Convergent Functional Groups. 10. Molecular Recognition of Neutral Substrates

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

Research output: Contribution to journalArticle

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 languageEnglish
Pages (from-to)201-209
Number of pages9
JournalJournal of the American Chemical Society
Volume113
Issue number1
DOIs
Publication statusPublished - 1991 Jan 1

Fingerprint

Diketopiperazines
Molecular recognition
Barbiturates
Adenine
Hydrogen Bonding
Functional groups
Hydrogen bonds
leucylleucine
Imides
Lactams
Substrates
Titration
Nuclear magnetic resonance
Association reactions

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

Cite this

Jeong, Kyu-Sung ; Tjivikua, T. ; Muehldorf, A. ; Deslongchamps, G. ; Famulok, M. ; Rebek, J. / Convergent Functional Groups. 10. Molecular Recognition of Neutral Substrates. In: Journal of the American Chemical Society. 1991 ; Vol. 113, No. 1. pp. 201-209.
@article{ed9a2c700a4a4100bc567a315a6cd766,
title = "Convergent Functional Groups. 10. Molecular Recognition of Neutral Substrates",
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.",
author = "Kyu-Sung Jeong and T. Tjivikua and A. Muehldorf and G. Deslongchamps and M. Famulok and J. Rebek",
year = "1991",
month = "1",
day = "1",
doi = "10.1021/ja00001a029",
language = "English",
volume = "113",
pages = "201--209",
journal = "Journal of the American Chemical Society",
issn = "0002-7863",
publisher = "American Chemical Society",
number = "1",

}

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, vol. 113, no. 1, pp. 201-209. https://doi.org/10.1021/ja00001a029

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 journalArticle

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.

UR - http://www.scopus.com/inward/record.url?scp=0000082688&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0000082688&partnerID=8YFLogxK

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 -