Non-natural sialic acid derivatives with -nitrobenzyl alcohol substituents for light-mediated protein conjugation and cell imaging.

Org Biomol Chem

Key Laboratory for Advanced Materials and Joint International Research Laboratory of Precision Chemistry and Molecular Engineering, Feringa Nobel Prize Scientist Joint Research Center, Frontiers Center for Materiobiology and Dynamic Chemistry, School of Chemistry and Molecular Engineering, East China University of Science and Technology, 130 Meilong RD, Shanghai 200237, China.

Published: December 2024

We have synthesized two sialic acid derivatives substituted with an -nitrobenzyl alcohol (o-NBA) group that can undergo light-mediated conjugation with primary amines at their 5- or 9-carbon position. The o-NBA derivatives were shown to react with multiple lysine residues of human serum albumin (HSA) when exposed to 365 nm light irradiation within 10 min. The resulting sugar conjugates were characterized by mass spectroscopy and used for fluorescence-based cell imaging.

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http://dx.doi.org/10.1039/d4ob01563kDOI Listing

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