A highly stable, six-hydrogen-bonded molecular duplex

被引：201

作者：

Zeng, HQ ^{[1
]}

Miller, RS ^{[1
]}

Flowers, RA ^{[1
]}

Gong, B ^{[1
]}

机构：

[1] Univ Toledo, Dept Chem, Toledo, OH 43606 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2000年 / 122卷 / 11期

关键词：

D O I：

10.1021/ja9942742

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

This paper describes the design, synthesis, and characterization of a hydrogen-bonded molecular duplex (3.4). Two oligoamide molecular strands, 3 and 4, with the complementary hydrogen-bonding sequences ADAADA and DADDAD, respectively, were found to form an extremely stable (K-a = (1.3 +/- 0.7) x 10(9) M-1) molecular duplex (3.4) in chloroform. Evidence from 1D and 2D H-1 NMR spectroscopy, isothermal titration calorimetry, and thin-layer chromatography confirmed the formation and the high stability of the duplex. The exceptional stability is explained by positive cooperativity among the numerous hydrogen-bonding and van der Waals interactions and the preorganization of the individual strands by intramolecular hydrogen bonds. This design has opened a new avenue to supramolecular recognition units with programmable specificities and stabilities.

引用

页码：2635 / 2644

页数：10

共 45 条

[1] Strong dimerization of ureidopyrimidones via quadruple hydrogen bonding [J].