A molecular receptor that selectively binds dihydrogen phosphate

Tae Hoon Kwon; Kyu Sung Jeong

doi:10.1016/j.tetlet.2006.09.105

A molecular receptor that selectively binds dihydrogen phosphate

Tae Hoon Kwon, Kyu Sung Jeong

Department of Chemistry

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

61 Citations (Scopus)

Abstract

A dihydrogen phosphate-binding receptor (4) containing both hydrogen bond donors and acceptors has been prepared by incorporating two pyridyl units to a preorganized biindole scaffold. Receptor 4 strongly and selectively binds dihydrogen phosphate via multiple hydrogen bonds with an association constant (K_a) of 1.1 × 10⁵ M^-1 in CH₃CN at 22 ± 1 °C. The high selectivity toward the target anion over other anions is proven to be due to two additional hydrogen bonds between the phosphate hydroxyl groups and the pyridyl nitrogens, each of which increases the complex stability by the free energy of 1.6 kcal/mol. This result clearly demonstrates that a selective receptor for a polyprotic anion can be developed by combining both hydrogen bond donors and acceptors.

Original language	English
Pages (from-to)	8539-8541
Number of pages	3
Journal	Tetrahedron Letters
Volume	47
Issue number	48
DOIs	https://doi.org/10.1016/j.tetlet.2006.09.105
Publication status	Published - 2006 Nov 27

Bibliographical note

Funding Information:
This work was financially supported by a Korea Research Foundation Grant (KRF-2004-041-C00215) and the Center for Bioactive Molecular Hybrids (CBMH).

All Science Journal Classification (ASJC) codes

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2006.09.105

Cite this

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title = "A molecular receptor that selectively binds dihydrogen phosphate",

abstract = "A dihydrogen phosphate-binding receptor (4) containing both hydrogen bond donors and acceptors has been prepared by incorporating two pyridyl units to a preorganized biindole scaffold. Receptor 4 strongly and selectively binds dihydrogen phosphate via multiple hydrogen bonds with an association constant (Ka) of 1.1 × 105 M-1 in CH3CN at 22 ± 1 °C. The high selectivity toward the target anion over other anions is proven to be due to two additional hydrogen bonds between the phosphate hydroxyl groups and the pyridyl nitrogens, each of which increases the complex stability by the free energy of 1.6 kcal/mol. This result clearly demonstrates that a selective receptor for a polyprotic anion can be developed by combining both hydrogen bond donors and acceptors.",

author = "Kwon, {Tae Hoon} and Jeong, {Kyu Sung}",

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T1 - A molecular receptor that selectively binds dihydrogen phosphate

AU - Kwon, Tae Hoon

AU - Jeong, Kyu Sung

N1 - Funding Information: This work was financially supported by a Korea Research Foundation Grant (KRF-2004-041-C00215) and the Center for Bioactive Molecular Hybrids (CBMH).

PY - 2006/11/27

Y1 - 2006/11/27

N2 - A dihydrogen phosphate-binding receptor (4) containing both hydrogen bond donors and acceptors has been prepared by incorporating two pyridyl units to a preorganized biindole scaffold. Receptor 4 strongly and selectively binds dihydrogen phosphate via multiple hydrogen bonds with an association constant (Ka) of 1.1 × 105 M-1 in CH3CN at 22 ± 1 °C. The high selectivity toward the target anion over other anions is proven to be due to two additional hydrogen bonds between the phosphate hydroxyl groups and the pyridyl nitrogens, each of which increases the complex stability by the free energy of 1.6 kcal/mol. This result clearly demonstrates that a selective receptor for a polyprotic anion can be developed by combining both hydrogen bond donors and acceptors.

AB - A dihydrogen phosphate-binding receptor (4) containing both hydrogen bond donors and acceptors has been prepared by incorporating two pyridyl units to a preorganized biindole scaffold. Receptor 4 strongly and selectively binds dihydrogen phosphate via multiple hydrogen bonds with an association constant (Ka) of 1.1 × 105 M-1 in CH3CN at 22 ± 1 °C. The high selectivity toward the target anion over other anions is proven to be due to two additional hydrogen bonds between the phosphate hydroxyl groups and the pyridyl nitrogens, each of which increases the complex stability by the free energy of 1.6 kcal/mol. This result clearly demonstrates that a selective receptor for a polyprotic anion can be developed by combining both hydrogen bond donors and acceptors.

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A molecular receptor that selectively binds dihydrogen phosphate

Abstract

Bibliographical note

All Science Journal Classification (ASJC) codes

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