N-Glycolylneuraminic acid

N-Glycolylneuraminic acid (Neu5Gc) is a nonhuman sialic acid molecule synthesized in pigs but not in humans, that has a role as a mammalian metabolite and an antigen. This hydroxylated form of sialic acid, specifically N-acetylneuraminic acid, features a glycolyl substituent on nitrogen and a beta-configuration at the anomeric center. The biosynthesis of N-glycolylneuraminic acid involves the enzymatic activity of cytidine monophosphate-N-acetylneuraminate (CMP-Neu5Ac) hydroxylase.
In humans, the absence of endogenous production results from a gene mutation affecting CMP-Neu5Ac hydroxylase, the enzyme responsible for converting N-acetylneuraminic acid into Neu5Gc. However, Neu5Gc can accumulate in human cells through external ingestion from dietary sources like red meat and dairy products. N-Glycolylneuraminic acid is a versatile compound that finds application in cell biology, metabolomics and biochemical research

N-Glycolylneuraminic acid has been used:

• as a sugar in microtiter biofilm methodologic approach for the enhancement of biofilm formation
• as a standard for the determination of sialic acids in the nervous system of silkworm and to find the variations of sialic acids among different developmental stages.
• as a standard in the high-performance liquid chromatography (HPLC) analyses to detect the molecular species of sialic acid (Sia) species using 1,2-diamino-4,5-methylenedioxy-benzene (DMB) as a fluorogenic compound

N-Glycolylneuraminic acid (Neu5Gc) functions as an important tool for profiling anti-Neu5Gc antibodies and sialic acid-binding proteins.

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