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 | |
| Publication status | Published - 1991 Jan 1 |
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All Science Journal Classification (ASJC) codes
- Catalysis
- Chemistry(all)
- Biochemistry
- Colloid and Surface Chemistry
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Convergent Functional Groups. 10. Molecular Recognition of Neutral Substrates. / Jeong, Kyu-Sung; Tjivikua, T.; Muehldorf, A.; Deslongchamps, G.; Famulok, M.; Rebek, J.
In: Journal of the American Chemical Society, Vol. 113, No. 1, 01.01.1991, p. 201-209.Research output: Contribution to journal › Article
TY - JOUR
T1 - Convergent Functional Groups. 10. Molecular Recognition of Neutral Substrates
AU - Jeong, Kyu-Sung
AU - Tjivikua, T.
AU - Muehldorf, A.
AU - Deslongchamps, G.
AU - Famulok, M.
AU - Rebek, J.
PY - 1991/1/1
Y1 - 1991/1/1
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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U2 - 10.1021/ja00001a029
DO - 10.1021/ja00001a029
M3 - Article
VL - 113
SP - 201
EP - 209
JO - Journal of the American Chemical Society
JF - Journal of the American Chemical Society
SN - 0002-7863
IS - 1
ER -