A series of advances have been made in the study of glycochemical synthesis.

Sugar compounds play a very important role in many life processes, such as bacterial and viral infections, cell growth and proliferation, immune response, etc.
Compared to gene-regulated biosynthetic proteins and DNA, biosynthetics of sugar compounds are not genetically regulated, but rather through a step-by-step and enzyme-retransfring process in the internal network and gouldyl bodies, resulting in the unorthodox and extremely diverse structure of sugar compounds.
it is a very difficult task to separate and extract pure and structural polysaccharies from nature.
chemical synthesis is an effective and scalable way to obtain pure and structurally determined sugar compounds that can be studied in depth and new therapeutic drugs can be developed.
, however, the chemical synthesis of sugar molecules is much more backward and difficult than the easy preparation of nucleotides and peptides through automated solid-phase synthesizers.
Xiao Guozhi of the Natural Product Synthesis Chemistry Team of Kunming Plant Research Institute of the Chinese Academy of Sciences mainly carried out the research work of glycochemical synthesis from the following two aspects: (1) developing new methods and strategies of glycochemical synthesis;
2019, the team reported on an orthosopolycosided reaction strategy based on glyco-based phthalates (Glycoside reactions) (Org. Lett. 2019, 21, 2335)。
this strategy solves the problem of sulfur glycoside metastasis, departure group interference and large taste of thiol, which is previously synthesized by the orthosososide-based one-pot method, and greatly widens its application range.
first author of this research is Zhang Yunqin, a doctoral student.
the beginning of this year, the team developed a novel glycosided reaction that enables efficient synthesis of oxycosides and nucleosides (Nat. Commun. 2020, 11, 405)。
This method uses easy-to-prepare and stable glyco-based neighbor 1-benzene benzoate (PVB) as a novel glycosyl token, N-iodine-detide diamide (NIS) and TMSOTf as cheap and readable promoters, while having a mild, wide substrate range and good to excellent glycoside reaction yield.
It is worth mentioning that PVB ligation can be combined with triclosan acetylamide (TCAI) to the body (Schmidt glycoside reaction), glyco-based phthalates (ABz) to the body (ABz glycosided reaction) to carry out ortholycosided reaction, to achieve a variety of important physiological activities of oligosaccharides efficient synthesis.
addition, PVB ligands can also be successfully used in the highly efficient synthesis of nucleoside antibiotic drugs capedabin, Gallothabin and deoxyfluorourourine.
the first authors of this research are Ph.D. student Li Penghua, Ph.D. He Haiqing and Ph.D. graduate student Zhang Yunqin.
Recently, Xiao Guozhi task force reported the use of the previously developed orthographic pot glycoside reaction strategy to achieve a strong anti-diabetic guava polysaccharide 19 sugar repeat unit and substructive high-efficiency synthesis, so that it can further study its biological activity, for the future development of diabetes drugs to lay a solid foundation.
the study was published online by Angew. Chem. Int. Ed. (DOI: 10.1002/anie.202000992).
first authors of this research are Ph.D. students Zhang Yunqin, Chen Zixi and Huang Yingying.
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