Nucleobase morpholino β amino acids as molecular chimeras for the preparation of photoluminescent materials from ribonucleosides

Abstract

Bioinspired smart materials represent a tremendously growing research field and the obtainment of new building blocks is at the molecular basis of this technology progress. In this work, colloidal materials have been prepared in few steps starting from ribonucleosides. Nucleobase morpholino β-amino acids are the chimera key intermediates allowing Phe–Phe dipeptides’ functionalization with adenine and thymine. The obtained compounds self-aggregate showing enhanced photoluminescent features, such as deep blue fluorescence and phosphorescence emissions.

Stimulus-responsive liposomes for biomedical applications

“…All of them are produced using "bottom-up" approaches, taking advantage of self-assembly (SA). SA can be defined as an "autonomous organization of components into ordered pattern or structures", and represents an elegant approach to fabricating nanostructures [13][14][15]. During SA, non-covalent interactions take part in defining the final features of the obtained nanomaterial.…”

Fishing in the Toolbox of Cyclic Turn Mimics: a Literature Overview of the Last Decade

“…However, the burgeoning growth of peptide-based nanomaterials could be the next important application of peptidomimetics. [72,73] The possibility to fish in the already available toolbox of turn mimics could thus open new frontiers and perspectives in the development of bio-inspired compounds with smart applications.…”

From Prebiotic Chemistry to Supramolecular Biomedical Materials: Exploring the Properties of Self-Assembling Nucleobase-Containing Peptides

“…In this regard, studies on non-enzymatic replication-a central mechanism driving chemical evolution-focused recently on nucleopeptides using chimeric nucleobase-peptide derivatives (1 and 2, named RAA and RTT, respectively, Figure 3). It was proven that different mechanisms control the replication of complementary In addition to targeting complementary DNA and RNA sequences, nucleopeptides are endowed with further biomedically relevant properties, as they are able to self-assemble forming supramolecular networks [39,40], they can cross cellular membranes [41,42] and exert other important functions, such as the delivery of small molecules and oligonucleotidebased drugs [43][44][45][46].…”

“…Short nucleopeptides such as nucleobase-containing diserine, diphenylalanine, and dityrosine were also proven to form self-assemblies characterized by circular dichroism spectroscopy and light scattering [15,117]. Nucleopeptide-based colloidal materials were prepared using nucleobase morpholino β-amino acids [40]. These were used as intermediates, together with phenylalanine residues, to form diphenylalanine peptides functionalized with adenine and thymine bases.…”