Document Detail

Synthesis of carbosilane dendritic wedges and their use for the construction of dendritic receptors.
MedLine Citation:
PMID:  16391763     Owner:  NLM     Status:  MEDLINE    
A divergent route for the synthesis of carbosilane wedges that contain either a bromine or amine as focal point has been developed. These new building blocks enable the construction of various core-functionalized carbosilane dendrimers. As a typical example carbosilane dendrimers up to the third generation containing a N,N',N''-1,3,5-benzenetricarboxamide core (G1-G3) have been synthesized. This new class of molecules has been studied as host molecules and they have been found to bind protected amino acids as guest molecules via hydrogen bonding interactions. A decrease in the association constants was observed for the higher generation dendritic hosts, which is attributed to the increased steric hindrance around the core where the binding site is located. The binding properties of the dendritic host molecules can be tuned by modifying the binding motif at the core of the carbosilane dendrimers. A higher association constant for N-CBZ-protected glutamic acid 1-methyl ester (5) was observed when the third generation N,N',N''-1,3,5-tris(L-alaninyl)benzenetricarboxamide core-functionalized carbosilane dendrimer (G3') was used as the host molecule compared to G3. Different association constants for the formation of the diastereomeric G3'.L-5(K=295 M(-1)) and G3'.(D-5)(2) (K=236 M(-1)) host-guest complexes were observed, pointing to a small enantioselective recognition effect. The difference between the association constants for the formation of the G3'.(L-5)(2) and G3'.(D-5)(2) host-guest complexes was much more pronounced, K=37 M(-1)versus K=10 M(-1), respectively.
Rieko van Heerbeek; Paul C J Kamer; Piet N M W van Leeuwen; Joost N H Reek
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Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't     Date:  2005-12-14
Journal Detail:
Title:  Organic & biomolecular chemistry     Volume:  4     ISSN:  1477-0520     ISO Abbreviation:  Org. Biomol. Chem.     Publication Date:  2006 Jan 
Date Detail:
Created Date:  2006-01-04     Completed Date:  2007-06-06     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  101154995     Medline TA:  Org Biomol Chem     Country:  England    
Other Details:
Languages:  eng     Pagination:  211-23     Citation Subset:  IM    
Van't Hoff Institute for Molecular Sciences, University of Amsterdam, Nieuwe Achtergracht 166, 1018 WV Amsterdam, The Netherlands.
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MeSH Terms
Amino Acids / chemistry,  metabolism
Binding Sites
Dendrimers / chemical synthesis*
Hydrogen Bonding
Silanes / chemical synthesis*
Reg. No./Substance:
0/Amino Acids; 0/Dendrimers; 0/Silanes; 0/carbosilane

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