Between Peptides and Bile Acids: Self-Assembly of Phenylalanine Substituted Cholic Acids

Biocompatible molecules that undergo self-assembly are of high importance in biological and medical applications of nanoscience. Peptides and bile acids are among the most investigated due to their ability to self-organize into many different, often stimuli-sensitive, supramolecular structures. With the aim of preparing molecules mixing the aggregation properties of bile acid and amino acid-based molecules, we report on the synthesis and self-association behavior of two diastereomers obtained by substituting a hydroxyl group of cholic acid with a L-phenylalanine residue. The obtained molecules are amphoteric, and we demonstrate that they show a pH-dependent self-assembly. Both molecules aggregate in globular micelles at high pH, whereas they form tubular superstructures under acid conditions. Unusual narrow nanotubes with outer and inner cross-section diameters of about 6 and 3 um are formed by the derivatives. The diasteroisomer with alpha orientation of the substituent forms in addition a wider tubule (17 nm cross-section diameter). The ability to pack in supramolecular tubules is explained in terms of a wedge-shaped bola-form structure of the derivatives. Parallel or antiparallel face-to-face dimers are hypothesized as fundamental building blocks for the formation of the narrow and wide nanotubes, respectively.

D'Annibale, Andrea (författare)
di Gregorio, Maria Chiara (författare)
Schillén, KarinLund University,Lunds universitet,Fysikalisk kemi,Enheten för fysikalisk och teoretisk kemi,Kemiska institutionen,Institutioner vid LTH,Lunds Tekniska Högskola,Physical Chemistry,Physical and theoretical chemistry,Department of Chemistry,Departments at LTH,Faculty of Engineering, LTH(Swepub:lu)fk1-ksc (författare)
Olsson, UlfLund University,Lunds universitet,Fysikalisk kemi,Enheten för fysikalisk och teoretisk kemi,Kemiska institutionen,Institutioner vid LTH,Lunds Tekniska Högskola,Physical Chemistry,Physical and theoretical chemistry,Department of Chemistry,Departments at LTH,Faculty of Engineering, LTH(Swepub:lu)fk1-uol (författare)
Sennato, Simona (författare)
Pavel, Nicolae V. (författare)
Galantini, Luciano (författare)
Fysikalisk kemiEnheten för fysikalisk och teoretisk kemi (creator_code:org_t)

Ingår i:The Journal of Physical Chemistry Part B: American Chemical Society (ACS)117:31, s. 9248-92571520-52071520-6106

Av författaren/redakt...: Travaglini, Lean ...; D'Annibale, Andr ...; di Gregorio, Mar ...; Schillén, Karin; Olsson, Ulf; Sennato, Simona; visa fler...; Pavel, Nicolae V ...; Galantini, Lucia ...; visa färre...

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