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

    Authors

    R. J. Bergeron; G. W. Yao; G. W. Erdos; S. Milstein; F. L. Gao; J. Rocca; W. R. Weimar; H. L. Price;O. Phanstiel

    Comments

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    Abbreviated Journal Title

    Bioorg. Med. Chem.

    Keywords

    conformation; microspheres; molecular recognition; self-assembly; MODEL; RECOGNITION; PROTEINS; PEPTIDE; ACID; Biochemistry & Molecular Biology; Chemistry, Medicinal; Chemistry, ; Organic

    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. (C) 1997 Elsevier Science Ltd.

    Journal Title

    Bioorganic & Medicinal Chemistry

    Volume

    5

    Issue/Number

    11

    Publication Date

    1-1-1997

    Document Type

    Article

    Language

    English

    First Page

    2049

    Last Page

    2061

    WOS Identifier

    WOS:A1997XJ21700024

    ISSN

    0968-0896

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