Enzymatic Synthesis of Trideuterated Sialosides
by
Zhi-P. Cai 1,†, Louis P. Conway 1,†, Ying Y. Huang 1,†, Wen J. Wang 1,†, Pedro Laborda 2, Ting Wang 1, Ai M. Lu 3, Hong L. Yao 1, Kun Huang 4, Sabine L. Flitsch 4, Li Liu 1,* and Josef Voglmeir 1,*
Zhi-P. Cai 1,†, Louis P. Conway 1,†, Ying Y. Huang 1,†, Wen J. Wang 1,†, Pedro Laborda 2, Ting Wang 1, Ai M. Lu 3, Hong L. Yao 1, Kun Huang 4, Sabine L. Flitsch 4, Li Liu 1,* and Josef Voglmeir 1,*
1
Glycomics and Glycan Bioengineering Research Center (GGBRC), College of Food Science and Technology, Nanjing Agricultural University, Nanjing 210095, China
2
School of Life Sciences, Nantong University, Nantong 226019, China
3
College of Sciences, Nanjing Agricultural University, Nanjing 210095, China
4
Manchester Institute of Biotechnology, University of Manchester, Manchester M1 7DN, UK
*
Authors to whom correspondence should be addressed.
†
These authors contributed equally to this work.
Academic Editor: Lothar Elling
Molecules 2019, 24(7), 1368; https://doi.org/10.3390/molecules24071368
Received: 28 February 2019 / Revised: 29 March 2019 / Accepted: 2 April 2019 / Published: 8 April 2019
(This article belongs to the Special Issue Synthesis and Biological Applications of Glycoconjugates Ⅱ)
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.
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Keywords:
N-glycolylneuraminic acid; isotope labeled carbohydrates; sialic acid quantification; sialic acid biosynthesis
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited
MDPI and ACS Style
Cai, Z.-P.; Conway, L.P.; Huang, Y.Y.; Wang, W.J.; Laborda, P.; Wang, T.; Lu, A.M.; Yao, H.L.; Huang, K.; Flitsch, S.L.; Liu, L.; Voglmeir, J. Enzymatic Synthesis of Trideuterated Sialosides. Molecules 2019, 24, 1368.
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