Convergent Functional Groups. 10. Molecular Recognition of Neutral Substrates

Kyu-Sung Jeong; T. Tjivikua; A. Muehldorf; G. Deslongchamps; M. Famulok; J. Rebek

doi:10.1021/ja00001a029

Convergent Functional Groups. 10. Molecular Recognition of Neutral Substrates

Kyu-Sung Jeong, T. Tjivikua, A. Muehldorf, G. Deslongchamps, M. Famulok, J. Rebek

Department of Chemistry

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134 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

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All Science Journal Classification (ASJC) codes

Catalysis
Chemistry(all)
Biochemistry
Colloid and Surface Chemistry

Cite this

Jeong, K-S., Tjivikua, T., Muehldorf, A., Deslongchamps, G., Famulok, M., & Rebek, J. (1991). Convergent Functional Groups. 10. Molecular Recognition of Neutral Substrates. Journal of the American Chemical Society, 113(1), 201-209. https://doi.org/10.1021/ja00001a029

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10.1021/ja00001a029