The 2022 Nobel Prize in Chemistry—sweet! DOI Open Access
Michael Boyce, Stacy A. Malaker, Nicholas M. Riley

et al.

Glycobiology, Journal Year: 2023, Volume and Issue: 33(3), P. 178 - 181

Published: March 1, 2023

On 2022 October 5, The Royal Swedish Academy of Sciences announced its decision to award the Nobel Prize in Chemistry Carolyn R. Bertozzi (Stanford University), Morten Meldal (University Copenhagen), and K. Barry Sharpless (Scripps Research) “for development click chemistry bioorthogonal chemistry.” glycobiology community was exultant! To understand why, one must appreciate how challenges glycoscience research motivated these transformative chemical tools. Glycoscience has a storied history contributing significant discoveries hematology, metabolism, microbiology, other fields biomedical throughout much 20th century. But when 1970s 80s ushered new molecular biology methods that accelerated studies nucleic acid protein function, glycans began lag behind (National Research Council 2012; Agre et al. 2016). Fortunately, since then, vast improvements have been made areas such as carbohydrate synthesis glycan arrays (Rillahan Paulson 2011; Li Bennett 2022), availability glyco-enzymes small molecule inhibitors (Moremen 2018; Almahayni mass spectrometry analysis glycopeptides (Ruhaak Suttapitugsakul 2020; Bagdonaite well understanding biological systems (Varki 2017), all which facilitated function. Notwithstanding important advances, detection presented recurrent challenge. Indeed, modern practice hinges on ability specifically address biomolecule interest so it can be isolated, visualized, or quantified. For acids, this often achieved via hybridization, whereas specific proteins detected tracked using antibodies tagging methods. genetically encoded tags cannot used track glycans, are not primary gene products. glycobiologist, lectins essential tools but suffer from limitations relating specificity affinity (Cummings 2022).

Language: Английский

From structure to function – Ligand recognition by myeloid C-type lectin receptors DOI Creative Commons

Swantje Fischer,

Felix Stegmann,

Vinayaga S. Gnanapragassam

et al.

Computational and Structural Biotechnology Journal, Journal Year: 2022, Volume and Issue: 20, P. 5790 - 5812

Published: Jan. 1, 2022

• Structural characteristics of myeloid C-type lectin receptors and their ligands.

Language: Английский

Citations

38
Efficient and versatile formation of glycosidic bonds via catalytic strain-release glycosylation with glycosyl ortho−2,2-dimethoxycarbonylcyclopropylbenzoate donors DOI Creative Commons
Han Ding, Jian Lyu,

Xiao-Lin Zhang

et al.

Nature Communications, Journal Year: 2023, Volume and Issue: 14(1)

Published: July 7, 2023

Catalytic glycosylation is a vital transformation in synthetic carbohydrate chemistry due to its ability expediate the large-scale oligosaccharide synthesis for glycobiology studies with consumption of minimal amounts promoters. Herein we introduce facile and efficient catalytic employing glycosyl ortho-2,2-dimethoxycarbonylcyclopropylbenzoates (CCBz) promoted by readily accessible non-toxic Sc(III) catalyst system. The reaction involves novel activation mode esters driven ring-strain release an intramolecularly incorporated donor-acceptor cyclopropane (DAC). versatile CCBz donor enables highly construction O-, S-, N-glycosidic bonds under mild conditions, as exemplified convenient preparation synthetically challenging chitooligosaccharide derivatives. Of note, gram-scale tetrasaccharide corresponding Lipid IV modifiable handles achieved using strain-release glycosylation. These attractive features promise this be prototype developing next generation

Language: Английский

Citations

22
Chemical biology tools to probe bacterial glycans DOI Creative Commons

Daniel Calles-Garcia,

Danielle H. Dube

Current Opinion in Chemical Biology, Journal Year: 2024, Volume and Issue: 80, P. 102453 - 102453

Published: April 5, 2024

Bacterial cells are covered by a complex carbohydrate coat of armor that allows bacteria to thrive in range environments. As testament the importance bacterial glycans, effective and heavily utilized antibiotics including penicillin vancomycin target disrupt glycocalyx. Despite their importance, study glycans lags far behind eukaryotic counterparts. use large palette monosaccharides craft leading molecules significantly more than refractory study. Fortunately, chemical tools designed probe have yielded insights into these molecules, structures, biosynthesis, functions.

Language: Английский

Citations

4
HPLC‐Based Automated Synthesis and Purification of Carbohydrates DOI
Gustavo A. Kashiwagi, Laura Petrosilli, Samira Escopy

et al.

Chemistry - A European Journal, Journal Year: 2024, Volume and Issue: 30(43)

Published: April 30, 2024

Reported herein is a new HPLC-based automated synthesizer (HPLC-A) capable of temperature-controlled synthesis and purification carbohydrates. The developed platform allows to perform various protecting group manipulations as well the O- N-glycosides. A fully was showcased in application different carbohydrate derivatives including glycosides, oligosaccharides, glycopeptides, glycolipids, nucleosides.

Language: Английский

Citations

4
Recent advances in chemical synthesis of O-linked glycopeptides and glycoproteins: An advanced synthetic tool for exploring the biological realm DOI
Jie Zhao,

Farong Ye,

Ping Huang

et al.

Current Opinion in Chemical Biology, Journal Year: 2023, Volume and Issue: 77, P. 102405 - 102405

Published: Oct. 26, 2023

Language: Английский

Citations

10
Stereoelectronic Effect of Protecting Groups on the Stability of Galactosyl Donor Intermediates DOI Creative Commons
R. W. M. Kwok,

Ryan Rutkoski,

Pavel Nagorny

et al.

Molecules, Journal Year: 2025, Volume and Issue: 30(2), P. 218 - 218

Published: Jan. 7, 2025

Using methods of DFT, we investigated the effect electron withdrawing and donating groups on relative stability tentative glycosyl donor reaction intermediates. The calculation shows that by changing stereoelectronic properties protecting group, can influence dioxolenium type intermediates up to 10 kcal mol−1, increasing nucleophillicity 4-O-Bz intermediate becomes more stable than a triflate–donor pair. We exploited this mechanism design galactosyl donors with custom O2 O4, outcome cyclohexanol. showed no change in product distribution, which suggests neighboring group participation takes precedence over remote due kinetic barriers.

Language: Английский

Citations

0
The importance of glycotriazoles in medicinal chemistry – A narrative review DOI
Rayssa de Cassia Alves Iemini, Dalila Junqueira Alvarenga,

Ana Laura Marques Trinca

et al.

Journal of Carbohydrate Chemistry, Journal Year: 2025, Volume and Issue: unknown, P. 1 - 27

Published: April 11, 2025

Language: Английский

Citations

0
Enhanced Experimental Set-Up for HPLC-Based Automated Synthesis and Purification of Carbohydrate Building Blocks DOI
Gustavo A. Kashiwagi, Alexei V. Demchenko

Carbohydrate Research, Journal Year: 2025, Volume and Issue: unknown, P. 109554 - 109554

Published: May 1, 2025

Language: Английский

Citations

0
The 2022 Nobel Prize in Chemistry—sweet! DOI Open Access
Michael Boyce, Stacy A. Malaker, Nicholas M. Riley

et al.

Glycobiology, Journal Year: 2023, Volume and Issue: 33(3), P. 178 - 181

Published: March 1, 2023

On 2022 October 5, The Royal Swedish Academy of Sciences announced its decision to award the Nobel Prize in Chemistry Carolyn R. Bertozzi (Stanford University), Morten Meldal (University Copenhagen), and K. Barry Sharpless (Scripps Research) “for development click chemistry bioorthogonal chemistry.” glycobiology community was exultant! To understand why, one must appreciate how challenges glycoscience research motivated these transformative chemical tools. Glycoscience has a storied history contributing significant discoveries hematology, metabolism, microbiology, other fields biomedical throughout much 20th century. But when 1970s 80s ushered new molecular biology methods that accelerated studies nucleic acid protein function, glycans began lag behind (National Research Council 2012; Agre et al. 2016). Fortunately, since then, vast improvements have been made areas such as carbohydrate synthesis glycan arrays (Rillahan Paulson 2011; Li Bennett 2022), availability glyco-enzymes small molecule inhibitors (Moremen 2018; Almahayni mass spectrometry analysis glycopeptides (Ruhaak Suttapitugsakul 2020; Bagdonaite well understanding biological systems (Varki 2017), all which facilitated function. Notwithstanding important advances, detection presented recurrent challenge. Indeed, modern practice hinges on ability specifically address biomolecule interest so it can be isolated, visualized, or quantified. For acids, this often achieved via hybridization, whereas specific proteins detected tracked using antibodies tagging methods. genetically encoded tags cannot used track glycans, are not primary gene products. glycobiologist, lectins essential tools but suffer from limitations relating specificity affinity (Cummings 2022).

Language: Английский

Citations

4