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Updated: Jul 17, 2026

Facile Protocol for the Synthesis of Self-assembling Polyamine-based Peptide Amphiphiles (PPAs) and Related Biomaterials
Published on: June 25, 2018
Synthesis and stereoselective DNA binding abilities of new optically active open-chain polyamines
Carmen Peña1, Ignacio Alfonso, Blake Tooth
1Departamento de Química Orgánica e Inorgánica, Facultad de Química, Universidad de Oviedo, Spain.
Abstract:
The efficient synthesis of new open-chain enantiopure polyamines bearing (R,R)- and/or (S,S)-trans-cyclohexane-1,2-diamine moieties is described. The key step for the synthetic procedure is the selective monoalkylation of the cyclohexanebis(sulfonamide) core, which allows the subsequent functionalization of this moiety. Compounds bearing different combinations of absolute configurations, length of the aliphatic spacers and terminal groups have been prepared. As a demonstration of the potential utility of the obtained compounds, the preliminary DNA binding abilities of some of them have been studied by UV-measurements of melting temperatures (Tm). The effects of the absolute configuration of the corresponding chiral centers and the length of the spacer separating the cyclohexanediamine moieties on the strength of the interaction with DNA are also discussed.
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