Stereoselectivity of binding of alpha-(N-benzylamino)benzylphosphonic acids to prostatic acid phosphatase.

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Vovk AI, Mischenko IM, Tanchuk VY, Kachkovskii GA, Sheiko SY, Kolodyazhnyi OI, Kukhar VP

Stereoselectivity of binding of alpha-(N-benzylamino)benzylphosphonic acids to prostatic acid phosphatase.

Bioorg Med Chem Lett. 2008 Aug 15;18(16):4620-3. doi: 10.1016/j.bmcl.2008.07.021. Epub 2008 Jul 10.

PubMed ID

18672366 [ View in PubMed

]

Abstract

The inhibition effects of enantiomerically pure alpha-(N-benzylamino)benzylphosphonic acids and their derivatives on human prostatic acid phosphatase have been investigated. As expected, (R)-alpha-(N-benzylamino)benzylphosphonic acid demonstrated higher affinity for the enzyme than (S)-enantiomer. At the same time, (1R,2S)-phenyl[(1-phenylethyl)amino]methylphosphonic acid was found to be a significantly weaker inhibitor than its (1S,2R)-analogue. The enantioselectivity has been explained using a molecular modeling approach by computational docking of inhibitors into active center of prostatic acid phosphatase.

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Binding Properties

Drug	Target	Property	Measurement	pH	Temperature (°C)
Alpha-Benzyl-Aminobenzyl-Phosphonic Acid	Prostatic acid phosphatase	IC 50 (nM)	4	N/A	N/A	Details