Title

The influence of molecular conformation upon the self-assembly of cyclohexane diamide diacids

Keywords

Conformation; Microspheres; Molecular recognition; Self-assembly

Abstract

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.

Publication Date

11-1-1997

Publication Title

Bioorganic and Medicinal Chemistry

Volume

5

Issue

11

Number of Pages

2049-2061

Document Type

Article

Personal Identifier

scopus

DOI Link

https://doi.org/10.1016/S0968-0896(97)00139-9

Socpus ID

0342872026 (Scopus)

Source API URL

https://api.elsevier.com/content/abstract/scopus_id/0342872026

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