Design, Synthesis and Applications of C-glycosyl Derivatives

Dear Colleagues,

C-Glycosyl compounds are structurally characterized by a carbon-carbon bond between the (former) anomeric center of a glycon with either pyranoid or furanoid ring and an aglycon which can be of any kind such as aliphatic and aromatic moieties including heterocycles and even sugars. Contrary to O-glycosides that have a glycosidic linkage of acetalic nature between the glycon and the aglycon, C-glycosyl derivatives are considerably stable since the acetal moiety is no more present in the molecule. The resistance of such compounds towards chemical or enzymatic hydrolysis renders them to one of the most widely used types of glycomimetics. Such compounds can be used among others as glycoenzyme inhibitors and lectin antagonists, and frequently serve as leads in drug design. A remarkable achievement in the latter field during the last decade was the success of gliflozins with a C-glycosylarylmethyl arene skeleton as antidiabetics acting by an untargeted biological mechanism to relieve high blood sugar levels. C-Glycosyl compounds also occur in nature and have been used in the development of nucleoside modified mRNA vaccines as well as antiviral medications against COVID-19. A large number of surveys deal with the synthesis and properties of C-glycosyl derivatives. The most recent comprehensive reviews were published some five years ago to summarize general synthetic methods (Chem. Rev., 2017, 117, 12281), uses in natural product syntheses (Chem. Rev., 2018, 118, 1495) and preparation and antidiabetic applications of C-glycosyl (het)arenes (Chem. Rev., 2017, 117, 1687). The large number of citations these reviews have received indicate the very high relevance of and the continuing activity in this field of research. The aim of the present special issue is to collate high level papers (original research articles and reviews) presenting up-to-date investigations in the design, synthesis and applications of C-glycosyl derivatives in the broadest sense including interdisciplinary studies.

Prof. Dr. László Somsák
Guest Editor

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• C-glycosyl compound
• C-nucleoside
• synthesis
• isolation
• application
• computation
• modelling
• enzyme inhibitor
• lectin antagonist
• drug design