Self-Assembly and Crystal Structure of Boc-Protected Dipeptides Containing L-Phenylalanine and L-Tyrosine
Year: 2026
Type: article
Abstract: The self-assembly of a novel synthesized chiral dipeptide, Boc-p-nitro-L-phenylalanyl-tyrosine, into supramolecular structures is investigated by optical absorption and photoluminescence spectroscopy as well as single crystal X-ray diffraction. The compound is a diphenylalanine derivative belonging to a family of aromatic dipeptides that spontaneously self-organize into nanostructures through molecular recognition. The dipeptide exhibits several step-like peaks in its absorption band, indicative of self-assembly into quantum-confined nanostructures. In contrast, the parent Boc-p-nitro-L-phenylalanine amino acid lacks these features, indicating that the tyrosine residue favors quantum-confined self-assembly. Crystal structure determination reveals distinct packing styles: Boc-p-nitro-L-phenylalanine forms two-dimensional hydrogen-bonded layers, while the related p-nitro-free Boc-L-phenylalanyl-tyrosine dipeptide organizes into a 3D helical columnar architecture, driven by the additional hydrogen-bonding capacity of the peptide bond and tyrosine hydroxyl group, which favors the formation of a channel-type tetragonal architecture network over the planar sheets of the monomer. Furthermore, the introduction of a tyrosine residue into the Boc-p-nitro-L-phenylalanine molecule alters its supramolecular assembly, as the dipeptide Boc-p-nitro-L-phenylalanyl-tyrosine crystallizes as a monohydrate. The water molecule present in the structure acts as a bridge, participating in a hydrogen-bonding network between the tyrosine hydroxyl groups of neighboring columns through intermolecular interactions.
Source: Materials
DOI: 10.3390/ma19071319
Language: English
Subfield: Biomaterials
Field: Materials Science
Domain: Physical Sciences
Open Access status: gold
Estimated APC paid: $3,137
Awards: G1483381719, G1563530244, G1578237752, G1690109813, G2346795057, Laboratório Associado para a Química Verde - Tecnologias e Processos Limpos, Laboratório Associado para a Química Verde - Tecnologias e Processos Limpos, G336773693, G3391340659, Distorções estruturais controladas por campo eléctrico para dispositivos optoelectrónicos, G3692802076, G4577067103, G4971484151, G5624307780, G5868090805, G6219246445, G6875380692, G6997658380, Laboratório Associado para a Química Verde - Tecnologias e Processos Limpos, G7501588509, Biofunctional Cyclic Dipeptide Nanofibers for Energy Harvesting and Nonlinear Optical Conversion, G85722789, Fonónica não-linear: manipulando fases quânticas e multiferrocidade dinâmica, G8945308682
OpenAlex ID: W7140697059