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Synthesis 2002(10): 1398-1406
DOI: 10.1055/s-2002-33116
PAPER
© Georg Thieme Verlag Stuttgart · New York

Convergent and Sequential Synthesis of Dendritic, Multivalent Complexing Agents

Cuihua Liu, Robert H. E. Hudson, Nils O. Petersen*
Department of Chemistry, The University of Western Ontario, London, Ontario, N6A 5B7 Canada
Fax: +1(19)6613022; e-Mail: petersen@uwo.ca;
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Publication History

Received 4 November 2001
Publication Date:
01 August 2002 (online)

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Abstract

Two series of macrocyclic polyamine derivatives with various length of linkers were synthesized as dendritic ligands containing two, three, four, five or six terminal nitrilotriacetic acid (NTA) groups through convergent and sequential pathways. Tetrafluorophenyl esters were employed as activating reagents in the coupling step of assembling NTA groups to the cyclic polyamine head. A key step of the sequential synthesis is the use of the coupling reagent, 2-(3,4-dihydro-4-oxo-1,2,3-benzotriazin-3-yl)-1,1,3,3-tetramethyluronium tetrafluoroborate (TBTU) for the formation of amide bonds between the cyclic polyamine and pendant groups. Finally, two representative compounds were used to demonstrate the formation of stoichiometric protein assemblies.

Key words

complexing agents - polyamines - coupling - nitrilotriacetic acid