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Self-Structuring in Water of Polyamidoamino Acids with Hydrophobic Side Chains Deriving from Natural α-Amino Acids

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Dipartimento di Chimica, Università degli Studi di Milano, via C. Golgi 19, 20133 Milano, Italy
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Istituto per lo Studio delle Macromolecole (CNR), Via E. Bassini 15, 20133 Milano, Italy
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Dipartimento di Chimica, Materiali ed Ingegneria Chimica “G. Natta”, Politecnico di Milano, via L. Mancinelli 7, 20131 Milano, Italy
*
Authors to whom correspondence should be addressed.
Polymers 2018, 10(11), 1261; https://doi.org/10.3390/polym10111261
Received: 8 October 2018 / Revised: 31 October 2018 / Accepted: 11 November 2018 / Published: 13 November 2018
This paper reports on synthesis, acid-base properties and self-structuring in water of chiral polyamidoamino acids (PAACs) obtained by polyaddition of N,N′-methylenebisacrylamide with l-alanine, l-valine and l-leucine (M-l-Ala, M-l-Val, M-l-Leu) with potential for selective interactions with biomolecules. The polymers maintained the acid-base properties of amino acids. In water, the circular dichroism spectra of PAACs revealed pH-dependent structuring in the range 3–11 and in the wavelength interval 200–280 nm. Taking as reference the values at pH 3, the differential molar ellipticities were plotted in the pH interval 3–11. Sigmoidal curves were obtained presenting inflection points at pH 8.1, 6.8 and 7.3 for M-l-Ala, M-l-Val and M-l-Leu, respectively, corresponding to the amine half-ionization. Theoretical modeling showed that PAACs assumed stable folded conformations. Intramolecular interactions led to transoid arrangements of the main chain reminiscent of protein hairpin motif. Oligomers with ten repeat units had simulated gyration radii consistent with the hydrodynamic radii obtained by dynamic light scattering. View Full-Text
Keywords: polyamidoamino acid; self-structuring; pH-dependent circular dichroism; molecular dynamics; molecular simulations polyamidoamino acid; self-structuring; pH-dependent circular dichroism; molecular dynamics; molecular simulations
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MDPI and ACS Style

Lazzari, F.; Manfredi, A.; Alongi, J.; Mendichi, R.; Ganazzoli, F.; Raffaini, G.; Ferruti, P.; Ranucci, E. Self-Structuring in Water of Polyamidoamino Acids with Hydrophobic Side Chains Deriving from Natural α-Amino Acids. Polymers 2018, 10, 1261. https://doi.org/10.3390/polym10111261

AMA Style

Lazzari F, Manfredi A, Alongi J, Mendichi R, Ganazzoli F, Raffaini G, Ferruti P, Ranucci E. Self-Structuring in Water of Polyamidoamino Acids with Hydrophobic Side Chains Deriving from Natural α-Amino Acids. Polymers. 2018; 10(11):1261. https://doi.org/10.3390/polym10111261

Chicago/Turabian Style

Lazzari, Federica, Amedea Manfredi, Jenny Alongi, Raniero Mendichi, Fabio Ganazzoli, Giuseppina Raffaini, Paolo Ferruti, and Elisabetta Ranucci. 2018. "Self-Structuring in Water of Polyamidoamino Acids with Hydrophobic Side Chains Deriving from Natural α-Amino Acids" Polymers 10, no. 11: 1261. https://doi.org/10.3390/polym10111261

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