Molecular “Chaperones” Guide the Spontaneous Formation of a 15-Component Hydrogen-Bonded Assembly

Chaperones are small molecules that assist in the folding of naturally occurring peptides. There are no examples of small molecules acting as chaperones in the self-assembly of synthetic noncovalent assemblies. In this communication we describe an unprecedented example of the “chaperone effect” in t...

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Bibliographic Details
Published in:Journal of the American Chemical Society 2002-07, Vol.124 (26), p.7638-7639
Main Authors: Paraschiv, Vasile, Crego-Calama, Mercedes, Ishi-i, Tsutomu, Padberg, Clemens J, Timmerman, Peter, Reinhoudt, David N
Format: Article
Language:English
Subjects:
Barbiturates - chemistry
Chemistry
Exact sciences and technology
General and physical chemistry
Hydrogen Bonding
Kinetics
Magnetic Resonance Spectroscopy
Molecular Chaperones - chemistry
Molecular Mimicry
Solution properties
Solutions
Triazines - chemistry
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Summary:Chaperones are small molecules that assist in the folding of naturally occurring peptides. There are no examples of small molecules acting as chaperones in the self-assembly of synthetic noncovalent assemblies. In this communication we describe an unprecedented example of the “chaperone effect” in the noncovalent synthesis of organic nanostructures. Tetrarosette assemblies 2 3·(BuCYA)12 form quantitatively in CHCl3 at room temperature upon mixing tetramelamine 2 with N-butylcyanurate (BuCYA) in the presence of 5,5-diethylbarbituric acid (DEB). Without the DEB units present, only oligomeric assemblies are formed that cannot rearrange to the tetrarosettes by themselves. The DEB units act as molecular “chaperones” by preorganizing the tetramelamine units for the spontaneous assembly of the tetrarosette structure.
ISSN:0002-7863
1520-5126
DOI:10.1021/ja012384e