Synthesis of deuterated-BCX-1777, a potent inhibitor of purine nucleoside phosphorylase

✍ Scribed by Hollis S. Kezar III; Tracy L. Hutchison; Peter C. Tyler; Philip E. Morris Jr.

• Publisher: John Wiley and Sons
• Year: 2002
• Tongue: French
• Weight: 112 KB
• Volume: 45
• Category: Article
• ISSN: 0022-2135
• DOI: 10.1002/jlcr.533

✦ Synopsis

Abstract

BCX‐1777, a novel inhibitor of the enzyme purine nucleoside phosphorylase, mimics the charged ribosyl oxocarbenium ion formed during the transition state of the enzyme‐catalyzed CN bond cleavage of nucleosides. BCX‐1777 is a slow‐onset, tight‐binding inhibitor with a K~i~^*^ of 23 pM and is one of the most potent inhibitors known for the enzyme. In support of our BCX‐1777 program, a mass spectrometric assay has been developed utilizing 5′‐[^2^H]‐BCX‐1777 as an internal standard. The synthesis of 5′‐[^2^H]‐BCX‐1777 is described in this report. Copyright © 2002 John Wiley & Sons, Ltd.