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Triurea Derivatives of Diethylenetriamine as Potential Templates for the Formation of Artificial β-Sheets1

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    Triurea Derivatives of Diethylenetriamine as Potential Templates for the Formation of Artificial β-Sheets1
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    Contribution from the Department of Chemistry, University of California, Irvine, Irvine, California 92717-2025
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    Journal of the American Chemical Society

    Cite this: J. Am. Chem. Soc. 1996, 118, 5, 1066–1072
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    https://doi.org/10.1021/ja9536072
    Published February 7, 1996
    Copyright © 1996 American Chemical Society
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    Abstract

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    This paper describes synthetic and structural studies of triurea derivatives of an N,N"-disubstituted diethylenetriamine. Diethylenetriamine triureas 1 (PhN(CONHR1)CH2CH2N(CONHR2)CH2CH2N(CONHR3)CH2CH2CN; 2a, R1 = R2 = R3 = Ph; 2b, R1 = R2 = R3 = CH3; 2c, R1 = (S)-CH(CH2Ph)CO2CH3, R2 = (S)-CH(i-Pr)CO2CH3, R3 = (S)-CH((S)-s-Bu)CO2CH3)) are efficiently prepared in five or six steps from N-phenylethylenediamine. Infrared spectroscopy, 1H NMR spectroscopy, and X-ray crystallography indicate that triureas 1 adopt intramolecularly hydrogen-bonded conformations, both in chloroform solution and in the solid state. The three urea groups form a hydrogen-bonded network:  The carbonyl group of urea NCONHR1 is hydrogen bonded to the NH group of urea NCONHR2, and the carbonyl group of urea NCONHR2 is hydrogen bonded to the NH group of urea NCONHR3. The three R groups are aligned along the triurea backbone, pointing in roughly the same direction, like three fingers on a hand. Molecular modeling suggests that the triurea backbone will be a suitable template for the creation of artificial β-sheets. When molecular mechanics energy minimization calculations are performed upon a triurea bearing three N-terminally linked peptide strands, a parallel β-sheet is formed.

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     Abstract published in Advance ACS Abstracts, January 15, 1996.

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    Experimental details of the X-ray crystallographic structure determination, tables of distances, angles, fractional coordinates, and thermal parameters, and thermal ellipsoid plots for triureas 1a, b (32 pages). This material is contained in many libraries on microfiche, immediately follows this article in the microfilm version of the journal, and can be ordered from the ACS, can be downloaded from the Internet; see any current masthead page for ordering information and Internet access instructions.

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    Cite this: J. Am. Chem. Soc. 1996, 118, 5, 1066–1072
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    https://doi.org/10.1021/ja9536072
    Published February 7, 1996
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