Chiral and non-chiral assemblies from lipidated serine-based pseudopeptidic molecules

A series of lipidated molecules l-A1–l-A5 containing two serine units linked by a variety of aromatic spacers were designed and synthesized. Compound l-A1 containing a m -xylylene unit self-assembled into intertwined twisted-ribbons, while compound l-A2 containing a p -xylylene unit formed nano-size...

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Published inMolecular systems design & engineering Vol. 1; no. 2; pp. 163 - 168
Main Authors Bijesh, M. B., Dheepthi, N. U., Sapala, Appa Rao, Shandilya, Ashutosh, Khare, Kedar, Haridas, V.
Format Journal Article
LanguageEnglish
Published 01.01.2016
Subjects
Fibres
Formations
Mathematical analysis
Nanostructure
Ribbons
Self assembly
Spacers
Systems design
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Summary:A series of lipidated molecules l-A1–l-A5 containing two serine units linked by a variety of aromatic spacers were designed and synthesized. Compound l-A1 containing a m -xylylene unit self-assembled into intertwined twisted-ribbons, while compound l-A2 containing a p -xylylene unit formed nano-sized twisted-ribbons. A racemic mixture of l-A1 and d-A1 showed tapes, while a racemate from l-A2 and d-A2 showed fibres. In contrast, compounds l-A3 and l-A4 containing a benzene-1,3-dicarbonyl spacer showed a fibrillar morphology. Control over self-assembly was achieved by the choice of aromatic spacers and N-terminal substituents. The need for molecular curvature for the formation of twisted ribbons was demonstrated by the inability of control compound l-A5 to form twisted-ribbons.
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ISSN:2058-9689
2058-9689
DOI:10.1039/C6ME00009F