Highly potent metabolic label of sialylation
|Synonyms:||Ac5SiaPoc; Ac5Neu5NPoc; Ac5SiaPoc; Ac5SiaPoc|
|Tags:||Alkyne, Bioorthogonal chemistry, Metabolic label, Neuraminic acid, Neuraminidase, Sialic acid, Sialidase|
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Unnatural sialic acid analog for metabolic labeling. Contains a Poc group for “click” chemistry. P-Neu5NPoc is passively taken-up by cells and incorporated in cell surface sialoglycans. Azide reagents can be reacted with the Poc group on live and fixed cells.1 These azide can be modified with an affinity tag or fluorophore for example. Small molecules can also be attached to enhance the binding to Siglec receptors.2 Beyond its application of P-Neu5NPoc for click chemistry, incorporation of this unnatural derivative also led to resistance to sialidases.3 This has been studied in the context of viral infection. In this study, the use of P-Neu5NPoc in host cells led to a decreased influenza infection by blocking its neuraminidase. In contrast, another derivative P-Neu5NAz is susceptible to neuraminidase cleavage and does not desturb sialoglycan turnover.
Mode of action
P-Neu5NPoc is passively taken-up by mammalian cells and converted into its CMP-SiaPoc derivative. This is used as a donor substrate for sialyltransferase enzymes and transferred to O-, N-glycans and glycolipids. P-Neu5NPoc is a much more efficient metabolic label of sialic acid than ManNAc based derivative and also less toxic.1, 4
Metabolic labeling of sialoglycans for isolation, visualization and to improve Siglec binding
P-Neu5NPoc is soluble in DMSO and PBS and is added to cell culture from a stock solution. Incubation of the cells with P-SiaPoc for 3 days in needed to achieve the maximal metabolic incorporation. Three days is needed to achieve the turnover of sialylated glycans to achieve maximal metabolic incorporation.
CAS No.: NA
Chemical formula: C24H31NO15
Molecular weight: 573.17
Purity: > 95%
Identity: 1H NMR
Shipping temperature: 20°C
Storage temperature: 0°C
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