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Synthesis of Glycodendrimers by Modification of Poly(propylene imine) Dendrimers
Author(s) -
Ashton Peter R.,
Boyd Sue E.,
Brown Christopher L.,
Nepogodiev Sergey A.,
Meijer E. W.,
Peerlings H. W. I.,
Peerlings H. W. I.,
Stoddart J. Fraser
Publication year - 1997
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.19970030620
Subject(s) - dendrimer , chemistry , polymer chemistry , amide , imine , stereochemistry , organic chemistry , combinatorial chemistry , catalysis
Abstract The use of preformed poly‐(propylene imine) dendrimers (DAB‐ dendr ‐(NH 2 ) x ) for the rapid and facile construction of high molecular weight carbohydrate‐coated dendrimers (glyco‐dendrimers) is presented. An efficient attachment of spacer‐armed derivatives of D‐galactose and lactose to the primary amino end groups of DAB‐ dendr ‐(NH 2 ) x has been achieved by means of amide bond formation, using the N ‐hydroxysuccinimide coupling procedure. Acetate protecting groups have been employed in order to avoid side reactions at the coupling stage. Deacetylation leads to the target glycodendrimers. The reactivity of all the available DAB‐ dendr ‐(NH 2 ) x (generations 1–5) has been investigated and a series of homologous carbohydrate‐coated dendrimers have been synthesized. In addition, the attachment of larger saccharide moieties has been demonstrated by the condensation of a trisgalactoside cluster with DAB‐ dendr ‐(NH 2 ) x carrying both four and eight primary amino groups. The regularity of the glycodendrimers has been proven by NMR spectroscopy, and the molecular weights of the low‐generation carbohydrate‐coated dendrimers have been determined by mass spectrometry. Modifications of DAB‐ dendr ‐(NH 2 ) x with biologically active carbohydrates affords a new and simple approach to high molecular weight compounds that may be considered as neoglycoconjugates with perfectly symmetrical structures and that offer much promise as multivalent ligands involved in carbohydrate‐protein interactions.