Article
Chemistry, Multidisciplinary
Mareike A. Rapp, Oliver R. Baudendistel, Ulrich E. Steiner, Valentin Wittmann
Summary: Research shows that the reaction rate of oxyamine ligation can be significantly accelerated when glycosyl amines are used as starting materials, making the method more efficient. This approach is particularly useful for the analysis of acid-sensitive oligosaccharides.
Article
Chemistry, Multidisciplinary
Wei-Wei Shi, Chaowei Shi, Tong-Yue Wang, Yu-Lei Li, Yong-Kang Zhou, Xu-Han Zhang, Donald Bierer, Ji-Shen Zheng, Lei Liu
Summary: The chemical synthesis of correctly folded proteins with multiple or interchain disulfide bonds was expedited using a removable glycosylation modification (RGM) strategy, which introduces O-linked beta-N-acetylglucosamine (O-GlcNAc) groups to improve folding and can be efficiently removed afterwards.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2022)
Article
Polymer Science
Marie Rosselin, Zoeisha S. Chinoy, Lourdes Monica Bravo-Anaya, Sebastien Lecommandoux, Elisabeth Garanger
Summary: The study showed that the presence of a linker at the anomeric position of galactose and the absence of positive charge on the polypeptide residue holding the sugar unit were critical for binding to RCA120 in the synthetic elastin-like glycopolypeptides library.
Article
Chemistry, Analytical
Juhi Samal, Tana V. Palomino, Judy Chen, David C. Muddiman, Tatiana Segura
Summary: N-linked glycosylation is a complex protein modification that plays a role in cellular signaling and metabolism. Aberrant protein glycosylation is a characteristic feature of many diseases. Spatial profiling of N-glycans through imaging on tissue sections can be used for disease diagnosis. Infrared matrix-assisted laser desorption electrospray ionization (IR-MALDESI) is a sensitive technique that can be used for mass spectrometry imaging.
ANALYTICAL CHEMISTRY
(2023)
Article
Biochemistry & Molecular Biology
Sunaina Kiran Prabhu, Chao Li, Guanghui Zong, Roushu Zhang, Lai-Xi Wang
Summary: Core fucosylation plays a crucial role in modulating the structure and biological functions of glycoproteins, but only a few alpha-L-fucosidases are capable of removing core fucose from intact glycoproteins. This study found that bacterial alpha-L-fucosidases from Lactobacillus casei and Bacteroides fragilis could only hydrolyze truncated Fuc alpha 1,6GlcNAc-peptide substrates, while the human alpha-L-fucosidase showed activity in removing core fucose from intact glycopeptides and glycoproteins. Additionally, the human alpha-L-fucosidase was the only enzyme that exhibited some capability to remove core fucose from intact IgG antibodies.
BIOORGANIC & MEDICINAL CHEMISTRY
(2021)
Article
Biotechnology & Applied Microbiology
Apichaya Bunyatratchata, Annabelle Le Parc, Juliana Maria Leite Nobrega de Moura Bell, Josh L. Cohen, Hatice Duman, Aysenur Arslan, Merve Kaplan, Daniela Barile, Sercan Karav
Summary: Milk glycoproteins have various biological roles, including antibacterial and antiviral activities, as well as modulating immune responses. The released N-glycans from milk glycoproteins are important for the growth of bifidobacteria in infants. However, the mechanisms and contributions of glycans to the biological activities of glycoproteins are still not fully understood.
ENZYME AND MICROBIAL TECHNOLOGY
(2023)
Article
Biochemistry & Molecular Biology
Mojgan Atashi, Cristian D. Gutierrez Reyes, Vishal Sandilya, Waziha Purba, Parisa Ahmadi, Md. Abdul Hakim, Firas Kobeissy, Giuseppe Plazzi, Monica Moresco, Bartolo Lanuzza, Raffaele Ferri, Yehia Mechref, Mauro Fasano
Summary: This study investigates the glycoproteins in narcolepsy type 1 (NT1) disease and identifies unique N-glycopeptides that show significant changes between NT1 patients and healthy individuals. These glycopeptides may play a role in the pathophysiology of NT1.
Article
Chemistry, Multidisciplinary
Lifeng Sun, Pradeep Chopra, Geert-Jan Boons
Summary: A new method for the synthesis of heparan sulfate oligosaccharides composed of unsulfonated fragments of different lengths was reported. Competition binding studies showed that the length of the unsulfonated fragment modulates the binding of chemokines.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Oncology
Jun Li, Ting Zhao, Jing Li, Jiechen Shen, Li Jia, Bojing Zhu, Liuyi Dang, Chen Ma, Didi Liu, Fan Mu, Liangshuo Hu, Shisheng Sun
Summary: This study identified numerous unique N-glycan structures in ICC through precision N-glycoproteomic analysis, providing a valuable resource for future research on ICC diagnostic biomarkers, therapeutic targets, and mechanism investigations.
MOLECULAR ONCOLOGY
(2022)
Article
Chemistry, Multidisciplinary
Yashapal Singh, Samira Escopy, Melanie Shadrick, Mithila D. Bandara, Keith J. Stine, Alexei V. Demchenko
Summary: Human milk oligosaccharides (HMO) are an active area of research in glycoscience and nutrition due to their involvement in infant development and potential disease prevention. This study reports the chemical synthesis of two core hexasaccharides found in human milk, pLNH and pLNnH, using a 3+3 convergent coupling strategy.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Agricultural Engineering
Elena M. Rojo, Irene Piedra, Alicia M. Gonzalez, Marisol Vega, Silvia Bolado
Summary: The study compared the effects of different enzymes on the solubilization and recovery of components from microalgae-bacteria grown in piggery wastewater and microalgae grown in synthetic media by enzymatic hydrolysis. Results showed higher carbohydrate solubilizations from microalgae-bacteria compared to pure microalgae, and Proteases solubilized xylose remarkably well. Alcalase hydrolysis provided the highest peptide recovery, while Protamex resulted in low peptide recoveries but larger peptide sizes.
BIORESOURCE TECHNOLOGY
(2021)
Article
Biochemical Research Methods
H. Mehmet Kayili, Bekir Salih
Summary: This study utilized high-throughput glyco-analytical strategies to analyze the N-glycosylation sites and glycan contents of human thyroglobulin. The results revealed the presence of high-mannose type glycans at some sites and complex/hybrid type glycans at other regions, with sulfated glycoform structures detected at sites containing complex/hybrid type glycans.
JOURNAL OF PROTEOMICS
(2022)
Article
Chemistry, Multidisciplinary
Gael M. Vos, Yunfei Wu, Roosmarijn van der Woude, Robert P. de Vries, Geert-Jan Boons
Summary: This paper introduces a chemo-enzymatic strategy for synthesizing poly-N-acetyl lactosamines (polyLacNAc) in a regioselective manner. The strategy involves enzymatic assembly of oligo-LacNAc chains and modification at specific positions using traceless blocking groups. The methodology allows for the synthesis of polyLacNAc chains with various topologies.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Chemistry, Multidisciplinary
Tianlu Li, Youqin Zhang, Tong Li, Haoru Zhuang, Fengshan Wang, Ning Wang, Richard R. Schmidt, Peng Peng
Summary: O-Mannosylation is crucial for various biological processes, but its precise function is still largely unknown. This study developed a chemoenzymatic strategy to assemble diverse O-mannosyl alpha-dystroglycan (alpha-DG) glycopeptides efficiently, demonstrating its effectiveness and flexibility.
CHINESE JOURNAL OF CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Hendrik Hessefort, Angelina Gross, Simone Seeleithner, Markus Hessefort, Tanja Kirsch, Lukas Perkams, Klaus Ole Bundgaard, Karen Gottwald, David Rau, Christopher Guenther Franz Graf, Elisabeth Rozanski, Sascha Weidler, Carlo Unverzagt
Summary: The in-vivo activity of EPO is carbohydrate-dependent, with the number of sialic acid residues regulating its circulatory half-life. A chemoenzymatic approach was developed for obtaining glycoforms of EPO with and without sialic acids. Synthetic EPOs showed biological recognition by forming 1:1 complexes with recombinant EPO receptor.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Editorial Material
Chemistry, Multidisciplinary
Antony J. Fairbanks
Article
Biochemistry & Molecular Biology
Sivasinthujah Paramasivam, Antony J. Fairbanks
CARBOHYDRATE RESEARCH
(2019)
Review
Biochemistry & Molecular Biology
Antony J. Fairbanks
CURRENT OPINION IN CHEMICAL BIOLOGY
(2019)
Article
Chemistry, Organic
Xin Qiu, Antony J. Fairbanks
Article
Chemistry, Organic
Xiaoyi Wang, Anneliese S. Ashhurst, Luke J. Dowman, Emma E. Watson, Henry Y. Li, Antony J. Fairbanks, Mark Larance, Ann Kwan, Richard J. Payne
Article
Biochemistry & Molecular Biology
Antony J. Fairbanks
Summary: 2-Chloro-1,3-dimethylimidazolinium chloride (DMC) and its derivatives are valuable for selectively activating the anomeric center of unprotected reducing sugars in aqueous solution, allowing for efficient synthesis of glycosides and glycoconjugates without traditional protecting group manipulations. This mini-review explores the development and recent applications of DMC in protecting group-free synthesis.
CARBOHYDRATE RESEARCH
(2021)
Article
Biochemistry & Molecular Biology
Moritz Lasse, Anja R. Stampfli, Thomas Orban, Roshit K. Bothara, Juliet A. Gerrard, Antony J. Fairbanks, Neil R. Pattinson, Renwick C. J. Dobson
Summary: The study identified acrolein modifications on hemoglobin using mass spectrometry and found that these modifications have minimal impact on the secondary structure of hemoglobin. Acrolein modifications promote the formation of crosslinked octamers and alter the response to O2 binding. The study provides qualitative evidence for potential targeted mass spectrometric or immunometric assays for acrolein modified hemoglobin as an oxidative stress marker.
BIOCHIMICA ET BIOPHYSICA ACTA-GENERAL SUBJECTS
(2021)
Article
Biochemistry & Molecular Biology
Michael J. Currie, Lavanyaa Manjunath, Christopher R. Horne, Phillip M. Rendle, Ramaswamy Subramanian, Rosmarie Friemann, Antony J. Fairbanks, Andrew C. Muscroft-Taylor, Rachel A. North, Renwick C. J. Dobson
Summary: The study found that the enzyme NanE may use a novel substrate-assisted proton displacement mechanism for catalysis, by re-evaluating the central role of Glu180 and the catalytic lysine, and identifying several active-site residues related to the mechanism. This discovery could be helpful in developing inhibitors for the enzyme or producing biocatalysts capable of changing the stereochemistry of molecules through enzyme engineering.
JOURNAL OF BIOLOGICAL CHEMISTRY
(2021)
Article
Biochemistry & Molecular Biology
Tanzeel Arif, Michael J. Currie, Renwick C. J. Dobson, Harriet L. Newson, Vivek Poonthiyil, Antony J. Fairbanks, Rachel A. North, Phillip M. Rendle
Summary: The synthesis of analogues of natural enzyme substrates can help deduce enzymatic mechanisms, as demonstrated by the investigation into N-acetylmannosamine-6-phosphate 2-epimerase. The study suggests that this enzyme may utilize a substrate-assisted proton displacement mechanism, with two novel analogues showing different binding orientations at the enzyme's active site.
CARBOHYDRATE RESEARCH
(2021)
Correction
Biochemistry & Molecular Biology
Moritz Lasse, Anja R. Stampfli, Thomas Orban, Roshit K. Bothara, Juliet A. Gerrard, Antony J. Fairbanks, Neil R. Pattinson, Renwick C. J. Dobson
BIOCHIMICA ET BIOPHYSICA ACTA-GENERAL SUBJECTS
(2022)
Article
Chemistry, Organic
Xin Qiu, Daniel Chong, Antony J. Fairbanks
Summary: Unprotected sugars can be selectively acetylated in aqueous solution by stirring with acetic anhydride and a weak base, such as sodium carbonate. This reaction specifically targets the anomeric hydroxyl group of mannose, 2-acetamido, and 2-deoxy sugars and can be conducted on a large scale. However, over-reaction and the formation of product mixtures can occur due to competitive intramolecular migration of the 1-O-acetate to the 2-hydroxyl group when these two substituents are in cis configuration.
Article
Chemistry, Multidisciplinary
Xin Qiu, Anna L. Garden, Antony J. Fairbanks
Summary: In this study, a new method for synthesizing glycosides was discovered. Unprotected 2-acetamido sugars were directly converted into their oxazolines in aqueous solution using 2-chloro-1,3-dimethylimidazolinium chloride (DMC) and a suitable base. Freeze drying and acid-catalyzed reaction with an alcohol as solvent yielded 1,2-trans-glycosides in good yield. Alternatively, using an aprotic solvent system and acidic activation with an excess of unprotected glycoside as a glycosyl acceptor led to the stereoselective formation of 1,2-trans-linked disaccharides without any protecting group manipulations. Reactions using aryl glycosides as acceptors were completely regioselective, producing only (1->6)-linked disaccharides.
Meeting Abstract
Biochemistry & Molecular Biology
Sivasinthujah Srikokulan, Antony Fairbanks
Article
Chemistry, Organic
Xin Qiu, Antony J. Fairbanks
ORGANIC & BIOMOLECULAR CHEMISTRY
(2020)
Article
Chemistry, Multidisciplinary
Mikkel Haarslev Schroder Marqvorsen, Sivasinthujah Paramasivam, Ward Doelman, Antony John Fairbanks, Sander Lzaak van Kasteren
CHEMICAL COMMUNICATIONS
(2019)