CONVERGENT FUNCTIONAL-GROUPS .10. MOLECULAR RECOGNITION OF NEUTRAL SUBSTRATES

被引：145

作者：

JEONG, KS ^{[1
]}

TJIVIKUA, T ^{[1
]}

MUEHLDORF, A ^{[1
]}

DESLONGCHAMPS, G ^{[1
]}

FAMULOK, M ^{[1
]}

REBEK, J ^{[1
]}

机构：

[1] MIT,DEPT CHEM,CAMBRIDGE,MA 02139

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 1991年 / 113卷 / 01期

关键词：

D O I：

10.1021/ja00001a029

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

In this paper synthetic molecular clefts with functional groups complementary to adenines, diketopiperazines, and barbiturates are described. Lactams and imides are compared for hydrogen-bonding affinities toward each other and to the heterocycles mentioned above. Titrations in CDCl3 using NMR show association constants vary by factors of 10(4) for adenines, 10(2) for diketopiperazines, and 10 for barbiturates with the new receptors. Enantioselective recognition of cycclo-L-Leu-Leu is observed, corresponding to DELTA DELTA-G = 2.7 kcal/mol. The relative strengths of hydrogen-bonding arrays are interpreted in terms of secondary interactions such as defined in the following paper in this issue by Jorgensen and Severance.

引用

页码：201 / 209

页数：9

共 26 条

[1] MOLECULAR RECOGNITION WITH CONVERGENT FUNCTIONAL-GROUPS .6. SYNTHETIC AND STRUCTURAL STUDIES WITH A MODEL RECEPTOR FOR NUCLEIC-ACID COMPONENTS [J].