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Molecules. 2019 Apr 8;24(7). pii: E1368. doi: 10.3390/molecules24071368.

Enzymatic Synthesis of Trideuterated Sialosides.

Author information

1
Glycomics and Glycan Bioengineering Research Center (GGBRC), College of Food Science and Technology, Nanjing Agricultural University, Nanjing 210095, China. caizhipeng@njau.edu.cn.
2
Glycomics and Glycan Bioengineering Research Center (GGBRC), College of Food Science and Technology, Nanjing Agricultural University, Nanjing 210095, China. t2015030@njau.edu.cn.
3
Glycomics and Glycan Bioengineering Research Center (GGBRC), College of Food Science and Technology, Nanjing Agricultural University, Nanjing 210095, China. 2014108037@njau.edu.cn.
4
Glycomics and Glycan Bioengineering Research Center (GGBRC), College of Food Science and Technology, Nanjing Agricultural University, Nanjing 210095, China. 2014108004@njau.edu.cn.
5
School of Life Sciences, Nantong University, Nantong 226019, China. pedro.laborda@njau.edu.cn.
6
Glycomics and Glycan Bioengineering Research Center (GGBRC), College of Food Science and Technology, Nanjing Agricultural University, Nanjing 210095, China. wangting@njau.edu.cn.
7
College of Sciences, Nanjing Agricultural University, Nanjing 210095, China. luaimin@njau.edu.cn.
8
Glycomics and Glycan Bioengineering Research Center (GGBRC), College of Food Science and Technology, Nanjing Agricultural University, Nanjing 210095, China. 2013208011@njau.edu.cn.
9
Manchester Institute of Biotechnology, University of Manchester, Manchester M1 7DN, UK. kun.huang-3@manchester.ac.uk.
10
Manchester Institute of Biotechnology, University of Manchester, Manchester M1 7DN, UK. sabine.flitsch@manchester.ac.uk.
11
Glycomics and Glycan Bioengineering Research Center (GGBRC), College of Food Science and Technology, Nanjing Agricultural University, Nanjing 210095, China. lichen.liu@njau.edu.cn.
12
Glycomics and Glycan Bioengineering Research Center (GGBRC), College of Food Science and Technology, Nanjing Agricultural University, Nanjing 210095, China. josef.voglmeir@njau.edu.cn.

Abstract

Sialic acids are a family of acidic monosaccharides often found on the termini of cell surface proteins or lipid glycoconjugates of higher animals. Herein we describe the enzymatic synthesis of the two isotopically labeled sialic acid derivatives d₃-X-Gal-α-2,3-Neu5Ac and d₃-X-Gal-α-2,3-Neu5Gc. Using deuterium oxide as the reaction solvent, deuterium atoms could be successfully introduced during the enzymatic epimerization and aldol addition reactions when the sialosides were generated. NMR and mass spectrometric analyses confirmed that the resulting sialosides were indeed tri-deuterated. These compounds may be of interest as internal standards in liquid chromatography/mass spectrometric assays for biochemical or clinical studies of sialic acids. This was further exemplified by the use of this tri-deuterated sialosides as internal standards for the quantification of sialic acids in meat and egg samples.

KEYWORDS:

N-glycolylneuraminic acid; isotope labeled carbohydrates; sialic acid biosynthesis; sialic acid quantification

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