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Sigma-Aldrich

γ-[(6-Azidohexyl)-imido]-ATP sodium salt

Synonym(s):

γ-[(6-Azidohexyl)-imido]-adenosine-5’-triphosphate sodium salt

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About This Item

Empirical Formula (Hill Notation):
C16H28N9O12P3 · xNa+
Molecular Weight:
631.37 (free acid basis)
UNSPSC Code:
12352200
PubChem Substance ID:
329769105
NACRES:
NA.22

Assay

≥95% (HPLC)

Quality Level

200

form

powder

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(NCCCCCCN=[N+]=[N-])(O)=O)=O)=O)O[C@@H]1N2C=NC3=C2N=CN=C3N

InChI

1S/C16H28N9O12P3/c17-14-11-15(20-8-19-14)25(9-21-11)16-13(27)12(26)10(35-16)7-34-39(30,31)37-40(32,33)36-38(28,29)23-6-4-2-1-3-5-22-24-18/h8-10,12-13,16,26-27H,1-7H2,(H,30,31)(H,32,33)(H2,17,19,20)(H2,23,28,29)/t10-,12-,13-,16?/m1/s1

InChI key

FZLLGYSKHRTLRX-AARXTDBFSA-N

Application

Lee, et al., reported a non-radioactive version of in vitro phosphorylation where γ-[(6-Azidohexyl)-imido]-ATP (compound 6) was successfully used instead of γ-32P-modified ATP to phosphorylate GST-tagged recombinant p27kip1 with protein kinase cdk2. The phosphorylated, azide-modified protein substrate can be labeled with alkynes of biotin or fluorescent dyes using Cu(I)-catalyzed click chemistry or DBCO-containing biotin or fluorescent dyes using Cu(I)-free click chemistry.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

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Sigma-Aldrich

A2383

Adenosine 5′-triphosphate disodium salt hydrate

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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