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808490

Sigma-Aldrich

N6-Propargyl-ATP sodium salt

Synonym(s):

(N6pATP) sodium salt, N6-Propargyl-adenosine-5’-triphosphate sodium salt

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About This Item

Empirical Formula (Hill Notation):
C13H18N5O13P3 · xNa+
Molecular Weight:
545.23 (free acid basis)
UNSPSC Code:
12352106
PubChem Substance ID:
329769102
NACRES:
NA.22

Assay

≥95% (HPLC)

Quality Level

200

form

solid

reaction suitability

reaction type: click chemistry

solubility

10 mM Tris-HCl, pH 7.5: soluble

shipped in

wet ice

storage temp.

−20°C

SMILES string

O[C@@H]([C@H]1O)[C@@H](COP(O)(OP(O)(OP(O)(O)=O)=O)=O)O[C@@H]1N2C=NC3=C2N=CN=C3NCC#C

InChI

1S/C13H18N5O13P3/c1-2-3-14-11-8-12(16-5-15-11)18(6-17-8)13-10(20)9(19)7(29-13)4-28-33(24,25)31-34(26,27)30-32(21,22)23/h1,5-7,9-10,13,19-20H,3-4H2,(H,24,25)(H,26,27)(H,14,15,16)(H2,21,22,23)/t7-,9-,10-,13?/m1/s1

InChI key

MUOIWXPACQCYQC-RJNFYWFKSA-N

Application

N6-Propargyl-ATP is suitable for in vitro AMPylation of proteins as well as in vitro polyadenylation of RNA. The resulting alkyne-functionalized protein or RNA can be processed using Cu(I)-catalyzed click chemistry to attach azide-labeled molecules. This gives options such as introduction of a biotin group for purification tasks, introduction of a fluorescent group for detection, or crosslinking to other azide-functionalized biomolecules.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Sigma-Aldrich

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Markus Grammel et al.
Chembiochem : a European journal of chemical biology, 13(8), 1112-1115 (2012-04-20)
A versatile "clickable" nucleoside: Metabolic labeling of cells is useful in studying the dynamics of biological molecules. N(6) pA can be utilized by all three mammalian RNA polymerases, as well as poly(A) polymerase. Because of its alkyne modification, RNA labeled
A new chemical handle for protein AMPylation at the host-pathogen interface.
Malgorzata Broncel et al.
Chembiochem : a European journal of chemical biology, 13(2), 183-185 (2012-01-04)
Markus Grammel et al.
Journal of the American Chemical Society, 133(43), 17103-17105 (2011-09-29)
Protein AMPylation is an emerging post-translational modification, which plays key roles in bacterial pathogenesis and cell biology. Enzymes with AMPylation activity, referred to as AMPylators, have been identified in several bacterial pathogens and eukaryotes. To facilitate the study of this

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