The effect of neighbouring group participation and possible long range remote group participation in O-glycosylation

• Rituparna Das and
• Balaram Mukhopadhyay

Beilstein J. Org. Chem. 2025, 21, 369–406, doi:10.3762/bjoc.21.27

• [48]. The review will primarily be referring to axial or α-glycosides as 1,2-cis glycosides except for mannosides where the term β-mannosides will be used for 1,2-cis-mannoside configuration, respecting the complexity and novelty they bring to the world of synthetic glycochemistry. The spanning of the

• ] and corresponding automated oligosaccharide synthesis [63][64][65]. These procedures pave the way for the new generation of glycomics and glycochemistry which promises to show new paths towards deciphering the unsolved mysteries of nature [66]. There have been many reviews in literature showcasing the

• much studied topic in synthetic glycochemistry [162][163][164]. The effects attributed by the remote groups may also be the summative effect of other factors like steric hindrance, conformational hindrance, or other stereoelectronic factors. However, in this article we have tried to show all the

Red light excitation: illuminating photocatalysis in a new spectrum

• Lucas Fortier,
• Corentin Lefebvre and
• Norbert Hoffmann

Beilstein J. Org. Chem. 2025, 21, 296–326, doi:10.3762/bjoc.21.22

• Lucas Fortier Corentin Lefebvre Norbert Hoffmann Unité de Catalyse et de Chimie du Solide (UCCS), University of Lille, CNRS, University of Artois UMR 8181, Avenue Mendeleiev, 59655 Villeneuve d’Ascq CEDEX, France Laboratory of Glycochemistry and Agroressources of Amiens (LG2A), University of

Comparison of glycosyl donors: a supramer approach

• Anna V. Orlova,
• Nelly N. Malysheva,
• Maria V. Panova,
• Nikita M. Podvalnyy,
• Michael G. Medvedev and
• Leonid O. Kononov

Beilstein J. Org. Chem. 2024, 20, 181–192, doi:10.3762/bjoc.20.18

• Anna V. Orlova Nelly N. Malysheva Maria V. Panova Nikita M. Podvalnyy Michael G. Medvedev Leonid O. Kononov Laboratory of Glycochemistry, N.D. Zelinsky Institute of Organic Chemistry, Moscow, Russian Federation Theoretical Chemistry Group, N.D. Zelinsky Institute of Organic Chemistry, Moscow

Progress and challenges in the synthesis of sequence controlled polysaccharides

• Giulio Fittolani,
• Theodore Tyrikos-Ergas,
• Denisa Vargová,
• Manishkumar A. Chaube and
• Martina Delbianco

Beilstein J. Org. Chem. 2021, 17, 1981–2025, doi:10.3762/bjoc.17.129

• solution phase using block coupling [165]. α-Glucans In contrast to the relatively simple formation of a 1,2-trans glycosidic bond using participating group at C-2, the construction of 1,2-cis glycosidic bonds is a long-standing challenge in the field of glycochemistry [167]. The formation of 1,2-cis Glc

Synthesis of 1,4-imino-L-lyxitols modified at C-5 and their evaluation as inhibitors of GH38 α-mannosidases

• Maroš Bella,
• Sergej Šesták,
• Ján Moncoľ,
• Miroslav Koóš and
• Monika Poláková

Beilstein J. Org. Chem. 2018, 14, 2156–2162, doi:10.3762/bjoc.14.189

• Maros Bella Sergej Sestak Jan Moncol Miroslav Koos Monika Polakova Department of Glycochemistry, Institute of Chemistry, Slovak Academy of Sciences, Dúbravská cesta 9, SK-845 38, Bratislava, Slovakia Department of Inorganic Chemistry, Faculty of Chemical and Food Technology, Radlinského 9, SK-812

Anomeric modification of carbohydrates using the Mitsunobu reaction

• Julia Hain,
• Patrick Rollin,
• Werner Klaffke and
• Thisbe K. Lindhorst

Beilstein J. Org. Chem. 2018, 14, 1619–1636, doi:10.3762/bjoc.14.138

• applications of the Mitsunobu reaction in glycochemistry have mostly dealt with the functionalization of the primary hydroxy group of sugars and, to a lesser extent, with modifications of the secondary alcohol array in carbohydrate rings [2][3][4][5][6], for example for halogenation [20]. However, the

Enzymatic synthesis of glycosides: from natural O- and N-glycosides to rare C- and S-glycosides

• Jihen Ati,
• Pierre Lafite and
• Richard Daniellou

Beilstein J. Org. Chem. 2017, 13, 1857–1865, doi:10.3762/bjoc.13.180

• of rare or unnatural glycosidic linkages. Keywords: enzyme; glycochemistry; glycoside hydrolase; glycosyltransferase; mechanism; Introduction The role of glycoconjugates is of prime importance, as they are nowadays well known to mediate many biological processes [1]. As a consequence, in a recently

• . Rational mutagenesis, directed evolution, or even de novo design have dramatically broaden the applicability of enzymes in biocatalysis [7]. In the glycochemistry field, a vast array of carbohydrate-metabolizing enzymes [8] has been used to synthesize glycosides, even using multiple enzymes systems

Synthesis of 1,2-cis-2-C-branched aryl-C-glucosides via desulfurization of carbohydrate based hemithioacetals

• Henok H. Kinfe,
• Fanuel M. Mebrahtu,
• Mandlenkosi M. Manana,
• Kagiso Madumo and
• Mokela S. Sokamisa

Beilstein J. Org. Chem. 2015, 11, 583–588, doi:10.3762/bjoc.11.64

• glycochemistry and medicinal chemistry [1][2][3][4][5]. C-Glycosides, especially aryl-C-glycosides, are the main structural features of a number of biologically active natural products such as pluramycins (antibacterial and antitumor activities), angucyclines (antibacterial, antitumor activities, and inhibitors

Synthesis of enantiopure sugar-decorated six-armed triptycene derivatives

• Paola Bonaccorsi,
• Maria Luisa Di Gioia,
• Antonella Leggio,
• Lucio Minuti,
• Teresa Papalia,
• Carlo Siciliano,
• Andrea Temperini and
• Anna Barattucci

Beilstein J. Org. Chem. 2013, 9, 2410–2416, doi:10.3762/bjoc.9.278

• applications not only as glycoconjugates in glycochemistry, but also as interesting candidates for host–guest interactions by presenting a rigid lipophilic core surrounded by hydrophilic sugar moieties assembled on a rotor skeleton. The six-armed sugar-decorated triptycene derivatives might constitute a new

The use of glycoinformatics in glycochemistry

• Thomas Lütteke

Beilstein J. Org. Chem. 2012, 8, 915–929, doi:10.3762/bjoc.8.104

• that can be of use to glycobiologists, but also to chemists who work on the synthesis or analysis of carbohydrates. This article gives an overview of existing glyco-specific databases and tools, with a focus on their application to glycochemistry: Databases can provide information on candidate glycan

• analysis of carbohydrates and other glyco-related experiments. The protocols include step-by-step instructions, references, and features to rate the protocols or to post related questions. Another resource with a special focus on glycochemistry is GlycoNavi, which is a database of chemical reactions that