N⁵-Phosphonoacetyl-L-ornithine (PALO): A convenient synthesis and investigation of influence on regulation of amino acid biosynthetic genes in Saccharomyces cerevisiae

Authors

Brad Johnson, University of Nebraska-LincolnFollow
Rachel Steadman, University of Nebraska-Lincoln
Krista D. Patefield, University of Nebraska-Lincoln
Jeffrey J. Bunker, University of Nebraska-Lincoln
Audrey L. Atkin, University of Nebraska - LincolnFollow
Patrick Dussault, University of Nebraska-LincolnFollow

Document Type

Article

Date of this Version

4-2011

Comments

Published in Bioorganic & Medicinal Chemistry Letters 21:8 (April 15, 2011), pp. 2351–2353; doi: 10.1016/j.bmcl.2011.02.081 Copyright © 2011 Elsevier Ltd. Used by permission.

Abstract

A scalable four-step synthesis of the ornithine transcarbamylase inhibitor N⁵-phosphonoacetyl-L-ornithine (PALO) is achieved through boroxazolidinone protection of ornithine. Investigations in the model organism Saccharomyces cerevisiae found that, in contrast to a previous report, PALO did not influence growth rate or expression of genes involved in arginine metabolism.