Hydrogen bonded oligohydrazide foldamers and their recognition for saccharides

被引:237
作者
Hou, JL
Shao, XB
Chen, GJ
Zhou, YX
Jiang, XK
Li, ZT
机构
[1] Chinese Acad Sci, Shanghai Inst Organ Chem, Shanghai 200032, Peoples R China
[2] Beijing Normal Univ, Dept Chem, Beijing 100875, Peoples R China
关键词
D O I
10.1021/ja047436p
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
This paper describes the synthesis and characterization of the first series of hydrogen bonding-driven hydrazide foldamers and their recognition for alkyl saccharides in chloroform. Oligomers 1, 2-4, 5, 6, and 7, which contain one, two, four, six, or twelve repeated dibenzoyl hydrazide residues, respectively, have been prepared. The rigid and planar conformations of 1 and 2 or 4 have been established with X-ray analysis and H-1 NMR spectroscopy, whereas the folding and helical conformations of 5-7 have been evidenced by the 1D and 2D H-1 NMR and IR spectroscopy and molecular mechanics calculations. Molecular mechanics calculations also revealed that 5, 6, and 7 possess a rigid cavity with size of ca. 10.6 to 11.1 Angstrom, and half of the carbonyl groups in the folding conformations are orientated inwardly inside the cavity. H-1 NMR and CD experiments revealed that 5-7 efficiently complex alkylated mono- and disaccharides 32-35 in chloroform. The association constants (K-assoc) of the complexes have been determined with the H-1 NMR and fluorescent titration methods. The energy-minimized conformation of 6(.)34 has been obtained with molecular mechanics calculation. The hydrazide-based folding structures described here represent novel examples of hydrogen bonding-driven foldamers that act as artificial receptors for selective molecular recognition.
引用
收藏
页码:12386 / 12394
页数:9
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共 92 条
[21]  
Gong B, 2001, CHEM-EUR J, V7, P4336, DOI 10.1002/1521-3765(20011015)7:20<4336::AID-CHEM4336>3.0.CO
[22]  
2-1
[23]   Creating nanocavities of tunable sizes: Hollow helices [J].
Gong, B ;
Zeng, HQ ;
Zhu, J ;
Yuan, LH ;
Han, YH ;
Cheng, SZ ;
Furukawa, M ;
Parra, RD ;
Kovalevsky, AY ;
Mills, JL ;
Skrzypczak-Jankun, E ;
Martinovic, S ;
Smith, RD ;
Zheng, C ;
Szyperski, T ;
Zeng, XC .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2002, 99 (18) :11583-11588
[24]   Fluorescent sensing of pyrophosphate and bis-carboxylates with charge neutral PET chemosensors [J].
Gunnlaugsson, T ;
Davis, AP ;
O'Brien, JE ;
Glynn, M .
ORGANIC LETTERS, 2002, 4 (15) :2449-2452
[25]   VINYLOGOUS POLYPEPTIDES - AN ALTERNATIVE PEPTIDE BACKBONE [J].
HAGIHARA, M ;
ANTHONY, NJ ;
STOUT, TJ ;
CLARDY, J ;
SCHREIBER, SL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (16) :6568-6570
[26]   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
[27]   Novel folding patterns in a family of oligoanthranilamides: Non-peptide oligomers that form extended helical secondary structures [J].
Hamuro, Y ;
Geib, SJ ;
Hamilton, AD .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (44) :10587-10593
[28]   Design of secondary structures in unnatural peptides:: Stable helical γ-tetra-, hexa-, and octapeptides and consequences of α-substitution [J].
Hanessian, S ;
Luo, XH ;
Schaum, R ;
Michnick, S .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1998, 120 (33) :8569-8570
[29]   Folding-promoted methylation of a helical DMAP analogue [J].
Heemstra, JM ;
Moore, JS .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (06) :1648-1649
[30]   A field guide to foldamers [J].
Hill, DJ ;
Mio, MJ ;
Prince, RB ;
Hughes, TS ;
Moore, JS .
CHEMICAL REVIEWS, 2001, 101 (12) :3893-4011