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808512

Sigma-Aldrich

γ-[(Propargyl)-imido]-ATP sodium salt

Synonym(s):

Adenosine-5’-[γ-(propargyl)-imido]triphosphate sodium salt

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About This Item

Empirical Formula (Hill Notation):
C13H19N6O12P3 · xNa+
Molecular Weight:
544.24 (free acid basis)
UNSPSC Code:
12352200
PubChem Substance ID:
329769104
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

NC1=NC=NC2=C1N=CN2[C@H]3O[C@H](COP(OP(O)(OP(O)(NCC#C)=O)=O)(O)=O)[C@@H](O)[C@H]3O

InChI

1S/C13H19N6O12P3/c1-2-3-18-32(22,23)30-34(26,27)31-33(24,25)28-4-7-9(20)10(21)13(29-7)19-6-17-8-11(14)15-5-16-12(8)19/h1,5-7,9-10,13,20-21H,3-4H2,(H,24,25)(H,26,27)(H2,14,15,16)(H2,18,22,23)/t7-,9-,10-,13?/m1/s1

InChI key

PIPOEUYSJJTELD-RJNFYWFKSA-N

Application

Lee, et al,. reported a non-radioactive version of in vitro phosphorylation where γ-[(Propargyl)-imido]-ATP (compound 1) was successfully used instead of γ-32P-modified ATP to phosphorylate GST-tagged recombinant p27kip1 with protein kinase cdk2. The phosphorylated, alkyne-modified protein substrate can be labeled with azides of biotin or fluorescent dyes using Cu(I)-catalyzed click chemistry.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Sarah E Lee et al.
Bioorganic & medicinal chemistry letters, 19(14), 3804-3807 (2009-05-05)
We hereby present a simple yet novel chemical synthesis of a family of gamma-modified ATPs bearing functional groups on the gamma-phosphate that are amenable to further derivatization by highly selective chemical manipulations (e.g., click chemistry, Staudinger ligations). A preliminary screen

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