The existence of racemic compounds, comprised of pairs of opposite enantiomers as discrete molecular entities, has been accepted for over a century. However, their ability to remain as associated dimers when in solution is uncertain, if not generally doubted. In this article, data has been assembled to provide evidence for the presence of intact dimeric heterochiral assemblies in solution and presents DL-thalidomide as a probable example of this phenomenon.
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http://dx.doi.org/10.3109/00498254.2011.590547 | DOI Listing |
Nat Commun
December 2024
Institute of Physiological Chemistry, Faculty of Medicine, Philipps University of Marburg, Marburg, Germany.
Mirror-image proteins, composed of D-amino acids, are an attractive therapeutic modality, as they exhibit high metabolic stability and lack immunogenicity. Development of mirror-image binding proteins is achieved through chemical synthesis of D-target proteins, phage display library selection of L-binders and chemical synthesis of (mirror-image) D-binders that consequently bind the physiological L-targets. Monobodies are well-established synthetic (L-)binding proteins and their small size (~90 residues) and lack of endogenous cysteine residues make them particularly accessible to chemical synthesis.
View Article and Find Full Text PDFAngew Chem Int Ed Engl
December 2024
Institute of Molecular Functional Materials, State Key Laboratory of Synthetic Chemistry, and Department of Chemistry, The University of Hong Kong, Pokfulam Road, Hong Kong, 999077, P. R. China.
Chem Asian J
November 2024
State Key Laboratory of Supramolecular Structure and Materials, and Center for Supramolecular Chemical Biology, College of Chemistry, Jilin University, 2699 Qianjin Street, Changchun, 130012, China.
In this study, we focus on the designability and controllability of the interaction interface between secondary structures, and discover an important interface interaction between helical secondary structures by non-covalent synthesis along the helical axis. The formation of discrete heterochiral dimers consisting of left-handed helix and right-handed helix not only helps to discover nonclassical supramolecular chirality phenomena, but also enables controllable protein assembly. Highly ordered nanostructures were thus constructed using π-stacking dimerization of helical foldamers to control tetrameric avidin proteins.
View Article and Find Full Text PDFChem Sci
August 2024
Department of Organic Chemistry, Universidad Autónoma de Madrid Campus de Cantoblanco, C/Francisco Tomás y Valiente 7 28049 Madrid Spain
The columnar arrangement of bowl-shaped aromatics is a promising strategy for producing high-performing semiconductors. However, the structural factors that dictate the self-assembly of these molecules remain poorly understood. Herein, we show how chirality and peripheral substitution affect the columnar assembly of subphthalocyanines (SubPcs) in solution.
View Article and Find Full Text PDFChem Sci
August 2024
School of Applied and Interdisciplinary Sciences, Indian Association for the Cultivation of Science Kolkata 700032 India
Circularly polarized luminescence (CPL) is gaining interest across various disciplines, including materials science, pharmaceuticals, and sensing technologies. Organic molecules, due to their ease of synthesis and reduced toxicity, are a focus for achieving high dissymmetry values ( ) in CPL. Here, we present a low molecular weight molecule (1), a dipeptide (Ala-Phe) covalently linked with tetraphenyl-ethylene (TPE), an Aggregation-Induced Emission luminophore (AIE-gen).
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