CD BioGlyco has accumulated rich experience in HMO chemical synthesis and provides high-quality HMO production services. Welcome clients from all over the world to cooperate with us!

Development of Chemical Synthesis of HMOs

• In general, the main protecting groups used in the chemical synthesis of HMOs are benzoyl, benzyl, and acetic esters. And after the protection step, glycosidic bond formation is performed using chemical catalysts, such as triethylsilyl trifluoromethanesulfonate (TESOTf), N-iodosuccinimide (NIS), and silver trifluoromethanesulfonate (AgOTf). Finally, the protected HMO structure must be deprotected to obtain the desired molecule.
• As early as 1999, scientists used chemical methods for the first time to synthesize lacto-N-tetraose and lacto-N-neotetraose through 34 steps of the reaction. In the past two decades, scientists have extensively used chemical synthesis methods through continuous exploration and attempt to increase the yield of oligosaccharides.

Fig.1 Yun's group first attempted assembly of LNnH. (Bandara, et al., 2020)

Advantages of Chemical Synthesis of HMOs

Chemical synthesis can initially provide some common precursors for chemoenzymatic methods to its accompanying toxicity of reagents and complex reaction conditions, and better exert its advantages. The basic strategy of this method is to control the activity of donors and receptors so that two-step or multi-step glycosylation can be carried out continuously, thus avoiding complicated protection, deprotection operations, and separation and purification of intermediates in the reaction process, and greatly improving the yield.

HMO Production by Chemical Methods at CD BioGlyco

We provide a wealth of synthesis techniques, including but not limited to the following:

• Fully automatic solid-phase synthesis

In solid phase synthesis, the oligosaccharide is connected to an insoluble substance, which can realize rapid separation of reaction products and excessive reactants. This technology is usually used to synthesize oligosaccharides with determined structures.

• Crystallization media technology
• It helps the purification in the operation of protecting sugar and deprotecting sugar. This method is used to rapidly synthesize some specific oligosaccharides, such as 2'FL.
• One pot method

Generally, simple raw materials are used to conduct multi-step reactions in a reactor to directly and efficiently obtain compounds with complex structures.

CD BioGlyco offers the production of various HMO types by chemical synthesis, including but not limited to the following:

In the field of chemical synthesis of HMO, CD BioGlyco made many achievements, which are widely praised by clients internationally. If you are interested in our services, please contact us for more details.

References

1. Pérez-Escalante, E.; et al. Human milk oligosaccharides as bioactive compounds in infant formula: recent advances and trends in synthetic methods. Critical Reviews in Food Science and Nutrition. 2022, 62(1): 181-214.
2. Bandara, M.D.; et al. Chemical synthesis of human milk oligosaccharides: lacto-N-neohexaose (Galβ1→ 4GlcNAcβ1→) 2 3, 6Galβ1→ 4Glc. Organic & biomolecular chemistry. 2020, 18(9): 1747-1753.