User:Nicolezakharov/Glycoside/Bibliography

Glycans are involved in various biological processes, including disease pathways. C-glycosides are un-natural glycan analogues where the glycosidic oxygen is replaced with a carbon substituent. •C-glycosides are cyclic ethers and not acetals as their parent O-glycosides. They are more stable to chemical and enzymatic hydrolysis since the anomeric position is now a carbon substituent. So, they are extensively used as mechanistic probes and potential therapeutics. They have different conformational and receptor binding properties than their O-glycosidic counterpart. In most cases they have higher efficacy and are better drugs like the example show.If you need to be convinced take for example the case of alpha galactose ceramide, the famous anticancer drug, alphagalactose ceramide. The c-analogue was comparied with its parent o-glycoside In treatment of the mouse malaria and melanoma model. In both cases the c-glycoside shoes to have better drug efficacy then the o-glycoside. In the mouse malaria model, they treated sporozoites with both the c-glycoside and the o-glycoside and after 42 hours the c-glycoside was significanly better at treating the sporozoited then theoglycoside.Similirly, in the melanoma model, skin treated with the c-glycoside showed much better results than treatment with the o-glycoside at the same dosage.

Schmieg, et al. J. Exp. Med. 2003, 198, 1631–164

Dall’Olio, F.; Pucci, M.; Malagolini, N. et.al Cancers. 2021, 13 (21), 5273.