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

Guo-Biao Zhu; Chen Guo; Xue-Lian Ren; Ming-Zhe Li; Di-Ya Lu; Xi-Le Hu; He Huang; Tony D. James; Xiao-Peng He

doi:10.1039/D4OB01563K

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

Guo-Biao Zhu,

‡^a Chen Guo,

‡^a Xue-Lian Ren,

^fg Ming-Zhe Li,^c Di-Ya Lu,^c Xi-Le Hu,

*^a He Huang,

*^fg Tony D. James

*^de and Xiao-Peng He

*^abc

Author affiliations

* Corresponding authors

^a 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
E-mail: xlhu@ecust.edu.cn, xphe@ecust.edu.cn

^b The International Cooperation Laboratory on Signal Transduction, Eastern Hepatobiliary Surgery Hospital, National Center for Liver Cancer, Shanghai 200438, China

^c Shanghai World Foreign Language Academy, No. 400 Baihua Street, Shanghai 200233, China

^d Department of Chemistry, University of Bath, Bath, UK
E-mail: t.d.james@bath.ac.uk

^e School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang 453007, China

^f State Key Laboratory of Chemical Biology, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai 201203, China
E-mail: hhuang@simm.ac.cn

^g School of Pharmaceutical Science and Technology, Hangzhou Institute for Advanced Study, University of Chinese Academy of Sciences, Hangzhou 310024, China

Abstract

We have synthesized two sialic acid derivatives substituted with an ortho-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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Article information

DOI: https://doi.org/10.1039/D4OB01563K
Article type: Paper
Submitted: 25 Sep 2024
Accepted: 24 Oct 2024
First published: 04 Nov 2024
This article is Open Access

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Org. Biomol. Chem., 2024,22, 9403-9407

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

G. Zhu, C. Guo, X. Ren, M. Li, D. Lu, X. Hu, H. Huang, T. D. James and X. He, Org. Biomol. Chem., 2024, 22, 9403 DOI: 10.1039/D4OB01563K

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Organic & Biomolecular Chemistry

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

Abstract

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

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