Synthesis and binding properties of a macrocycle with two binding subcavities

Kyu-Sung Jeong, Kyoung-Jin Chang, Hye-Young Jang

Research output: Contribution to journalArticle

5 Citations (Scopus)

Abstract

A large, covalent macrocycle that can be served as an artificial allosteric model was prepared in a reasonable yield (36%) through the template-directed synthesis. The macrocycle contains two topologically discrete subcavities, each of which consists of four amide NHs of pyridine-2,6-dicarboxamide units. The macrocycle strongly binds two molecules of N,N,N′,N′-tetramethylterephthalamide in positive cooperative manner by hydrogen-bonding interactions. The association constants were calculated to be K1 = 1480 ± 90 and K2 = 5580 ± 150 M−1 with the Hill coefficient (h) of 1.6 at 25 °C in CDCl3.
Original languageEnglish
Pages (from-to)4141-4144
Number of pages4
JournalTetrahedron Letters
Volume47
Issue number25
DOIs
Publication statusPublished - 2006 Jun 19

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