Great cyclodextrin chemistry by Konstantin Lebedinskii and Jindřich Jindřich preparing a series of 6-monohalo (Cl, Br, and I) β-cyclodextrin derivatives with various types of methylations. This new method opens the way for preparing poorly investigated monofunctionalized selectively methylated cyclodextrins.
Can ChatGPT pass Glycobiology?
Devin Ormsby Williams and Elisa Fadda we were interested in testing the boundaries of the LLM ChatGPT (www.openai.com) in areas of complex scientific writing tasks and exam-type questions in Carbohydrate Chemistry and Glycobiology. The results of this project allowed to gain insight on,
1) the strengths and limitations of the ChatGPT model to provide relevant and (most importantly) correct scientific information, and
2) the format(s) and complexity of the query required to obtain the desired output.
Ultimately, with the support of practical examples the aim is to inspire educators on how to successfully integrate ChatGPT in teaching, learning and assessment in higher education.
Today’s cyclodextrin:
At CarboHyde, we also deal with amphiphilic CDs; this application from this Canadian collaboration caught my attention.
Pseudo-face-to-face symmetry in the native CDs represents a distinctive advantage to designing amphiphilic materials capable of self-assembly into liquid crystals. In this work, a new family of amphiphilic β-CD derivatives possessing 14 stearoyl chains (non-polar) and 7 functionalized tetraethylene glycols were synthesized using an improved design and more efficient chemistry, and the synthetic targets showed excellent ability to form stable hexagonal columnar mesophases. Studies of a lithium composite revealed fast local Li-ion exchange processes with very low activation energies, suggesting the benefit of using these materials as potential electrolytes for high ionic conductions. The results from this work can guide the design of future generations of CD-based LC materials for ion conduction.
University of Calgary – Austin Che, Simon Trudel-Lachance, Jayar Espejo, Chang-Chun Ling
University of Alberta – Diganta Sarkar, Vladimir Michaelis
Simon Fraser University – Carson Zellman, Vance Williams
See the full article here: Functional group polarity-modulated formation of liquid crystals of amphiphilic cyclodextrins
Fascinating breaking application of cyclodextrin polymer proposed by Noemi Bognanni, Francesco Bellia and Graziella Vecchio from Università di Catania. Based on the features of cyclodextrins, they derivatized cross-linked cyclodextrin polymers with histidine or carcinine moieties and found that amylase enzymes do not hydrolyze cyclodextrin polymers. The new polymers can form copper(II) complexes and may act as nanochelators to counteract copper(II) dyshomeostasis-related diseases. Furthermore, the copper(II) complexes show superoxide dismutase activity, similar to free carcinine and histidine complexes. The antioxidant biological activity of the copper(II) complex formed in situ may protect cells from oxidative damage related to #copper dyshomeostasis.
Ribofuranose sugar conformation plays an important role in the structure and dynamics of functional nucleic acids such as siRNAs, AONs, aptamers, miRNAs, etc. Several chemical modifications have been introduced into sugar moiety to improve their therapeutic potential over the years. The stability of the oligonucleotide duplexes as well as the formation of stable and functional protein-oligonucleotide complexes are dictated by the conformation and dynamics of the sugar moiety. In this review, Gourav Das Harikrishna and Kiran Gore systematically categorize various ribofuranose sugar modifications employed in DNAs and RNAs so far. We discuss different stereoelectronic effects imparted by different substituents on the sugar ring and how these effects control sugar puckering. Using this data, it would be possible to predict the precise use of chemical modifications and design novel sugar-modified nucleosides for therapeutic oligonucleotides that can improve their physicochemical properties.
See the full article here: Influence of Sugar Modifications on the Nucleoside Conformation and Oligonucleotide Stability: A Critical Review
Interesting conceptual comparison of Conventional and Mechanochemical Syntheses of Cyclodextrin Derivatives by László Jicsinszky, Giancarlo Cravotto, et al. from the University of Turin.
See the full article in Molecules.
Have you always been fascinated by the creation and limitless use of rotaxanes like me? If so, this review is for you on their sequence-controlled synthesis.
National University of Singapore, Northwestern University – Han Han, James Seale, Liang Feng, Yunyan Qiu, Fraser Stoddart
From peptides to sugars: Design, Synthesis, and Characterization of Stapled Oligosaccharides. Oligosaccharide stapling increases enzymatic stability and cell penetration, opening new opportunities for using glycans in medicinal chemistry. – Max Planck Institute Manuel Garcia Ricardo, Emelie Ellen Reuber, Ling Yao, José Angel Danglad-Flores, Martina Delbianco, Peter Seeberger
Wonderful chemistry and insightful new possibilities.
Olivier Renaudet, David Goyard, Ángela Martín-Serrano Ortiz and Didier Boturynlick from Université Grenoble Alpes presents click chemistry to decorate synthetic multivalent scaffolds with glycans to mimic the cell surface glycocalyx and to develop applications in glycosciences.
Great reivew on glycoconjugates, their synthesis and pharmaceutical applications from Scripps Research (Sachin S. Shivatare, PhD, Vidya Shivatare and Chi-Huey Wong)
