Article
Biochemistry & Molecular Biology
Yang-Fan Guo, Tao Luo, Guang-Jing Feng, Chun-Yang Liu, Hai Dong
Summary: An improved method for efficiently synthesizing 2-OH thioaryl glycosides from per-protected glycals was developed. The method involved the oxidation of glycals with oxone to prepare 1,2-anhydro sugars, followed by reaction with NaBH4 and aryl disulfides. This method was also used in a one-pot reaction to synthesize glycosyl donors with both armed and NGP effects.
Article
Chemistry, Organic
Bryant Pero, Mark W. Peczuh
Summary: A new synthesis of carbohydrate-based oxepines using 2,3;4,6-di-O-acetonide mannose as a key starting material is reported. The oxepine is an important precursor used in the synthesis of septanose glycomimetics of mannopyranosides.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Yongliang Wei, Benjamin Ben-zvi, Tianning Diao
Summary: C-aryl glycosyl compounds offer improved in vivo stability compared to O- and N-glycoside analogues, making them attractive candidates for drug development and chemical biology studies. A new cross-coupling method has been developed for the preparation of C-aryl and heteroaryl glycosides, including nucleosides and 2-deoxysugars, from easily accessible glycosyl esters and bromoarenes, demonstrating the potential of this method in medicinal chemistry.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Review
Plant Sciences
Richard Strasser, Georg Seifert, Monika S. Doblin, Kim L. Johnson, Colin Ruprecht, Fabian Pfrengle, Antony Bacic, Jose M. Estevez
Summary: Glycosylation is a crucial modification process that can alter the biological function of proteins and lipids, affecting the development and physiology of an organism. While challenges remain in understanding plant glycosylation, high throughput approaches may help to address these gaps, revolutionizing the identification and characterization of unknown plant glycosyltransferases and hydrolases.
FRONTIERS IN PLANT SCIENCE
(2021)
Article
Biochemistry & Molecular Biology
Levente Homolya, Laszlo Juhasz, Laszlo Somsak
Summary: The study focused on the addition of bromine and chlorine to O-peracylated glycals, resulting in mainly 2,3-trans-diaxial (3-bromo-3-deoxy-alpha-D-heptopyranosylbromide)onic acid derivatives. Despite successful glycosylation reactions, most attempted nucleophilic substitution and elimination reactions only yielded the parent glycal.
CARBOHYDRATE RESEARCH
(2021)
Article
Chemistry, Multidisciplinary
Pradip Das, Mosidur Rahaman Molla, Amit Kumar, Rima Thakur
Summary: The study reports an efficient and stereoselective synthesis of 2,3-dideoxy-beta-O-glycosides from C3-(o-cyanobenzoate) ester protected glycal donors via Ferrier rearrangement under Pd(0)-catalyzed Tsuji-Trost conditions. The stereo-chemical outcome of the reactions was independent of the nature of protecting groups or conformational flexibility of the glycal donors. Incorporation of the directing group on the benzoate ester altered the reactivity for Tsuji-Trost as well as Ferrier Rearrangement pathway.
CHEMISTRY-AN ASIAN JOURNAL
(2022)
Article
Chemistry, Multidisciplinary
Narayanaswamy Jayaraman
Summary: Unsaturated monosaccharides expand the reactivity scope in sugars, leading to new methodologies, molecular structures, and functional entities. Endocyclic or exocyclic unsaturation as reactive moieties can lead to largely unknown structures through one carbon homologations. Molecular shifts and rearrangements allow interchanging reactivities from one carbon to another in unsaturated sugars, with activations of exocyclic unsaturated sugars offering newer possibilities to sugar chemistry reactions. Personal reflections stem from decades of explorations in unsaturated sugars from varied perspectives.
Article
Chemistry, Organic
Perali Ramu Sridhar, Intzar Ali, M. V. Kamala Lakshmi
Summary: This study reveals an expeditious method for synthesizing monosaccharides and disaccharides with 3-oxo-glycal units. Several monosaccharides and disaccharide-derived glycals are converted to the corresponding hexenuloses through three steps involving halo-alkoxylate ion, dehydrohalogenation, and ketalyzation reactions. The importance and generality of the methodology are demonstrated by the synthesis of various 3-oxo-glycals. Additionally, the protocol is successfully applied to synthesize a rare-sugar disaccharide donor unit found in the reported natural product versipelostatin.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Anselme Geulin, Yann Bourne-Branchu, Kawther Ben Ayed, Thomas Lecourt, Antoine Joosten
Summary: 3-Amino-3-deoxyglycosides are important nitrogen-containing sugars, with many important ones having a 1,2-trans configuration. The synthesis of 3-amino-3-deoxyglycosyl donors that can form a 1,2-trans glycosidic linkage is a significant challenge due to their biological applications. This work presents a new sequence involving Ferrier rearrangement and subsequent aza-Wacker cyclization for the rapid synthesis of orthogonally protected 3-amino-3-deoxyglycals. Additionally, the epoxidation/glycosylation of a 3-amino-3-deoxygalactal derivative was successfully achieved with high yield and diastereoselectivity, demonstrating FAWEG as a new approach for accessing 1,2-trans 3-amino-3-deoxyglycosides.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Chemistry, Multidisciplinary
Weitao Yan, Mingwen Zheng, Peihsuan Chuang, Hao Sun, Shiping Wang, Chunfa Xu, Fen-Er Chen
Summary: A highly efficient coupling of glycosyl stannanes and sulfonium salts enabled by synergistic Pd/Cu catalysis has been developed for the construction of C-aryl/alkenyl glycals. This protocol demonstrates wide functional group tolerance and the one-pot formal C-H glycosylation starting from arene. Additionally, the successful gram-scale reaction indicates the high applicability of this method.
CHINESE CHEMICAL LETTERS
(2023)
Article
Chemistry, Multidisciplinary
Divya Rajendran, Jebasingh Bhagavathsingh
Summary: The study presents a convenient synthesis of O-galactosylation by reacting Boc-activated diphenols with alpha-bromoacetogalactose. The protection of amine and diphenolic hydroxyl group enhances the formation of galactosylated products in two steps. The yields of beta-isomer L-DOPA glycoside reach 72-84% through Boc-activation of hydroxyl group in diphenols.
Article
Chemistry, Multidisciplinary
Thomas Hansen, Tim P. Ofman, Joey G. C. Vlaming, Ivan A. Gagarinov, Jessey van Beek, Tessa A. Gote, Jacoba M. Tichem, Gijs Ruijgrok, Herman S. Overkleeft, Dmitri V. Filippov, Gijsbert A. van der Marel, Jeroen D. C. Codee
Summary: By systematically studying the reactivity-stereoselectivity relationships of caryophyllose donor and acceptor glycosides, using experimental and computational techniques, we were able to design carbohydrate building blocks with the necessary properties to assemble mycobacterial lipooligosaccharide fragments of M. marinum.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Analytical
Luyao Liu, He Zhu, Lei Liu, Xin You, Jiawei Mao, Yan Wang, Xiaoyan Liu, Hongqiang Qin, Mingming Dong, Mingliang Ye
Summary: Mucin-type O-glycosylation plays a vital role in regulating protein functions and biological processes, but its analysis is challenging due to the diverse and dense O-glycans. In this study, an O-glycopeptide truncation strategy using proteases or O-glycopeptidases was developed to simplify and enhance the analysis of O-GalNAc glycoproteomics.
ANALYTICAL CHEMISTRY
(2023)
Article
Chemistry, Analytical
He Zhu, Luyao Liu, Zheng Fang, Hongqiang Qin, Mingming Dong, Mingliang Ye
Summary: Different from N-linked glycosylation, the diversity and interpretation of O-linked glycans pose challenges. This study discovered Y-ion patterns in O-glycopeptide spectra, and proposed a search approach based on these patterns to identify O-glycopeptides. The approach constructs theoretical Y-ion patterns for matching experimental Y-ions, reducing search space and improving identification compared to existing software tools.
ANALYTICAL CHEMISTRY
(2023)
Article
Chemistry, Organic
Wei-Yi Ding, Hao-Wen Zhao, Jun Kee Cheng, Zhiqiang Lu, Shao-Hua Xiang, Bin Tan
Summary: This report describes a highly efficient beta-selective C-glycosylation reaction using bicyclic galactals and 2-oxindoles as substrates. The reaction proceeds through a palladium-catalyzed decarboxylative pathway under mild reaction conditions, resulting in high yields. The decarboxylation intermediate of galactal acts as an efficient base to deprotonate the enol tautomer of 2-oxindole, enhancing its nucleophilicity. The beta-selective nucleophilic addition at the anomeric center is due to steric hindrance imposed by the palladium and bulky ligand.
Article
Chemistry, Organic
Geeta Devi Yadav, Pooja Chaudhary, Balaram Pani, Surendra Singh
Summary: Chiral transition metal complexes with privileged ligands are efficient catalysts for various asymmetric organic transformations. Transition metal complexes of C1-symmetric pyrrolidine-based ligands have been widely used in asymmetric organic reactions. However, a comprehensive review article on the transition metal complexes of chiral C1-symmetric pyrrolidine-based ligands derived from (L)-proline has not been published.
TETRAHEDRON LETTERS
(2024)
