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Varki A, Cummings RD, Esko JD, et al., editors. Essentials of Glycobiology [Internet]. 4th edition. Cold Spring Harbor (NY): Cold Spring Harbor Laboratory Press; 2022. doi: 10.1101/glycobiology.4e.55
Structure of neuraminidase inhibitors. Chemical structure of sialic acid (Neu5Ac, 2-deoxy-2,3-dehydro-N-acetyl neuraminic acid), DANA; 4-amino-DANA; 4-guanidino-DANA (Relenza, zanamivir); (3R, 4R, 5S)-4-acetamido-5-amino-3-(1-ethylpropoxyl)-1-cyclohexane-1-carboxylic acid ethyl ester (Tamiflu, oseltamivir), C9-4HMT-DANA and FaxGuDFSA. DANA is thought to resemble the transition state in hydrolysis, and addition of the guanidinium group in Relenza provides higher affinity binding to the active site. The ethyl ester in Tamiflu enhances oral availability and then is quickly removed in the body by nonspecific esterases. C9-4HMT-DANA is a selective inhibitor of human neuraminidase 4, and FaxGuDFSA is an example of a non-DANA-like scaffold that inhibits viral neuraminidases.
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From: Chapter 55, Chemical Tools for Inhibiting Glycosylation
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