Stereoselective synthesis of a novel apio analogue of neplanocin A as potential S-adenosylhomocysteine hydrolase inhibitor

Org Lett. 2002 Oct 3;4(20):3501-3. doi: 10.1021/ol026624m.

Abstract

A total synthesis of apio-neplanocin A, which combines properties of apio nucleoside and neplanocin A and is a potential inhibitor of S-adenosylhomocysteine hydrolase, was accomplished starting from D-ribose via stereoselective hydroxymethylation and RCM reaction. [reaction: see text]

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Adenosine / analogs & derivatives*
  • Adenosine / chemical synthesis*
  • Adenosine / chemistry*
  • Adenosylhomocysteinase
  • Enzyme Inhibitors / chemical synthesis*
  • Enzyme Inhibitors / chemistry*
  • Hydrolases / antagonists & inhibitors*
  • Molecular Structure
  • Stereoisomerism

Substances

  • Enzyme Inhibitors
  • neplanocin A
  • Hydrolases
  • Adenosylhomocysteinase
  • Adenosine