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Facile Protocol for the Synthesis of Self-assembling Polyamine-based Peptide Amphiphiles PPAs and Related Biomaterials
Published on: June 25, 2018
Tetrazole as a Carboxylic Acid Isostere and the Synthesis of All Amine-Based Polyampholytes
Amber Nguyen1, Elena Dallerba1, Andrew B Lowe1
1School of Molecular and Life Sciences, Curtin University, Bentley, Perth, Western Australia, 6102, Australia.
Abstract:
A new family of polyampholytes (PAMs) is described in which both the basic and acidic groups are based on nitrogen functional groups. Reversible addition-fragmentation chain transfer-prepared poly(pentafluorophenyl acrylate) is quantitatively modified sequentially with 3-picolylamine and 5-aminotetrazole, yielding the new well-defined statistical PAMs. Successful formation of the PAMs is confirmed via a combination of 19 F and 13 C NMR spectroscopy and FTIR. Aqueous electrophoresis indicates isoelectric points (pI) between 2.9 and 4.4 depending on copolymer composition. However, the pI is somewhat insensitive to the copolymer composition, a feature attributed to the similarity of the pKa s of the acid tetrazole species and the conjugate acid of the pyridyl repeat units.
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