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Published on: August 2, 2012
The influence of molecular conformation upon the self-assembly of cyclohexane diamide diacids
R J Bergeron1, G W Yao, G W Erdos
1Department of Medicinal Chemistry, University of Florida, J. Hillis Miller Health Center, Gainesville 32610, USA.
Background:
Information regarding the self-association of small peptide motifs can be used in the design of peptide microstructures. Previous work in our laboratories illustrated the self-association of certain diamide diacids into microcapsules. In this report a series of cyclohexane diamide diacids are investigated. The cyclohexylene (R-C6H10-R) system (with its axial and equatorial requirements) provided an opportunity to study the influence of molecular conformation upon the self-aggregation process.
Results:
Condensation of the respective cis- and trans-1,2-, 1,3-, and 1,4- cyclohexane dicarboxylic acid platforms with two equivalents of a L-Phe ester followed by deprotection gave the desired diamide diacids. Basic solutions of cis-1,2-, trans-1,3-, and cis-1,4-diamide diacids generated solid microspheres when acidified to pH 2.4. Molecular modeling revealed that 1,3-diaxial interactions favor a helical turn within these diamides.
Conclusions:
Access to 'complementary' molecular geometries is needed to self-associate into microscopic architectures.
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