Thioglycosides have important value as stable glycoside analogues in a range of studies of glycosidases. CD BioGlyco has accumulated abundant experience in custom thioglycoside synthesis and we are capable of providing our clients with the necessary scientific assistance in the field of glycobiology.

Background

Thioglycosides are glycoside oxygen atoms substituted by sulfur atoms. Due to their high stability in organic chemical operations, they have been extensively studied as useful glycosyl donors. The thioglycosides function as temporary protective groups at the anomeric position, which allows the thioglycosides to act as both glycosyl donors and glycosyl acceptors.

Thioglycosides have been synthesized by various routes such as the glycosylation of thio acceptors with activated glycosyl donor, SN2 reaction of 1-thio sugars with activated receptor and Michael addition reaction of 1-thiosugars to a,b-unsaturated system. All of these pathways involve many protection and deprotection steps, requiring good control of the stereochemistry of anomeric. In addition, enzymatic synthesis is a green and valuable method for the synthesis of thioglycosides. For example, using Ca(OH)₂ as an accelerator to glycosylate fluoride donors and thiol sugar acceptors, providing a variety of thioglycosides with good yield and exclusive stereoselectivity.

Fig.1 Enzymatic synthesis of thioglycosides. (Jahn, 2003)

Synthesis Services

CD BioGlyco provides our clients with exact custom synthesis service of thioglycosides with high quality and purity through a variety of synthesis routes including chemical and enzymatic synthesis techniques. The services we can provide include but are not limited to:

• Providing chemical synthesis service of thioglycosides. Thiophilic metal salts such as Hg(NO₃)₂, Hg(OBz)₂ and HgCL₂, arylselenylating agents such as PhSeNPhth—TMSOTf, PhSeOTf, PhSeNPhth–Mg(ClO₄)₂, alkylating agents such as Mel and MeOTf, and some oxidative agents are used as glycosidation promoters of thioglycosides.
• Providing enzymatic synthesis service of thioglycosides. We customized the synthesis of thioglycosides for customers according to the advanced synthesis method in this field, such as using retaining glycosidases lacking catalytic acid-base amino acid residues to synthesis S-glycosidic linkages in oligosaccharides.

Advantages of Us

• Professional team specialize in thioglycosides synthesis
• Providing a variety of synthesis routes for your choice
• Efficient, fast and practical service
• Detailed and reliable after-sales service

CD BioGlyco relies on its first-class experimental platform and recognized expertise to provide high-quality one-stop services for the synthesis of thioglycosides. We tailor the most rational experimental procedures to meet our clients' research needs and supply detailed experimental protocols and reports on the results of the final products. If you are interested in our services, please contact us and send us your inquiry.

References:

1. Jahn, M.; et al. Thioglycoligases: Mutant Glycosidases for Thioglycoside Synthesis. Angewandte Chemie International Edition. 2003, 20;42(3):352-4.
2. Gao-Lan, Z.; et al. Protecting-group-free S-glycosylation towards thioglycosides and thioglycopeptides in water. Green Chemistry. 2021, 21;23(8):2907-2912.