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Progress in Chemistry 2022, Vol. 34 Issue (7): 1548-1553 DOI: 10.7536/PC220231 Previous Articles   Next Articles

• Review •

Challenges in Chemical Synthesis of Glycans and the Possible Problems Relevant to Condensed Matter Chemistry

Peng Xu(), Biao Yu()   

  1. State Key Laboratory of Bioorganic and Natural Product Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Science,Shanghai 200032, China
  • Received: Revised: Online: Published:
  • Contact: Peng Xu, Biao Yu
  • Supported by:
    the National Natural Science Foundation of China(22177125); Science and Technology Commission of Shanghai Municipality(22ZR1475600)
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Glycans are the most abundant organic polymers in nature, and vital biomaterials for structural support and energy storage in living organisms. Meanwhile, glycans play an important role in cell recognition, differentiation, development, carcinogenesis and immunity. Compared with nucleic acid and protein, the specific role of glycans in many biological processes is still unknown, which is related to the difficulty of accessing well-defined glycans and the lack of precise tools for manipulating glycans in vivo. Synthetic methods in carbohydrate chemistry have been developed rapidly in recent decades, providing a powerful weapon for the study of synthetic glycans, especially oligosaccharides. Nevertheless, compared with the synthesis of nucleic acids and proteins, the synthesis of structurally well-defined glycans remains an unsolved chemical challenge with many unexpected problems. There are various factors that may affect the efficiency and stereoselectivity of glycosylation profile. Furthermore, glycans could be assembled into ordered aggregates through intermolecular non-covalent forces, then affecting the synthesis. For instance, in the process of removal protecting groups, the great change of solubility of glycan has a decisive effect on the reaction. The effect of aggregation formation on reactivity has not been thoroughly studied. Therefore, it is still necessary to complete the synthesis of well-defined glycan through trial-and-error experiments. In addition, glycans and glycoconjugates play an important role in living organisms by forming supramolecular structures. In conclusion, it is of great significance to study the condensed matter chemistry in glycans and their synthesis.

Contents

1 Structure, function and synthesis of glycans in living systems

2 Challenges and advances in the chemical synthesis of glycans

3 Some uncertainties in the chemical synthesis of glycans

3.1 The solvent effect

3.2 The concentration effect

3.3 The temperature effect

3.4 Problems in heterogeneous reactions

3.5 Solubility problem

4 Possible condensed matter chemistry problems

5 Prospect

Key words: glycans, chemical synthesis, aggregation, solubility, condensed matter chemistry
Fig. 1 Protein glycosylation and the glycan-involved interactions[2]
Fig. 2 Glycan synthesis by condensation polymerization[14]. Ac = acetyl[14]
Fig. 3 Stereoselective synthesis of α- decaglucan based on a concentration effect[17]. Bn = benzyl, Bz = benzoyl, Tol = p-methylphenyl
Fig. 4 Template directed cyclo-glycosylation with the stereoselectivity being effected by the reaction temperature[21]. Me = methyl, TBDPS = tert-butyldiphenylsilyl
Fig. 5 1,2-cis Selective glycosylation in the presence of different dehydrating agents[23]
Fig. 6 Deprotection of glycans relevant to the O-antigen of Bacteroides vulgatus[25f]. Ph = phenyl, TBS = tert-butyldimethyl, MP = p-methoxyphenyl
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