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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Hydrogen Bonding
Amides
Hydrogen bonds
Association reactions
Molecules
pyridine-2,6-dicarboxamide

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Jeong, Kyu-Sung ; Chang, Kyoung-Jin ; Jang, Hye-Young. / Synthesis and binding properties of a macrocycle with two binding subcavities. In: Tetrahedron Letters. 2006 ; Vol. 47, No. 25. pp. 4141-4144.
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Synthesis and binding properties of a macrocycle with two binding subcavities. / Jeong, Kyu-Sung; Chang, Kyoung-Jin; Jang, Hye-Young.

In: Tetrahedron Letters, Vol. 47, No. 25, 19.06.2006, p. 4141-4144.

Research output: Contribution to journalArticle

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AU - Jeong, Kyu-Sung

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N2 - 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.

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