Synthesis and binding properties of a macrocycle with two binding subcavities

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

doi:10.1016/j.tetlet.2006.04.078

Synthesis and binding properties of a macrocycle with two binding subcavities

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

Department of Chemistry

Research output: Contribution to journal › Article › peer-review

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 language	English
Pages (from-to)	4141-4144
Number of pages	4
Journal	Tetrahedron Letters
Volume	47
Issue number	25
DOIs	https://doi.org/10.1016/j.tetlet.2006.04.078
Publication status	Published - 2006 Jun 19

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title = "Synthesis and binding properties of a macrocycle with two binding subcavities",

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.",

author = "Kyu-Sung Jeong and Kyoung-Jin Chang and Hye-Young Jang",

year = "2006",

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doi = "10.1016/j.tetlet.2006.04.078",

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journal = "Tetrahedron Letters",

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T1 - Synthesis and binding properties of a macrocycle with two binding subcavities

AU - Jeong, Kyu-Sung

AU - Chang, Kyoung-Jin

AU - Jang, Hye-Young

PY - 2006/6/19

Y1 - 2006/6/19

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.

AB - 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.

U2 - 10.1016/j.tetlet.2006.04.078

DO - 10.1016/j.tetlet.2006.04.078

M3 - Article

SN - 0040-4039

VL - 47

SP - 4141

EP - 4144

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 25

ER -

Synthesis and binding properties of a macrocycle with two binding subcavities

Abstract

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