0

Stereoselectivity of Binding of alpha-(N-benzylamino)benzylphosphonic Acids to Prostatic Acid Phosphatase

Andriy I Vovk, Iryna M Mischenko, Vsevolod Yu Tanchuk, Georgiy A Kachkovskii, Sergiy Yu Sheiko, Oleg I Kolodyazhnyi, Valery P Kukhar

Bioorg Med Chem Lett. 2008 Aug 15;18(16):4620-3.

PMID: 18672366

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.

Chemicals Related in the Paper:

Catalog Number Product Name Structure CAS Number Price
AP6881578 Benzylphosphonic acid Benzylphosphonic acid 6881-57-8 Price
qrcode