Facile Anomer-oriented Syntheses of 4-Methylumbelliferyl Sialic Acid Glycosides

13 April 2021, Version 1
This content is a preprint and has not undergone peer review at the time of posting.


As part of a program to find new sialidases and determine their enzymatic specificity and catalytic activity, a library of 4-methylumbelliferyl sialic acid glycosides derivatised at the C-5 position were prepared from N-acetylneuraminic acid. Both α- and β-4-methylumbelliferyl sialic acid glycosides were prepared in high yields and excellent stereoselectivity. Alpha anomers were accessed via reagent control by utilising additive CH3CN and TBAI, whereas the beta anomers were synthesised through a diastereoselective addition reaction of iodine and the aglycone to the corresponding glycal followed by reduction of the resulting 3-iodo compounds. Both anomer-oriented synthetic pathways allow for gram-scale stereoselective syntheses of the desired C-5 modified neuraminic acid derivatives for use as tools to quantify the enzymatic activity and substrate specificity of known sialidases, and potential detection and investigation of novel sialidases.


Carbohydrate chemistry
chemoenzymatic synthesis
chemoenzymatic method

Supplementary materials

Supplementary Info 4-methylumbelliferyl sialic acid


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