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Microfluidics-Based Ionic Catch and Release Oligosaccharide Synthesis (ICROS-Microflow) to Expedite Glycosylation Chemistry

Overview
Journal JACS Au
Specialty Chemistry
Date 2024 Nov 29
PMID 39610727
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Abstract

A continuous microfluidic glycosylation strategy that requires no chromatography between steps and significantly expedites glycosylation chemistry is described. This practical approach incorporates the advantages of imidazolium-based chromatography-free purification and in situ mass spectrometry reaction monitoring to achieve fast reaction optimization and shorter reaction times. We demonstrate the utility of this strategy in the synthesis of a series of glycoside targets, including an α-(1,6)-trimannoside and a branched Man oligomannoside, within 1 day.

References
1.
Ghirardello M, Zhang Y, Voglmeir J, Galan M . Recent applications of ionic liquid-based tags in glycoscience. Carbohydr Res. 2022; 520:108643. DOI: 10.1016/j.carres.2022.108643. View

2.
Ganesh N, Fujikawa K, Tan Y, Stine K, Demchenko A . HPLC-assisted automated oligosaccharide synthesis. Org Lett. 2012; 14(12):3036-9. PMC: 3426652. DOI: 10.1021/ol301105y. View

3.
Ramos-Soriano J, de la Fuente M, de la Cruz N, Figueiredo R, Rojo J, Reina J . Straightforward synthesis of Man, the relevant epitope of the high-mannose oligosaccharide. Org Biomol Chem. 2017; 15(42):8877-8882. DOI: 10.1039/c7ob02286g. View

4.
Yalamanchili S, Nguyen T, Zsikla A, Stamper G, DeYong A, Florek J . Automated, Multistep Continuous-Flow Synthesis of 2,6-Dideoxy and 3-Amino-2,3,6-trideoxy Monosaccharide Building Blocks. Angew Chem Int Ed Engl. 2021; 60(43):23171-23175. PMC: 8511145. DOI: 10.1002/anie.202109887. View

5.
Cole K, Groh J, Johnson M, Burcham C, Campbell B, Diseroad W . Kilogram-scale prexasertib monolactate monohydrate synthesis under continuous-flow CGMP conditions. Science. 2017; 356(6343):1144-1150. DOI: 10.1126/science.aan0745. View