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

作者信息

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

机构信息

Institute of Bioorganic Chemistry and Petrochemistry, National Academy of Sciences of Ukraine, Murmanska, 1, 02660, Kyiv-94, Ukraine.

出版信息

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

DOI:10.1016/j.bmcl.2008.07.021

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.

摘要