Complexation-induced unfolding of heterocyclic ureas. Simple foldamers equilibrate with multiply hydrogen-bonded sheetlike structures [J].
Corbin, PS ;
Zimmerman, SC ;
Thiessen, PA ;
Hawryluk, NA ;
Murray, TJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (43) :10475-10488
[4]   Foldamers: A manifesto [J].
Gellman, SH .
ACCOUNTS OF CHEMICAL RESEARCH, 1998, 31 (04) :173-180
[5]  
Gong B, 2001, CHEM-EUR J, V7, P4336, DOI 10.1002/1521-3765(20011015)7:20<4336::AID-CHEM4336>3.0.CO
[6]  
2-1
[7]   Oligoanthranilamides. Non-peptide subunits that show formation of specific secondary structure [J].
Hamuro, Y ;
Geib, SJ ;
Hamilton, AD .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (32) :7529-7541
[8]   A field guide to foldamers [J].
Hill, DJ ;
Mio, MJ ;
Prince, RB ;
Hughes, TS ;
Moore, JS .
CHEMICAL REVIEWS, 2001, 101 (12) :3893-4011
[9]   Aromatic oligoamide foldamers [J].
Huc, I .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2004, 2004 (01) :17-29
[10]   Aromatic δ-peptides:: design, synthesis and structural studies of helical, quinoline-derived oligoamide foldamers [J].
Jiang, H ;
Léger, JM ;
Dolain, C ;
Guionneau, P ;
Huc, I .
TETRAHEDRON, 2003, 59 (42) :8365-8374