Article
Chemistry, Organic
Ananya Mukherji, Mahendra K. V. Rotta, Bikash K. Sarmah, Pavan K. Kancharla
Summary: This study investigates the influence of different silyl protecting groups (TBDMS, TIPS, and TBDPS) on 2-deoxyrhamnosylation. It is found that the TIPDS protecting group exhibits complete alpha-selectivity in C-glycosylation reactions. In contrast, the TBDPS protecting group shows superior protection for alpha-stereoselective O-glycosylation reactions with various acceptors.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Yasmeen Bakhatan, Israel Alshanski, Chieh-Kai Chan, Wei-Chih Lo, Po-Wei Lu, Pin-Hsuan Liao, Cheng-Chung Wang, Mattan Hurevich
Summary: Solid-phase synthesis is the main method for preparing biological oligomers. Accelerated solid-phase synthesis is crucial for chemical biology but is not easy for oligosaccharide synthesis. High shear stirring is a new approach to accelerate solid-phase synthesis by improving mixing efficiency. In this study, we used high shear mixing to perform diffusion-dependent glycosylation and completed full glycosylation cycles in minutes.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Review
Biotechnology & Applied Microbiology
Zorica Ubiparip, Marc De Doncker, Koen Beerens, Jorick Franceus, Tom Desmet
Summary: Beta-glucan phosphorylases are important carbohydrate-active enzymes with great potential for the biocatalytic synthesis of beta-glucans. Their preference for sugar phosphates highlights their significance in the carbohydrate industry.
APPLIED MICROBIOLOGY AND BIOTECHNOLOGY
(2021)
Article
Chemistry, Multidisciplinary
Dawei Dong, Yafei Xiao, Minghua Zhang, Peixin Gong, Yingqing Ye, Shuhua Peng, Ke Wang, Minmin Fan
Summary: Polysaccharide is a complex biological macromolecule that plays an irreplaceable role in organisms. This study synthesized glucan polysaccharide using a green and efficient solid-phase polymerization method, and characterized the resulting product. It was found to have mainly linear structure with various glycosidic linkages.
ACS SUSTAINABLE CHEMISTRY & ENGINEERING
(2022)
Article
Chemistry, Multidisciplinary
Hugo Minnee, Johannes G. M. Rack, Gijsbert A. van der Marel, Herman S. Overkleeft, Jeroen D. C. Codee, Ivan Ahel, Dmitri V. Filippov
Summary: ADP-ribosylation is a process that transfers an ADP ribose moiety to a nucleophilic side chain by consuming nicotinamide adenine dinucleotide, allowing for the regulation of key processes such as apoptosis and DNA repair. Recent studies have identified histidine as an acceptor site for ADP-ribose, leading to the development of a synthetic strategy for ADP-ribosylated histidine peptides. The stability and resistance of these peptides against chemical conditions and degradation by ADP-ribosylhydrolases have been investigated, showing promising results for their application in further research.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Samira Escopy, Yashapal Singh, Keith J. Stine, Alexei V. Demchenko
Summary: As the 21st century unfolds with rapid changes, new challenges have arisen in research and development. This article introduces a solution phase batch synthesis method based on the HPLC platform, which enables sequential synthesis of multiple oligosaccharides and automates the process.
CHEMISTRY-A EUROPEAN JOURNAL
(2022)
Article
Chemistry, Multidisciplinary
Xiaona Li, You Yang
Summary: Automated chemical solid-phase synthesis is a reliable and efficient automation platform for synthesizing glycans. Automated Glycan Assembly (AGA), as a key breakthrough in the field, has evolved from a proof-of-concept to a robust technology for streamlined production of various glycans. In addition, HPLC-assisted automated synthesis shows promising potential in accessing glycans.
CHINESE JOURNAL OF CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Kim Greis, Sabrina Leichnitz, Carla Kirschbaum, Chun-Wei Chang, Mei-Huei Lin, Gerard Meijer, Gert von Helden, Peter H. Seeberger, Kevin Pagel
Summary: The study investigates how the electron density in acyl protecting groups influences the stereoselectivity, revealing that electron-rich acylated galactose building blocks show higher alpha-selectivity, while counterparts with electron-withdrawing groups exhibit lower selectivity. Further research is needed to explore the mechanism behind this phenomenon.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2022)
Article
Chemistry, Multidisciplinary
Sabrina Leichnitz, Komadhie C. Dissanayake, Arthur H. Winter, Peter H. Seeberger
Summary: Protective groups that can be selectively removed under mild conditions are important in carbohydrate chemistry. This study explores different BODIPY protecting groups for their usefulness in glycan synthesis. A BODIPY group with a boron difluoride unit is stable during glycosylations but can be cleaved with green light, as demonstrated by the assembly of a trisaccharide.
CHEMICAL COMMUNICATIONS
(2022)
Article
Chemistry, Multidisciplinary
Tao Wang, Xiuxiu Cao, Yong Zheng, Chenchen Chen, Li Zhou, Demeng Sun, Gemin Fang, Changlin Tian
Summary: A practical strategy for the total stepwise solid-phase synthesis of peptide-oligonucleotide conjugates was developed using Boc/tBu protecting groups for specific amino acids. This strategy avoids depurination of the oligonucleotide caused by strong acid treatment and allows for easier availability of the necessary amino acids. The side reaction of deguanidination of the Arg residue can also be avoided with this protection strategy.
CHEMICAL COMMUNICATIONS
(2023)
Article
Chemistry, Organic
Dhananjani N. A. M. Eriyagama, Yipeng Yin, Shiyue Fang
Summary: Automated stepwise synthesis of polyethylene glycols (PEGs) was successfully achieved using a modified peptide synthesizer and a monomer with a base-labile protecting group. The automated assembly of PEGs was accomplished by deprotonation of the alcohol group on the solid support followed by reaction with the monomer. This method can be adapted for the synthesis of various sequence-defined oligomers and polymers.
Article
Chemistry, Organic
Kim Greis, Carla Kirschbaum, Giulio Fittolani, Eike Mucha, Rayoon Chang, Gert von Helden, Gerard Meijer, Martina Delbianco, Peter H. Seeberger, Kevin Pagel
Summary: This study investigates the influence of fluorination on the structure of the glycosyl cation, an intermediate in glycosylation reactions. The results reveal that C3 and C6 fluorination of glucosyl building blocks can alter the structure of the glycosyl cation, with neighboring group participation being the dominant motif.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Xiaoqian Li, Zhi Ma, Rongkun Liu, Mattan Hurevich, You Yang
Summary: A green and efficient photolabile protecting group (PPG)-mediated glycosidation approach for the synthesis of 2-deoxy-glycosides is reported. Multiple oNBC groups in the 2-deoxy-glycosides can be completely cleaved by irradiation at 365 nm, resulting in the desired 2-deoxy-glycosides in an efficient manner. Oligosaccharides with three to six oNBC groups are effectively achieved based on this PPG-mediated glycosidation approach.
CHINESE JOURNAL OF CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Bingxin Liang, Rong Li, Linji Li, Ming Tang, Xiang Li, Chunli Su, Hongli Liao
Summary: Cyclization and glycosylation are effective methods for enhancing the drug properties of peptides. Atypical arginine N-glycosylation has gained attention due to its role in cellular processes and signaling pathways. This study describes the synthesis of an arginine glycosylated cyclopeptide analog using solid-phase glycosylation and solution-phase cyclization, resulting in enhanced water solubility compared to the non-glycosylated peptide. This method provides a universal strategy for synthesizing arginine N-glycosylated cyclopeptides.
FRONTIERS IN CHEMISTRY
(2023)
Article
Biochemistry & Molecular Biology
Alexanndra Behm, Jessica Hafner, Natalie Goeckner, Matthew Lohman, Cristina De Meo
Summary: In this study, the reactivities of phenylthio alpha- and beta-sialyl donors protected at C-4 with tert-butyldimethyl silyl (TBDMS) and tri-isopropylsilyl (TIPS) groups in coupling reactions with different types of galactosyl acceptors were compared. The effect of solvent and donor's anomeric configuration on the reactions were investigated. The results demonstrate the significant influence of silicon groups at C-4 in sialylation reactions, with overall performance optimized using acetonitrile.
CARBOHYDRATE RESEARCH
(2022)
Article
Chemistry, Multidisciplinary
Stefan Matthies, Pierre Stallforth, Peter H. Seeberger
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2015)
Article
Chemistry, Organic
Stefan Matthies, D. Tyler McQuade, Peter H. Seeberger
Article
Chemistry, Organic
Markus W. Weishaupt, Stefan Matthies, Mattan Hurevich, Claney L. Pereira, Heung Sik Hahm, Peter H. Seeberger
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
(2016)
Article
Chemistry, Multidisciplinary
Gregory B. Craven, Dominic P. Affron, Charlotte E. Allen, Stefan Matthies, Joe G. Greener, Rhodri M. L. Morgan, Edward W. Tate, Alan Armstrong, David J. Mann
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2018)
Article
Chemistry, Multidisciplinary
Pierre Stallforth, Stefan Matthies, Alexander Adibekian, Dennis G. Gillingham, Donald Hilvert, Peter H. Seeberger
CHEMICAL COMMUNICATIONS
(2012)
Review
Chemistry, Multidisciplinary
Moritz F. Kuehnel, Philipp Holstein, Meike Kliche, Juliane Krueger, Stefan Matthies, Dominik Nitsch, Joseph Schutt, Michael Sparenberg, Dieter Lentz
CHEMISTRY-A EUROPEAN JOURNAL
(2012)
Meeting Abstract
Biochemical Research Methods
S. Matthies, F. Maier
JOURNAL OF LABELLED COMPOUNDS & RADIOPHARMACEUTICALS
(2010)