Enzymatic Synthesis of Trideuterated Sialosides

Enzymatic Synthesis of Trideuterated Sialosides

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. Usin...

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Bibliographic Details
Published in:Molecules (Basel, Switzerland) Switzerland), 2019-04, Vol.24 (7), p.1368
Main Authors: Cai, Zhi-P, Conway, Louis P, Huang, Ying Y, Wang, Wen J, Laborda, Pedro, Wang, Ting, Lu, Ai M, Yao, Hong L, Huang, Kun, Flitsch, Sabine L, Liu, Li, Voglmeir, Josef
Format: Article
Language:eng
Subjects:
Acids
Aldehydes
Cell surface
Chromatography
Deuteration
Deuterium
Eggs
Enzymatic synthesis
Enzymes
Glycoconjugates
Heavy water
isotope labeled carbohydrates
Lipids
Liquid chromatography
Meat
Monosaccharides
N-glycolylneuraminic acid
NMR
Nuclear magnetic resonance
sialic acid biosynthesis
sialic acid quantification
Sialic acids
Spectrometry
Synthesis
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Summary: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.
ISSN:1420-3049
1420-3049