P-Neu5NPoc

Highly potent metabolic label of sialylation

Product ID:	SV2431
Synonyms:	Ac₅SiaPoc; Ac₅Neu5NPoc; Ac₅SiaPoc; Ac₅SiaPoc
Tags:	Alkyne, Bioorthogonal chemistry, Metabolic label, Neuraminic acid, Neuraminidase, Sialic acid, Sialidase

Product	Price	Estimated Shipping Time	Purchase
P-Neu5NPoc - 10 mg	€250.00	1-3 days	P-Neu5NPoc quantity
P-Neu5NPoc - 25 mg	€425.00	1-3 days	P-Neu5NPoc quantity
P-Neu5NPoc - 100 mg	€1,100.00	1-3 days	P-Neu5NPoc quantity

Function

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

Applications

Metabolic labeling of sialoglycans for isolation, visualization and to improve Siglec binding
Handling

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.
Chemical Information

CAS No.: NA
SMILES: O=C(OCC#C)N[C@H]1[C@H]([C@H](OC(C)=O)[C@H](OC(C)=O)COC(C)=O)OC(C(OC)=O)(OC(C)=O)C[C@@H]1OC(C)=O
Chemical formula: C₂₄H₃₁NO₁₅
Molecular weight: 573.17
Purity: > 95%
Identity: ¹H NMR
Shipping temperature: 20°C
Storage temperature: -20°C

Structure	Name	Functions	Description	Purchase
	Neu5Ac3F	Inhibitor	Metabolic inhibitor of sialylation for active uptake	P-Neu5NPoc quantity
Structure Description Metabolic inhibitor of sialylation for active uptake Functions Inhibitor Purchase P-Neu5NPoc quantity
	P-GlcNAlk	Metabolic label	Selective metabolic label of GlcNAc residues	P-Neu5NPoc quantity
Structure Description Selective metabolic label of GlcNAc residues Functions Metabolic label Purchase P-Neu5NPoc quantity
	Neu5NPoc	Metabolic label	Metabolic label of sialylation for active uptake	P-Neu5NPoc quantity
Structure Description Metabolic label of sialylation for active uptake Functions Metabolic label Purchase P-Neu5NPoc quantity
	P-GlcNPoc	Metabolic label	Metabolic label of GlcNAc residues	P-Neu5NPoc quantity
Structure Description Metabolic label of GlcNAc residues Functions Metabolic label Purchase P-Neu5NPoc quantity
	Neu5Ac9Az	Metabolic label	Metabolic label of sialic acids	P-Neu5NPoc quantity
Structure Description Metabolic label of sialic acids Functions Metabolic label Purchase P-Neu5NPoc quantity

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