Solid‐phase synthesis of second‐generation polyproline dendrimers

Abstract

Second-generation dendrimers have been prepared on solid phase by successive additions of branched polyproline building blocks starting from two different branching units anchored to the solid support. The preparation of Pro-rich building blocks was carried out by stepwise solid-phase synthesis and their iterative addition was performed by a convergent approach, also using solid-phase synthesis. cis-4-Amino-L-proline and imidazolidine-2-carboxylic acid were used as branching units due to their structural resemblance to proline. The optimized strategy allowed the target compounds to be obtained with high purities without the need for purification steps.

Synthesis and screening of a small library of proline‐based biodendrimers for use as delivery agents

“…38 Both linear and dendritic polyprolines were found to be actively internalized by rat kidney cells (NRK-49F). Taking into account these preliminary results of translocation efficiency [Crespo et al 37 and unpublished data, presented at the 27th European Peptide Symposium, Italy, 2000] for the case of dendrimers 1, 2, and 3, positively charged groups were introduced to develop carriers able to be internalized and to interact with polyanions such as DNA or oligonucleotides.…”

“…[36][37][38] All dendrimers consisted of a second-generation dendritic template from proline sequences. Dendrimers surfaces were then modified with different positively charged groups.…”

Amino Acid‐Based Dendrimers

“…A number of other peptide dendrimers composed of glutamic/aspartic acid [19][20][21][22][23], proline [8,[24][25][26], or arginine [27][28][29] have been reported. Ranganathan et al synthesized several series of polyglutamic/aspartic acid dendrimers including those with adamantane, an oxalyl group, or a benzenetricarbonyl unit as dendrimer core (Scheme 15.3) [19][20][21].…”

Peptide dendrimers

“…In most cases, MAPs have branches from lysine [11,86], but proline MAPs ( Figure 6) [90,91] and ornithine MAPs ( Figure 7) [92] are also known. For a review on polyglutamic, valine, leucine, arginine and depsipeptide dendrimers see Ref.…”