Title

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

Authors

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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