ATP-polyamine-biotin

• CAT Number: I013777
• CAS Number: 1800401-93-7
• Molecular Formula: C32H58N11O14P3S
• Molecular Weight: 945.85
• Purity: ≥95%
• Synonyms: N-[3-[4-[3-[5-[(3aS,4S,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoylamino]propyl-methylamino]butyl-methylamino]propyl]-[[[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-hydroxyphosphoryl]oxyphosphonamidic acid
• InChI: InChI=1S/C32H58N11O14P3S/c1-41(15-7-11-34-24(44)10-4-3-9-23-25-21(18-61-23)39-32(47)40-25)13-5-6-14-42(2)16-8-12-38-58(48,49)56-60(52,53)57-59(50,51)54-17-22-27(45)28(46)31(55-22)43-20-37-26-29(33)35-19-36-30(26)43/h19-23,25,27-28,31,45-46H,3-18H2,1-2H3,(H,34,44)(H,50,51)(H,52,53)(H2,33,35,36)(H2,38,48,49)(H2,39,40,47)/t21-,22+,23-,25-,27+,28+,31+/m0/s1
• InChIKey: MODMQMYTNMWWCS-MCINONILSA-N
• SMILES: CN(CCCCN(C)CCCNP(=O)(O)OP(=O)(O)OP(=O)(O)OCC1C(C(C(O1)N2C=NC3=C(N=CN=C32)N)O)O)CCCNC(=O)CCCCC4C5C(CS4)NC(=O)N5

ATP-polyamine-biotin, the first cell-permeable ATP analogue, is an efficient kinase cosubstrate. ATP-polyamine-biotin promotes biotin labeling of kinase substrates in live cells[1].
ATP-polyamine-biotin (APB) is incubated with PKA kinase and full-length protein substrate, myelin basic protein (MBP). Biotinylation was observed only in presence of kinase. In addition, MBP biotinylation was lost in the absence of ATP-polyamine-biotin, in presence of the kinase inhibitor staursporine or upon incubation with acid due to cleavage of phosphoramidate bond. Biotinylated kemptide product is observed only in the presence of APB cosubstrate[1].

Reference

[1]. Fouda AE, et al. A Cell-Permeable ATP Analogue for Kinase-Catalyzed Biotinylation. Angew Chem Int Ed Engl. 2015 Aug 10;54(33):9618-21.
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