Chemical Communications, Journal Year: 2022, Volume and Issue: 58(80), P. 11256 - 11259
Published: Jan. 1, 2022
Optimization of glycosylation conditions for automated glycan assembly is highly challenging, demands wasteful use precious building blocks, and relies on nontrivial analyses. We developed a semi-quantitative method optimization temperature that utilized minute quantities donors translated those to solid-phase assembly.
Language: Английский
Nature Synthesis, Journal Year: 2022, Volume and Issue: 1(11), P. 854 - 863
Published: Sept. 29, 2022
Language: Английский
Citations
83
JACS Au, Journal Year: 2023, Volume and Issue: 3(3), P. 628 - 656
Published: March 2, 2023
Glycosaminoglycans (GAGs) are complex polysaccharides exhibiting a vast structural diversity and fulfilling various functions mediated by thousands of interactions in the extracellular matrix, at cell surface, within cells where they have been detected nucleus. It is known that chemical groups attached to GAGs GAG conformations comprise "glycocodes" not yet fully deciphered. The molecular context also matters for structures functions, influence structure proteoglycan core proteins on sulfated vice versa warrants further investigation. lack dedicated bioinformatic tools mining data sets contributes partial characterization functional landscape GAGs. These pending issues will benefit from development new approaches reviewed here, namely (i) synthesis oligosaccharides build large diverse libraries, (ii) analysis sequencing mass spectrometry (e.g., ion mobility-mass spectrometry), gas-phase infrared spectroscopy, recognition tunnelling nanopores, modeling identify bioactive sequences, biophysical methods investigate binding interfaces, expand our knowledge understanding glycocodes governing recognition, (iii) artificial intelligence in-depth investigation GAGomic their integration with proteomics.
Language: Английский
Citations
63
Chemical Society Reviews, Journal Year: 2023, Volume and Issue: 52(22), P. 7773 - 7801
Published: Jan. 1, 2023
The structural complexity of glycans poses a serious challenge in the chemical synthesis glycosides, oligosaccharides and glycoconjugates. Glycan complexity, determined by composition, connectivity, configuration far exceeds what nature achieves with nucleic acids proteins. Consequently, glycoside ranks among most complex tasks organic synthesis, despite involving only simple type bond-forming reaction. Here, we introduce fundamental principles bond formation summarize recent advances oligosaccharide synthesis.
Language: Английский
Citations
45
Carbohydrate Polymers, Journal Year: 2024, Volume and Issue: 332, P. 121924 - 121924
Published: Feb. 9, 2024
Language: Английский
Citations
17
Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: unknown
Published: Jan. 1, 2024
Herein we utilise automated glycan assembly to complete solid-phase synthesis of defined heparan sulfate oligosaccharides, employing on resin O-sulfation and d -glucuronate disaccharide donors.
Language: Английский
Citations
9
Frontiers in Molecular Biosciences, Journal Year: 2022, Volume and Issue: 9
Published: June 14, 2022
Carbohydrates involving glycoconjugates play a pivotal role in many life processes. Better understanding toward glycobiological events including the structure–function relationship of these biomolecules and for diagnostic therapeutic purposes tailor-made vaccine development synthesis structurally well-defined oligosaccharides (OS) become important. Efficient chemical glycosylation high yield stereoselectivity is however challenging depends on fine tuning protection profile to get matching glycosyl donor–acceptor reactivity along with proper use other important external factors like catalyst, solvent, temperature, activator, additive. So far, methods have been reported several reviews also. In present review, we will concentrate our discussion recent trend α- β-selective reactions during past decade.
Language: Английский
Citations
33
Angewandte Chemie International Edition, Journal Year: 2022, Volume and Issue: 61(15)
Published: Jan. 15, 2022
Glycosidic bond formation is a continual challenge for practitioners. Aiming to enhance the reproducibility and efficiency of oligosaccharide synthesis, we studied relationship between glycosyl donor activation reaction temperature. A novel semi-automated assay revealed diverse responses members panel thioglycosides at various temperatures. The patterns protecting groups thiol aglycon combine cause remarkable differences in temperature sensitivity among building blocks. We introduce concept capture experimental insights, reasoning that glycosylations performed below this reference evade deleterious side reactions. Activation temperatures enable simplified treatment facilitate optimization usage. Isothermal glycosylation halved equivalents block required comparison standard "ramp" regime used solution- solid-phase synthesis to-date.
Language: Английский
Citations
31
Chemistry - A European Journal, Journal Year: 2024, Volume and Issue: 30(30)
Published: March 28, 2024
Abstract The chemical synthesis of complex oligosaccharides relies on efficient and highly reproducible glycosylation reactions. outcome a is contingent upon several environmental factors, such as temperature, acidity, the presence residual moisture, well steric, electronic, conformational aspects reactants. Each proceeds rapidly with high yield within rather narrow temperature range. For better control over glycosylations to ensure fast reliable reactions, systematic analysis 18 glycosyl donors revealed effect reagent concentration, water content, protecting groups, structure activation temperature. With these insights, we parametrize first step reaction be executed reliably efficiently.
Language: Английский
Citations
5
Journal of the American Chemical Society, Journal Year: 2024, Volume and Issue: 146(27), P. 18320 - 18330
Published: June 25, 2024
Fucoidan, a sulfated polysaccharide found in algae, plays central role marine carbon sequestration and exhibits wide array of bioactivities. However, the molecular diversity structural complexity fucoidan hinder precise structure–function studies. To address this, we present an automated method for generating well-defined linear branched α-fucan oligosaccharides. Our syntheses include oligosaccharides with up to 20 cis-glycosidic linkages, diverse branching patterns, 11 sulfate monoesters. In this study, demonstrate utility these by (i) characterizing two endo-acting glycoside hydrolases (GH107), (ii) utilizing them as standards NMR studies confirm suggested structures algal fucoidans, (iii) developing microarray. This microarray enabled screening specificity four monoclonal antibodies (mAb) targeting fucoidan. It was that mAb BAM4 has cross-reactivity β-glucans, while BAM2 reactivity fucoidans 4-O-sulfate esters. Knowledge epitope provided evidence globally abundant diatom, Thalassiosira weissflogii, synthesizes homology those brown algae. Automated glycan assembly provides access These provide basis level investigations into fucoidan's roles medicine sequestration.
Language: Английский
Citations
5
Device, Journal Year: 2024, Volume and Issue: 2(10), P. 100499 - 100499
Published: Aug. 7, 2024
Fast, affordable, and reliable access to complex glycans is essential meet the demand for custom-made research tools glycosciences. Automated glycan assembly (AGA), based on solid-phase synthesis paradigm allows quickly producing a range of biologically relevant oligosaccharides. The instrument sets limits as types chemistries that can be executed. new, smaller, more economical device quick temperature adjustments between −40°C +90°C an energy-efficient local-temperature-controlled (LTC) reactor. power new illustrated in context several AGA syntheses
Language: Английский
Citations
4