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

Research output: Contribution to journal › Article › peer-review

1 Citation (SciVal)

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.

Original language	English
Pages (from-to)	9403-9407
Number of pages	5
Journal	Organic and Biomolecular Chemistry
Volume	22
Issue number	48
Early online date	4 Nov 2024
DOIs	https://doi.org/10.1039/d4ob01563k
Publication status	Published - 28 Dec 2024

Data Availability Statement

All data associated with this study have been included in either the manuscript or the supplementary file associated with the manuscript.

Funding

The authors thank the Natural National Science Foundation of China (NSFC) (No. 92253306, 82130099 and 22108077), the Shanghai Municipal Science and Technology Major Project (No. 2018SHZDZX03), the International Cooperation Program of Shanghai Science and Technology (No. 23490711600), the Fundamental Research Funds for the Central Universities (222201717003), the Programme of Introducing Talents of Discipline to Universities (B16017), the Open Funding Project of the State Key Laboratory of Bioreactor Engineering, State Key Laboratory of Drug Research (SKLDR-2023-KF-10) and Ministry of Education Key Laboratory on Signaling Regulation and Targeting Therapy of Liver Cancer (Naval Medical University) (Grant. 2023-MEKLLC-MS/ZD-00*) for financial support. TDJ wishes to thank the University of Bath and the Open Research Fund of the School of Chemistry and Chemical Engineering, Henan Normal University (2020ZD01) for support. The Research Center of Analysis and Test of East China University of Science and Technology is gratefully acknowledged for assistance in analytical experiments.

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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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.",

author = "Zhu, {Guo Biao} and Chen Guo and Ren, {Xue Lian} and Li, {Ming Zhe} and Lu, {Di Ya} and Hu, {Xi Le} and He Huang and James, {Tony D.} and He, {Xiao Peng}",

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AU - Zhu, Guo Biao

AU - Guo, Chen

AU - Ren, Xue Lian

AU - Li, Ming Zhe

AU - Lu, Di Ya

AU - Hu, Xi Le

AU - Huang, He

AU - James, Tony D.

AU - He, Xiao Peng

PY - 2024/12/28

Y1 - 2024/12/28

N2 - 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.

AB - 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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DO - 10.1039/d4ob01563k

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ER -

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

Abstract

Data Availability Statement

Funding

ASJC Scopus subject areas

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