Synthesis of an alpha-aminophosphonate nucleoside as an inhibitor of S-adenosyl-L-homocysteine hydrolase

Bioorg Med Chem Lett. 2002 Feb 11;12(3):457-60. doi: 10.1016/s0960-894x(01)00789-2.

Abstract

A phosphonic acid analogue of S-adenosyl-L-homocysteine was prepared by a novel method and the epimeric mixture separated. Preliminary studies indicate that each epimer causes time-dependent inactivation of S-adenosyl-L-homocysteine hydrolase, however each presented distinct kinetic characteristics.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Adenosine / analogs & derivatives
  • Adenosine / chemical synthesis*
  • Adenosine / pharmacology*
  • Adenosylhomocysteinase
  • Animals
  • Drug Design
  • Enzyme Inhibitors / chemical synthesis*
  • Enzyme Inhibitors / pharmacology*
  • Hydrolases / antagonists & inhibitors*
  • Kinetics
  • Organophosphonates / chemical synthesis*
  • Organophosphonates / pharmacology*
  • Rats
  • Recombinant Proteins
  • S-Adenosylhomocysteine / analogs & derivatives*
  • S-Adenosylhomocysteine / pharmacology*
  • Stereoisomerism
  • Structure-Activity Relationship

Substances

  • 5'-deoxy-5'-((3-amino-3-phosphonopropyl)thio)adenosine
  • Enzyme Inhibitors
  • Organophosphonates
  • Recombinant Proteins
  • S-Adenosylhomocysteine
  • Hydrolases
  • Adenosylhomocysteinase
  • Adenosine