Molecular diversity of novel amino acid based dendrimers

Mulders, S.J.E., Brouwer, A.J. and Liskamp, R.M.J. (1997) Molecular diversity of novel amino acid based dendrimers. Tetrahedron Letters, 38(17), pp. 3085-3088. (doi:10.1016/S0040-4039(97)00551-0)

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Abstract

We have expanded the recently introduced methodology for the preparation of a novel amino acid based dendrimer in order to be able to synthesize a diversity of dendrimers. For this purpose different hydroxybenzoic acids and amino alcohols were used to prepare the required monomers, necessary for construction of the respective dendrimers. © 1997 Elsevier Science Ltd. In the preparation of the first molecules to be named (starbust) dendrimers advantage was taken from the formation of the stable amide bond, [1] leading to defined macromolecules ultimately containing several hundreds of amide bonds, i.e. as many as there are present in proteins. Not surprisingly, a significant number of subsequent dendrimer syntheses featured the repeated formation of amide bonds in their construction. [2] In a previous communication we have described the efficient synthesis of a novel amino acid based dendrimer [3]. The BOP coupling reagent, [4] normally used in high-yielding and clean syntheses of peptides, was employed for the preparation of this particular dendrimer. In addition to the development of a reliable strategy for efficient construction of novel amino acid based dendrimers, it was our wish to introduce a considerable degree of molecular diversity in our dendrimer synthetic strategy, so that it could be employed for the preparation - in the future also by combinatorial methods - of dendrimers with a variety of branching patters, interior cavity size, interior and surface functionality. We realized that a significant molecular diversity of dendrimers could be generated by using aromatic residues bearing varying numbers of amino and carboxylic acid functions. On their turn, these amino acid building blocks can be derived from various commercially available hydroxy benzoic acid derivatives and amino alcohol derivatives, which are either commercially available or easily synthetically accessible. A few representative examples of amino acid based dendrimer monomers containing a substituted aromatic residue are schematically depicted in Fig. 1. From this figure it also follows that already twelve different (homo)dendrimer monomers are possible by combination of the four depicted hydroxy benzoic acid derivatives and the three shown amino alcohols.

Item Type:Articles
Status:Published
Refereed:Yes
Glasgow Author(s) Enlighten ID:Liskamp, Professor Robert
Authors: Mulders, S.J.E., Brouwer, A.J., and Liskamp, R.M.J.
College/School:College of Science and Engineering > School of Chemistry
Journal Name:Tetrahedron Letters
ISSN:0040-4039
ISSN (Online):1873-3581

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