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206646-04-0

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Acyclic phosphonate nucleotides and human adenylate kinases: Impact of a borano group on α-P position
Adenylate kinases are involved in the activation of antiviral drugs such as the acyclic phosphonates analogs PMEA and (R)PMPA. We examine the in vitro phosphorylation of PMEA and PMPA bearing a borano- or a H- group on the phosphorus atom. The α-borano or α-H on PMEA and PMPA were detrimental to the activity of recombinant human AMP kinases 1 and 2. Docking PMEA to the active site of AMP kinase 1 indicated that the borano group may prevent two conserved critical Arg interactions with the α-phosphate, resulting in substrate bad positioning. Copyright Taylor & Francis Group, LLC.
Topalis,Alvarez,Barral,Munier-Lehmann,Schneider,Veron,Guerreiro,Mulard,El-Amri,Canard,Deville-Bonne
p. 319 - 331
(2008)
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Phosphorylation of purine (phosphonomethoxy)alkyl derivatives by mitochondrial AMP kinase (AK2 type) from L1210 cells
Substrate activity of purine (phosphonomethoxy)alkyl derivatives towards mitochondrial AMP kinase (AK2 type) from L1210 cells was studied. The native AMP kinase, purified nearly to homogeneity, is a monomer with molecular weight 26 kDa. The purified AMP kinase is specific for natural adenine nucleotides (AMP and dAMP) as phosphate acceptors but has a broad specificity to nucleoside 5′-triphosphates as phosphate donors. In addition to adenine acyclic nucleotide analogues, the enzyme is capable of phosphorylating also analogous derivatives containing 2,6-diaminopurine moiety. Kinetic data show that the substrate activity of these acyclic nucleoside phosphonates towards AK2 isoenzyme decreases in the order (S)-HPMPA > (R)-PMPA > PMEA > PMEDAP > (S)-PMPDAP > (R)-PMPDAP ? (S)-PMPA. Acyclic nucleotide analogues do not exhibit any inhibitory activity towards AK2 isoenzyme.
Krejcova, Romana,Horska, Kvetoslava,Votruba, Ivan,Holy, Antonin
p. 1653 - 1668
(2007/10/03)

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Chemical Properties

Melting Point: >140°C (dec.)
Boiling Point: 710.5°C at 760 mmHg
Flash Point:383.5°C
Density: 2.02g/cm³
Solubility:Water
Storage Temp.:Hygroscopic, -20?C Freezer, Under Inert Atmosphere
Vapor Pressure: 3.46E-21mmHg at 25°C
PKA: 1.30±0.10(Predicted)
PSA: 258.87000
LogP: 0.76400

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