Modular Synthesis of a Tridecasaccharide Motif of Bacteroides vulgatus Lipopolysaccharides against Inflammatory Bowel Diseases through an Orthogonal One‐Pot Glycosylation Strategy DOI

Yunqin Zhang,

Leilei Wang,

Qingli Zhou

et al.

Angewandte Chemie International Edition, Journal Year: 2023, Volume and Issue: 62(22)

Published: March 3, 2023

Lipopolysaccharides from Bacteroides vulgatus represent interesting targets for the treatment of inflammatory bowel diseases. However, efficient access to long, branched and complex lipopolysaccharides remains challenging. Herein, we report modular synthesis a tridecasaccharide vulgates through an orthogonal one-pot glycosylation strategy based on glycosyl ortho-(1-phenylvinyl)benzoates, which avoids issues thioglycoside-based synthesis. Our approach also features: 1) 5,7-O-di-tert-butylsilylene-directed stereoselective construction α-Kdo linkage; 2) hydrogen-bond-mediated aglycone delivery formation β-mannosidic bonds; 3) remote anchimeric assistance assembly α-fucosyl 4) several synthetic steps strategic use protecting groups streamline oligosaccharide assembly; 5) convergent [1+6+6] target.

Language: Английский

Solid-State NMR Investigations of Extracellular Matrixes and Cell Walls of Algae, Bacteria, Fungi, and Plants DOI Creative Commons
Nader Ghassemi, Alexandre Poulhazan, Fabien Deligey

et al.

Chemical Reviews, Journal Year: 2021, Volume and Issue: 122(10), P. 10036 - 10086

Published: Dec. 8, 2021

Extracellular matrixes (ECMs), such as the cell walls and biofilms, are important for supporting integrity function regulating intercellular communication. These biomaterials also of significant interest to production biofuels development antimicrobial treatment. Solid-state nuclear magnetic resonance (ssNMR) magic-angle spinning-dynamic polarization (MAS-DNP) uniquely powerful understanding conformational structure, dynamical characteristics, supramolecular assemblies carbohydrates other biomolecules in ECMs. This review highlights recent high-resolution investigations intact ECMs native cells many organisms spanning across plants, bacteria, fungi, algae. We spotlight structural principles identified ECMs, discuss current technical limitation underexplored biochemical topics, point out promising opportunities enabled by advances rapidly evolving ssNMR technology.

Language: Английский

Citations

114

Liquid-state NMR spectroscopy for complex carbohydrate structural analysis: A hitchhiker's guide DOI Creative Commons
Immacolata Speciale, Anna Notaro, Pilar García-Vello

et al.

Carbohydrate Polymers, Journal Year: 2021, Volume and Issue: 277, P. 118885 - 118885

Published: Nov. 13, 2021

Structural determination of carbohydrates is mostly performed by liquid-state NMR, and it a demanding task because the NMR signals these biomolecules explore rather narrow range chemical shifts, with result that resonances each monosaccharide unit heavily overlap those others, thus muddling their punctual identification. However, full attribution shifts brings great advantages: discloses nature constituents, way they are interconnected, in some cases absolute configuration, paves to other more sophisticated analyses. The purpose this review provide practical guide into challenging subject. It will drive through strategy used assign data, pinpointing core information disclosed from experiment, suggesting useful tricks for interpretation, along resources pivotal during study biomolecules.

Language: Английский

Citations

109

Primary Structure of Glycans by NMR Spectroscopy DOI Creative Commons
Carolina Fontana, Göran Widmalm

Chemical Reviews, Journal Year: 2023, Volume and Issue: 123(3), P. 1040 - 1102

Published: Jan. 9, 2023

Glycans, carbohydrate molecules in the realm of biology, are present as biomedically important glycoconjugates and a characteristic aspect is that their structures many instances branched. In determining primary structure glycan, sugar components including absolute configuration ring form, anomeric configuration, linkage(s), sequence, substituents should be elucidated. Solution state NMR spectroscopy offers unique opportunity to resolve all these aspects at atomic resolution. During last two decades, advancement both experiments spectrometer hardware have made it possible unravel more efficiently. These developments applicable glycans include, inter alia, reduce spectral overlap, use selective excitations, record tilted projections multidimensional spectra, acquire spectra by multiple receivers, utilize polarization fast-pulsing techniques, concatenate pulse-sequence modules several single measurement, pure shift correlated devoid scalar couplings, employ stable isotope labeling efficiently obtain homo- and/or heteronuclear correlations, well those rely on dipolar cross-correlated interactions for sequential information. Refined computer programs spin simulation chemical prediction aid structural elucidation glycans, which notorious limited dispersion. Hardware include cryogenically cold probes dynamic nuclear resulting enhanced sensitivity ultrahigh field spectrometers with 1H resonance frequency higher than 1 GHz, thus improving resolution resonances. Taken together, will future make elucidate great detail, thereby forming basis understanding how interact other molecules.

Language: Английский

Citations

62

A Novel L-Cys@Cu MOF Embedding onto Cotton Fiber Surfaces to Exert Excellent Antiviral and Antibacterial Effects DOI

Yuanxiang Xiao,

Jingjing Jiang, Rui Cai

et al.

Advanced Fiber Materials, Journal Year: 2024, Volume and Issue: 6(2), P. 444 - 457

Published: Feb. 6, 2024

Language: Английский

Citations

21

Multifaceted Computational Modeling in Glycoscience DOI
Serge Pérez, Olga Makshakova

Chemical Reviews, Journal Year: 2022, Volume and Issue: 122(20), P. 15914 - 15970

Published: July 5, 2022

Glycoscience assembles all the scientific disciplines involved in studying various molecules and macromolecules containing carbohydrates complex glycans. Such an ensemble involves one of most extensive sets quantity occurrence since they occur microorganisms higher organisms. Once compositions sequences these are established, determination their three-dimensional structural dynamical features is a step toward understanding molecular basis underlying properties functions. The range relevant computational methods capable addressing such issues anchored by specificity stereoelectronic effects from quantum chemistry to mesoscale modeling throughout dynamics mechanics coarse-grained docking calculations. Review leads reader through detailed presentations applications modeling. illustrations cover carbohydrate–carbohydrate interactions, glycolipids, N- O-linked glycans, emphasizing role SARS-CoV-2. presentation continues with structure polysaccharides solution solid-state lipopolysaccharides membranes. full protein-carbohydrate interactions presented, as exemplified carbohydrate-active enzymes, transporters, lectins, antibodies, glycosaminoglycan binding proteins. A final section list 150 tools databases help address many glycobioinformatics.

Language: Английский

Citations

53

Lipopolysaccharides at Solid and Liquid Interfaces: Models for Biophysical Studies of the Gram-negative Bacterial Outer Membrane DOI Creative Commons
Nicolò Paracini, Emanuel Schneck, Anne Imberty

et al.

Advances in Colloid and Interface Science, Journal Year: 2022, Volume and Issue: 301, P. 102603 - 102603

Published: Jan. 23, 2022

Lipopolysaccharides (LPSs) are a constitutive element of the cell envelope Gram-negative bacteria, representing main lipid in external leaflet their outer membrane (OM) bilayer. These unique surface-exposed glycolipids play central role interactions organisms with surrounding environment and represent key for protection against antimicrobials development antibiotic resistance. The biophysical investigation wide range different types vitro model membranes containing reconstituted LPS has revealed functional structural properties these peculiar lipids, providing molecular-level details interaction antimicrobial compounds. assemblies at interfaces versatile tool to study OM by exploiting several surface-sensitive techniques, particular X-ray neutron scattering, which can probe structure thin films sub-nanometer resolution. This review provides an overview approaches employed investigate LPS, focusing on studies Langmuir monolayers air/liquid interface supported LPS-containing solid/liquid interfaces.

Language: Английский

Citations

50

Interdisciplinary‐Inspired Smart Antibacterial Materials and Their Biomedical Applications DOI Open Access
Yuzheng Wu, Pei Liu, Babak Mehrjou

et al.

Advanced Materials, Journal Year: 2023, Volume and Issue: 36(17)

Published: July 20, 2023

Abstract The discovery of antibiotics has saved millions lives, but the emergence antibiotic‐resistant bacteria become another problem in modern medicine. To avoid or reduce overuse antibacterial treatments, stimuli‐responsive materials, pathogen‐targeting nanoparticles, immunogenic nano‐toxoids, and biomimetic materials are being developed to make sterilization better smarter than conventional therapies. common goal smart (SAMs) is increase antibiotic efficacy function via an mechanism different from that order biological properties while reducing risk drug resistance. research development SAMs increasingly interdisciplinary because new designs require knowledge fields input/collaboration scientists fields. A good understanding energy conversion physiological characteristics cells bacteria, bactericidal structures components nature expected promote SAMs. In this review, importance multidisciplinary insights for emphasized, latest advances categorized discussed according pertinent disciplines including science, physiology, biomimicry.

Language: Английский

Citations

39

Nanosilver: An Old Antibacterial Agent with Great Promise in the Fight against Antibiotic Resistance DOI Creative Commons

Kyra G. Kaiser,

Victoire Delattre,

Victoria Frost

et al.

Antibiotics, Journal Year: 2023, Volume and Issue: 12(8), P. 1264 - 1264

Published: July 31, 2023

Antibiotic resistance in bacteria is a major problem worldwide that costs 55 billion USD annually for extended hospitalization, resource utilization, and additional treatment expenditures the United States. This review examines roles forms of silver (e.g., bulk Ag, salts (AgNO

Language: Английский

Citations

37

Site-Selective C–O Bond Editing of Unprotected Saccharides DOI
Guanjie Wang,

Chang Chin Ho,

Zhixu Zhou

et al.

Journal of the American Chemical Society, Journal Year: 2023, Volume and Issue: 146(1), P. 824 - 832

Published: Dec. 20, 2023

Glucose and its polyhydroxy saccharide analogs are complex molecules that serve as essential structural components in biomacromolecules, natural products, medicines, agrochemicals. Within the expansive realm of saccharides, a significant area research revolves around chemically transforming naturally abundant units to intricate or uncommon such oligosaccharides rare sugars. However, partly due presence multiple hydroxyl groups with similar reactivities complexities arising from stereochemistry, transformation unprotected sugars desired target remains challenging. One formidable challenge lies efficient selective activation modification C–O bonds saccharides. In this study, we disclose modular 2-fold "tagging–editing" strategy allows for direct editing enabling rapid preparation valuable drug derivatives. The first step, referred "tagging", involves catalytic site-selective installation photoredox active carboxylic ester group specific unit an sugar. second namely, "editing", features bond cleavage form carbon radical intermediate undergoes further transformations C–H C–C formations. Our constitutes most effective shortest route medicines other bearing

Language: Английский

Citations

27

Antimicrobial Peptide Coating of TiO2 Nanoparticles for Boosted Antimicrobial Effects DOI Creative Commons
Lucrezia Caselli, Tanja Traini, Samantha Micciulla

et al.

Advanced Functional Materials, Journal Year: 2024, Volume and Issue: unknown

Published: June 20, 2024

Abstract This study explores the coating of photocatalytic nanoparticles with antimicrobial peptides (AMPs) for boosted effects, and how such effects depend on AMP properties. For this, TiO 2 are coated KYE21 or its hydrophobically enhanced variant WWWKYE21. Mirroring free peptides, displayed higher binding UV‐induced degradation bacteria‐like than mammalian‐like membranes. In addition, they degraded bacterial lipopolysaccharides (LPS). WWWKYE21‐coated to LPS membranes degradation, although saturation found at high nanoparticle binding. Neutron reflectometry showed that peptide‐coated resulted in partial lipid removal absence UV, but UV illumination caused additional featuring increases hydration headgroup acyl chain regions. LPS, induced outer O‐antigen region. Analogous findings model systems, against Escherichia coli bacteria pronounced, while toxicity human monocytes remained low. Altogether, results show boosts without causing cell toxicity. From a broader perspective, points potential nanoarchitectonic combination component properties design composite NP

Language: Английский

Citations

13