Convergent Functional Groups. 10. Molecular Recognition of Neutral Substrates

K. S. Jeong; T. Tjivikua; A. Muehldorf; G. Deslongchamps; M. Famulok; J. Rebek

doi:10.1021/ja00001a029

Convergent Functional Groups. 10. Molecular Recognition of Neutral Substrates

K. S. Jeong, T. Tjivikua, A. Muehldorf, G. Deslongchamps, M. Famulok, J. Rebek

Department of Chemistry

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136 Citations (Scopus)

Abstract

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 affinites toward each other and to the heterocycles mentioned above. Titrations in CDC1₃ using NMR show association constants vary by factors of 10⁴ for adenines, l0² for diketopiperazines, and 10 for barbiturates with the new receptors. Enantioselective recognition of cyc/o-L-Leu-Leu is observed, corresponding to ΔΔG = 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.

Original language	English
Pages (from-to)	201-209
Number of pages	9
Journal	Journal of the American Chemical Society
Volume	113
Issue number	1
DOIs	https://doi.org/10.1021/ja00001a029
Publication status	Published - 1991 Jan 1

All Science Journal Classification (ASJC) codes

Catalysis
Chemistry(all)
Biochemistry
Colloid and Surface Chemistry

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abstract = "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 affinites toward each other and to the heterocycles mentioned above. Titrations in CDC13 using NMR show association constants vary by factors of 104 for adenines, l02 for diketopiperazines, and 10 for barbiturates with the new receptors. Enantioselective recognition of cyc/o-L-Leu-Leu is observed, corresponding to ΔΔG = 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.",

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AU - Jeong, K. S.

AU - Tjivikua, T.

AU - Muehldorf, A.

AU - Deslongchamps, G.

AU - Famulok, M.

AU - Rebek, J.

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N2 - 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 affinites toward each other and to the heterocycles mentioned above. Titrations in CDC13 using NMR show association constants vary by factors of 104 for adenines, l02 for diketopiperazines, and 10 for barbiturates with the new receptors. Enantioselective recognition of cyc/o-L-Leu-Leu is observed, corresponding to ΔΔG = 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.

AB - 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 affinites toward each other and to the heterocycles mentioned above. Titrations in CDC13 using NMR show association constants vary by factors of 104 for adenines, l02 for diketopiperazines, and 10 for barbiturates with the new receptors. Enantioselective recognition of cyc/o-L-Leu-Leu is observed, corresponding to ΔΔG = 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.

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Convergent Functional Groups. 10. Molecular Recognition of Neutral Substrates

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